Hosted by a former Fed insider who helped close 200+ failed banks during the financial crisis, Overleveraged, Overconfident dives deep into the personalities behind finance flameouts. From hedge fund collapses to crypto pipe dreams, each episode unpacks the mix of ambition, confidence, debt, and denial that drives smart people to make interesting decisions.
Follow the Journey from Hubris to Bankruptcy
Betting on Wallstreet: Robert Campeau and the destruction of retail
Robert Campeau: the man who bought Bloomingdale’s—and broke American retail doing it From a post-war Ottawa homebuilder to a swaggering 1980s dealmaker, Robert Campeau rode junk-bond rocket fuel to snag Allied Stores (1986) and then Federated Department Stores—owner of Bloomingdale’s (1988). The plan: use iconic retailers to anchor hulking real-estate plays. The problem: interest bills that cash flow couldn’t cover. When the tide went out, the debt mountain snapped—and in January 1990, Allie...
1 Oct 2025
Quick Take: The Sonoma Scandal
Meet Kenneth Mattson is the central figure in the implosion of an alleged $400 million real estate empire that prosecutors describe as a decade-long Ponzi scheme. He faces a raft of serious federal charges, including seven counts of wire fraud, one count of money laundering, and one count of obstruction of justice, to which he has pleaded not guilty. This episode was researched and written by Cherise Lloyd. Some music was created by using UDO. You can find show notes, transcripts, and sources...
24 Sept 2025
Decades:Lira, Lies and Franklin National
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 availa...
28 Jul 2025
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 speechlessA 330-slide presentation that fee...
21 Jul 2025
Excel-lent Mistakes: A Hall of Shame
This Spreadsheet Could Ruin Your Life (And Definitely Your Bonus) You think it’s just Excel—until it’s not. In this episode of Overleveraged, Overconfident, we unpack five real-world spreadsheet fails that triggered $24 million losses, $6 billion meltdowns, government investigations, and even global austerity policies. From Barclays hiding rows in a bankruptcy deal to Fannie Mae's $1.2 billion “oops,” and JP Morgan’s $6B model built by one guy in London with a PhD and no backup plan, it’s a ...
5 Jul 2025
The Blacklist Boss: Osman Semerci’s Global CDO Meltdown and Tax Fraud Comeback
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 availa...
30 Jun 2025
The Bond King's Bad Bet
When a half-billion-dollar investment goes sideways, sometimes the cure is worse than the disease. Meet JC Flowers and John Corzine—two Goldman Sachs alumni whose friendship survived boardroom betrayals, political scandals, and a spectacular fall from grace, but couldn't survive their own hubris. After Refco's spectacular 6-day collapse wiped out $3 billion in shareholder value, private equity kingpin JC Flowers saw opportunity in the wreckage. Years later, he'd recruit his old Goldman buddy ...
23 Jun 2025
Betting the Fund: Slapshots, Subprime, and the Spectacular Fall of Phil Falcone
What happens when a small-town hockey player from Minnesota’s Iron Range swaps his stick for a Bloomberg terminal and $26 billion in other people’s money? You get Phil Falcone—the hedge fund king who shorted subprime to riches, then torched it all, borrowing from his own fund, rigging bond markets, and backing a satellite network that nearly broke GPS nationwide. This is decision deafness in action: how a man who couldn’t hear “no” went from billionaire to pitching crypto TV—with his name mis...
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