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

"I have never in my life seen an economy like this. This is even better than the '60s. It is phenomenal. And I think [it's] primarily because of deregulation, not tax reform. My companies in California, in Texas, in Florida, in Illinois…have been set free."—Kevin O'Leary

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. Cameras by Jim Epstein and Meredith Bragg.

Photo Credits:

SMG/ZUMA Press/Newscom

Dominic Chan/ Sipa USA/ Newscom

Stefani Reynolds—CNP/MEGA/Newscom

Some highlights from the conversation (edited for clarity):

Trump "is a great entertainer."

"Great politicians, great leaders, great CEOs are phenomenal entertainers. Going back to the days of Alexander the Great, Napoleon, and Bismarck, they used to hold council at night, have big dinner parties or sit around the fire with their men and tell stories. They would tell stories of great defeats, great battles, great loves, and that would spread through the troops…and it would capture the hearts and minds of the people. Donald Trump is exactly that. He is a great entertainer."

The chance Donald Trump "doesn't get a second term…is zero."

"The chance [Trump] doesn't get a second term in my view is zero. And I'll tell you why. I don't recall in modern times when going into a second term at full employment, the incumbent of any party has ever lost their mandate ever."

"Saving baby whales is not what businesses do."

"I believe that…the DNA of a business is to provide to its constituents. Clearly, customers come number one, number two, employees, somewhere in there are the shareholders…. You who started it, you're the last. When you try and shift business's true purpose and say that it's going to save society, you will fail. Not some of the time, but 100 percent of the time. Saving baby whales is not what businesses do."

"The role of government is to provide basic services."

"I think it's the role of government to provide basic services…. I'm particularly fond of what they do in Switzerland, where they basically have multiple tiers of things like health care and support for those that are poor. What they do is they'll say, OK, if you're a wealthy Swiss citizen in Geneva and you want to get an MRI because you want one tomorrow morning at 10 o'clock, you're going to pay for it. They're going to take the proceeds of that and they're going to redeploy it into purchasing more MRI machines so those that aren't as fortunate can get free MRIs."

"Everybody's a socialist when they're young."

"I was a socialist when I was 18 years old too. I was left wing. I got my first paycheck and I saw something called tax on it. Everybody's a socialist when they're young, until they start working and they start realizing how tough it is out there and they start realizing how much money government wastes when they take half their income and taxes. And that's when you become a conservative. The older you get, the more realistic you become. And a majority of those people make the transition in their mid-twenties. That's what happens. I never worry about it."

Why he prefers investing in women-run companies.

"[Women] are very, very good at mitigating risk….I'm almost sexist in the sense that even the producers have to say to me, you've got to invest in some guys. I said, why? They don't make any money. These women made me all this money…. Why should I take risks with men who can't cope, who have testosterone sales targets they never hit, and all the rest of that stuff? I'm very biased about people that understand financial independence. Women mitigate risks. Women know how to manage time. Women set reasonable goals, have very sticky cultures in business. That's all women."

"I don't fear any innovation at all. I fear regulation."

"Capitalism over the last 200 years has destroyed many industries and reborn others. Forty years ago, you couldn't have ever dreamt that someone who sat in front of a screen and wrote code would make half a million dollars a year in their first job…. Men and women will never be replaced by machines because they'll always be finding new purpose in new problems being solved. I trust capitalism to do that. I don't fear any innovation at all. I fear regulation. I fear burdensome government. I fear that a third of every dollar raised by government through taxes is wasted in every capitalist society."