Kevin O'Leary's money philosophy might be built on cold, hard numbers—but even "Mr. Wonderful" has a soft spot for flashy splurges and ridiculous regrets.
Back in 2018, the "Shark Tank" star told CNBC about the time he bought himself a Porsche just because he felt like it. And when he rolled up in the new ride? His wife didn't hold back.
She took one look at the car, then at him, and hit him with the line that now haunts every joyride: "Oh no, another bald a–hole in a Porsche." O'Leary didn't flinch. "I don't care, I like the car," he said. For all his lectures about disciplined investing, this was the purchase he called the "most fun he's ever had spending money."
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But fun doesn't mean smart. That title belongs to a much less showy motto passed down from his mom: never spend the principal, only the interest. That mindset, baked in since age 5, helped O'Leary build a personal net worth reportedly north of $400 million. He could afford the Porsche ten times over—and probably did it without touching his portfolio's core.
Still, he hasn't escaped buyer's remorse. He confessed to CNBC to blowing money on a pair of wildly extravagant cowboy boots in Houston. He thought it'd help him fit in for a speech. Instead, he walked on stage in boots made of snakeskin, feathers, and bells, only to be met with what he called "horror." The boots? Still in his closet, collecting dust. "They cost a freakin' fortune."
While O'Leary can laugh off the missteps, most Americans can't afford that kind of margin for error.
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In 2025, U.S. auto‑loan debt reached roughly $1.655 trillion—making vehicle financing the second‑largest category of consumer debt after mortgages. Auto loans now represent about 9.0% of all consumer debt in the U.S. On top of that, Edmunds also found that nearly 20% of new car buyers signed up for monthly payments over $1,000.
That means a Porsche or luxury ride isn't just a showoff purchase anymore—it may eat a big chunk of monthly income for a typical household.
So yes, O'Leary's wife had a point. But when you've built your empire on royalty deals and equity plays, the occasional "bald guy in a sports car" moment comes with the territory. Just maybe skip the feathered boots next time.
Still, if your dream includes a Porsche in the driveway, snakeskin cowboy boots in the closet, or a 10-gallon hat just because it feels right—there's no shame in splurging. The key is being able to afford it without derailing everything else. That's where a trusted financial adviser comes in. Whether you're chasing horsepower or retirement goals, a little guidance can help make sure your money rides exactly where you want it to go.
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