Shark Tank’s Kevin O’Leary Explains Donald Trump’s Success

TV’s “Mr. Wonderful” says that the president has deregulated the economy in a powerful way.

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For the past 10 years, the reality TV show Shark Tank has entertained and edified millions of viewers by dramatizing how entrepreneurs pitch venture capitalists. And none of the “sharks”—the investors who compete with each other to fund businesses they think will be successful—is more entertaining or edifying than Kevin O’Leary, whose signature insult to unsuccessful contestants—”You’re Dead To Me”—has become a pop culture catchphrase.

But O’Leary isn’t just a small-screen blowhard. Born and raised in Canada, the 65-year-old investor got rich by developing educational and family-oriented computer software in the 1980s and ’90s and holding firm to a gospel of thrift, savings, and reinvestment that he’s outlined in best-selling books such as Cold Hard Truth on Men, Women, and Money. Over the years, he’s diversified his investments into vineyards, storage facilities, and more, and he’s dabbled in politics, too, briefly considering a run in 2017 to head the Conservative Party in Canada. His brash nature earned him easy comparisons to Donald Trump but O’Leary, who lives in Boston, is openly free trade and pro-immigration. He’s long been in favor of marijuana legalization and gay rights and opposed to military interventionism.

Nick Gillespie sat down with O’Leary at FreedomFest, the annual gathering of libertarians in Las Vegas. They talked about why Shark Tank is so popular, why Canadian Prime Minister Justin Trudeau is so bad, and whether “democratic socialism” is really a threat to the free market capitalism that O’Leary says makes us richer and happier. They also discussed why O’Leary thinks Donald Trump has been great for the economy despite a personal style so many, including O’Leary himself, find unappealing.

Interview by Nick Gillespie. Edited by Ian Keyser. Intro by Mark McDaniel.