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Overleveraged, Overconfident

Podcast by Cherise

English

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About 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

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8 episodes

episode Betting on Wallstreet: Robert Campeau and the destruction of retail artwork

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, Allied and Federated plunged into Chapter 11 in what was then the largest retail bankruptcy in U.S. history. It was a masterclass in speed, leverage, and hubris. What we cover in this episode * How a self-taught developer who built Ottawa’s skyline (Place de Ville) convinced Wall Street to fund billion-dollar bids. * The Allied ($3.6B) and Federated/Bloomingdale’s ($6.6B) takeovers—and why “own the stores, own the malls” was irresistible in ’86–’88. * The cash-flow math that killed the deal: rising rates, softening sales, and ~$8B of IOUs coming due. * Fallout: courtrooms, creditors, and the eventual rebuilding of a slimmer Federated that would later become today’s Macy’s, Inc. (after bankruptcy reorg). Why it matters Campeau is the cautionary tale for every “move fast, buy big” fantasy: speed can win auctions, but debt keeps score. If your thesis relies on tomorrow’s growth to pay yesterday’s interest, you’re not running a company—you’re racing a clock. Want to know more: Going for Broke: How Robert Campeau Bankrupted the Retail Industry, Jolted the Junk Bond Market, and Brought the Booming 80s to a Crashing Halt by John Rothchild 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.

20 Oct 2025 - 21 min
episode Quick Take: The Sonoma Scandal artwork

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 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.

1 Oct 2025 - 16 min
episode Decades:Lira, Lies and Franklin National artwork

Decades:Lira, Lies and Franklin National

As we dive into six decades of American financial hubris. We'll watch the same old play unfold. Hide the losses, budge the numbers, and believe your own story until the money dries up. We'll go from the smoky back rooms of the 1970s to today's glass-walled FinTech empires, because the rules may change, but the game never does. In the early 1970s, Franklin National Bank looked like the future of American finance. Its CEO, Harold Gleason, traded a quiet Long Island thrift for a lavish Park Avenue headquarters, convinced he could transform it into an international powerhouse. His secret weapon: Michele Sindona, the Vatican’s banker with mob ties and a taste for high-stakes foreign exchange bets. This episode unpacks how Gleason’s ambition and Sindona’s schemes turned a conservative regional bank into a fragile giant—and how the façade collapsed in what was, at the time, the largest bank failure in U.S. history. Host Cherise Lloyd peels back the layers of glamor, denial, and deception that made Franklin’s rise so dazzling—and its fall so inevitable. 🔊 Listen for: * The Park Avenue move that symbolized Franklin’s “big-league” ambitions * How Sindona’s currency gambles and hidden embezzlement bled the bank dry * Why cultural swagger, from The Godfather to Wall Street fantasies, blinded regulators and investors alike Sources: St. Peter's Banker: Michele Sindona, Louigi DiFonzo [https://www.goodreads.com/author/show/49969062.Louigi_DiFonzo], Power on Earth, Nick Tosches, and NYtimes Archives, as well as others  As we dive into six decades of American financial hubris. We'll watch the same old play unfold. Hide the losses, budge the numbers, and believe your own story until the money dries up. We'll go from the smoky back rooms of the 1970s to today's glass walled FinTech empires, because the rules may change, but the game never does. As we dive into six decades of American financial hubris. We'll watch the same old play unfold. Hide the losses, budge the numbers, and believe your own story until the money dries up. We'll go from the smoky back rooms of the 1970s to today's glass walled FinTech empires, because the rules may change, but the game never does. Overleveraged, Overconfident brings you the hubris, the hidden deals, and the lessons every ambitious professional should steal—minus the meltdown. 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.

24 Sep 2025 - 55 min
episode Cafeteria Fight Club: When Billionaires Act Like 7th Graders artwork

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.

29 Jul 2025 - 57 min
episode Excel-lent Mistakes: A Hall of Shame artwork

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 masterclass in how bad inputs = career-ending outputs. If you've ever copy-pasted a formula and prayed no one noticed…this one's for you. Come for the Excel horror stories, stay for the schadenfreude. 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.

21 Jul 2025 - 42 min
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