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This is Scott Becker, the Becker Business. In the Becker Private Equity podcast, we try and bring you one to two business or market insight episodes a day. We hope you enjoy the cadence. Plus we try and bring you one interview a day with the business leader. And thank you so much for listening. We also, as an aside, always want your comments. Feel free anytime to text Scott Becker, 773-766-5322 and love to hear your comments. Today's discussion is Even the Rich go broke. So so here's the story on this, and this is just absolutely fascinating. There's a multi billionaire who recently passed away in Los Angeles, Gary Winick, highly successful, or thought of as a highly successful entrepreneur, investor and more. He'd been behind one of these big, big companies from some time ago called Global Crossing, which was intended to lay cables for the Internet and sort of be the backbone of the Internet and wiring and telephonic and everything else. But in any event, Gary got incredibly rich, or thought was thought of as incredibly rich. At one point he was thought to be worth about six and a half billion dollars, and he and his wife and family live this very lavish lifestyle. So here's what happened and here's this great complication of people that have illiquid assets, don't have actual cash and assets. So he had bought a ton of different real estate, a ton of different properties, lived a hugely lavish lifestyle, and rather than converting assets into cash to pay for it, he had borrowed against his portfolio and borrowed against his companies to live the lifestyle he was living. And this is one of the great games people play and tax advisors will actually tell you to play this game and so that you don't have to pay taxes on your net worth because as long as you keep on letting it grow and don't liquidate things, you could borrow against it. And that's what people have done to live these lavish lifestyles without paying taxes because they're not realizing gains on the assets they sell. So Gary Winnick had played this game and lived this big, big lifestyle and what the tax advisors are very bad about preaching and the money management people are very bad about preaching is that you may take on these massive debts, but if in fact your asset portfolio goes down, you could end up in disastrous spot. In a disastrous spot. So, so here's where we're at now. Gary dies with what people thought was a tremendous amount of assets, but what really happens is a lot of those assets had gone down in value, not held their value. The thing about debt, and this is why you always say that debt kills families, countries and companies, is that debt doesn't go down in value unless you pay it off. So the debt wasn't paid off, the asset value went down. Now his wife, who he left behind, sadly, you know, etc. Obviously ashamed, the whole thing now is left trying to figure out how to maintain any semblance of lifestyle and even keep themselves in the house now that the sort of house of cards has come crashing down. So whenever anybody ever tells you that leverage is the way to get rich, leverage is the way to do this, or debt is the way to do this, I would tell them the Gary Winick story. And really the concept is we're very, of course, debt adverse. I might be wealthier if I take it on more debt at different times, but at the end of the day, I'm thrilled with the situation we're in. But I do think there's a lesson here. Debt kills families, it kills companies, it kills countries. Even the rich go broke. Thank you for listening to the Becker Business, the Becker Private Equity Podcast. If you get a chance, please go online to Amazon and pre order our latest book. The hardcover of the latest book, Building Great Businesses Create Momentum, Overcome Setbacks and Scale with confidence. Thank you for listening to the Becker Business and the Becker Private Equity Podcast. Thank you very much.
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Host: Scott Becker
Episode: “Even the Rich Go Broke”
Date: December 20, 2025
This episode of the Becker Private Equity & Business Podcast, hosted by Scott Becker, delves into the theme “Even the Rich Go Broke.” Using the real-life story of billionaire Gary Winnick, Becker explores how excessive leverage and living off borrowed money can lead to financial disaster—even for those who, on paper, seem untouchable. The underlying message: debt can destroy families, companies, and countries, regardless of wealth.
Background: Gary Winnick was considered a highly successful entrepreneur and investor, known for founding Global Crossing (an ambitious Internet infrastructure company).
Perceived Wealth: At his peak, Winnick was believed to be worth about $6.5 billion. He maintained a lavish lifestyle, investing heavily in real estate and other illiquid assets.
Leverage and Lifestyle:
"…what the tax advisors are very bad about preaching and the money management people are very bad about preaching is that you may take on these massive debts, but if in fact your asset portfolio goes down, you could end up in a disastrous spot."
— Scott Becker (02:36)
The Hidden Risk:
"The thing about debt, and this is why you always say that debt kills families, countries and companies, is that debt doesn't go down in value unless you pay it off."
— Scott Becker (02:47)
Life Lesson:
On Living off Borrowed Money:
"Rather than converting assets into cash to pay for it, he had borrowed against his portfolio and borrowed against his companies to live the lifestyle he was living."
— Scott Becker (01:30)
On the Perils of Debt:
"Whenever anyone ever tells you that leverage is the way to get rich... I would tell them the Gary Winick story."
— Scott Becker (03:45)
Core Takeaway:
“Debt kills families, it kills companies, it kills countries. Even the rich go broke.”
— Scott Becker (04:03)
Scott Becker’s delivery is straightforward and cautionary, blending storytelling with practical financial wisdom. He uses real-world examples and direct language to make his points resonate, maintaining a conversational yet authoritative tone throughout the episode.
This episode is a cautionary tale for anyone tempted by the promise of leverage as a path to wealth. Scott Becker warns that true financial stability comes not from maximizing debt, but from prudent management and understanding the relentless, unchanging nature of borrowed money—even when you seem rich on paper.