Donald Trump

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 and "is a great entertainer."


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"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."

NEXT: Is Money Speech? Free Speech Rules (Episode 5)

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  1. Player at top says “this video is unavailable”. Doesn’t show in Reason TV’s uploaded videos, I suspect it was pulled.

    1. Played fine for me. Maybe you still had a script-blocker running?

    2. Watching right now

    3. Works fine for me now too, same browser. Yesterday I went to Reason TV’s youtube and couldn’t find the video, pretty sure it was on Youtube’s end.

  2. “Everybody’s a socialist when they’re young.”

    And some people NEVER grow up. Taking responsibility = maturity; it’s not always easy, but you’ll remain an infantile parasite if you don’t.

  3. What’s a little bigotry, boorishness, and belligerent ignorance there’s some deregulation (even with tariffs) and white-bread entertainment under that pile?

    Kevin O’Leary will be replaced.

    1. “What’s a little bigotry, boorishness, and belligerent ignorance there’s some deregulation (even with tariffs) and white-bread entertainment under that pile?”

      When you show up, we get a heaping helping of bigotry plus a healthy dose of stupidity, asshole.

      1. Open wider, clinger. Your betters are not through with you. Your obsequious compliance is appreciated. In fact, you can mutter bitterly and rant all you want.

        1. Open wider, asshole bigot. The electorate is going to jam Trump down your throat one more time.
          Fuck off.

        2. You’re a clown. A buffoon. A tiresome, rancid, smug illiberal progressive with a piece of corn wedged inside your tiny, insignificant brain and it can’t be removed.

        3. Artie! Long time, no see! Were your handlers updating your software?

    2. He will be assimilated. We are the Borg!

  4. You interview Kevin O’ Leary and not Jordan Peterson?

    /stern look of disapproval.

    And I hate those stupid shows Shark Tank and Dragon’s Den.

    /waves fist.

    1. It doesn’t bother me that they won’t interview Peterson, it bothers me that in a time when young men need guidance and to find meaning in life, Nick has the gall to throw shade on the person who is most effective in helping.

      Nick loves illegal immigrants but fuck those white boys.

  5. “I got my first paycheck and I saw something called tax on it.”

    If you are worried about paying taxes, insist on getting paid in cash, or even bitcoin. There is more anonymity. A paycheck is something government goons have no trouble tracing.

    1. You bet! Just tell your employer it’s cash or they can pound sand!
      So it’s bullshit this evening? Sophistry was too difficult?

    2. “If you are worried about paying taxes, insist on getting paid in cash, or even bitcoin”

      Amd your employer will insist on you finding a new job if you keep insisting on that.

  6. Since when is Donald Trump against free speech?

    1. He said he wants stricter libel laws but hasnt acted on it so he is worse for free speech than anti CU liberals who want to change the 1a.

  7. Trump is not a racist, very disappointed with the blatant biased shown by the reporter.

    1. Remember. Reason is trying to appeal to a ‘broader audience’.

    2. Trump seems to be about as racist as most people his age. I’ve found that as people age, especially men, they become less tolerant of changing social norms. Trump is a product of a bygone age and as such has defaulted to the social conservative default that we see in many older people.

      1. It seems like Trump is a ‘racist’ because he made either accurate or slightly hyperbolic statements about Baltimore and related it to a black Congressman who had been talking shit about Trump. Will only old people recognize Baltimore is a complete disaster, dump, shithole, whatever you want to call it? The entire show, the Wire, is basically looked how f’ed up Baltimore is and how hopeless it is. Yet, David Simon calls Trump the racist.

        Apparently, these new rules means that if you are white say anything critical of any black person, for example, Lebron James or Antonio Brown, you too, are a racist.

        That’s an idiotic standard.

        1. “Apparently, these new rules means that if you are white say anything critical of any black person”

          Or any “person of color.” Or any woman. Or anyone transitioning.

          “White man bad” is all you need to remember

        2. Welcome to what happens when there is redistribution from those who do the work that creates the wealth to those who live in a low-intelligence area infested with rattlesnakes and inbred kids like Kentucky’s 5th District – but racists like Demented and Deluded Donald already knew that.

          “. . . Cities like Baltimore, Atlanta and Chicago—where people of every economic stratum live and work—disproportionately fuel the federal tax base, paying more than they receive in services. Meanwhile, rural regions of the country—predominantly white and conservative—consistently draw more in federal support than they contribute—especially when it comes to public entitlements. Federal investment in people and communities, it seems, is only eschewed when it comes to funding the revitalization of non-white communities. . .”
          What separates the racists from the non-racists is that the non-racists admit that the Moocher/Taker Red States being subsidized by the Contributor/Maker Blue States is responsible for the Contributor/Maker Blue States not being able to take care of their own instead of attacking “Those People” for the institutionalized racism that kept them from accessing the government subsides that created the White middle class.

          The racist conveniently pretend to forget that we have the taped deathbed confession (after he found out that he was dying) from the architect of the Reagan Revolution:

          “You start out in 1954 by saying, “Ni@@er, ni@@er, ni@@er.” By 1968 you can’t say “ni@@er” – that hurts you. Backfires. So you say stuff like forced busing, states’ rights and all that stuff. You’re getting so abstract now [that] you’re talking about cutting taxes, and all these things you’re talking about are totally economic things and a byproduct of them is [that] blacks get hurt worse than whites. . . . You follow me – because obviously sitting around saying, “We want to cut this,” is much more abstract than even the busing thing, and a hell of a lot more abstract than “Ni@@er, ni@@er.”

          We have known for decades, even before all the evidence came in that proved trickle-down/supply side Satanomics, aka Conmanitalism, is nothing but a jihad against shared prosperity by the economic terrorists who hate us for the freedoms that strong unions, high marginal tax rates on the parasite class, and proper financial regulations gave us in the late 30s, the 40s, the 50s, the 60s, and the early 70s until the economic terrorists used the economic upheaval caused by the oil embargos to launch their jihad against the middle class and shared prosperity, that “cutting taxes” and/or “tax cuts” was nothing more, or less, than Conservatives repeatedly yelling out the N-Word.

          1. LOL

            So much crazy!

            Look up the demographics in those southern states… All the highest recipients of welfare are the poor BLACK people in the south. Whites in the south use dick all of welfare, just like they do everywhere else.

            Retard can’t even make sure stats he uses to try to support a retarded leftist point actually support his argument…

      2. Ah.

        You’ve found ergo it must be true.

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  9. That fatuous blowhard got rich by selling his books-cooked dot-com to Mattel, which subsequently took a multi-billion-dollar writedown.
    I guess it’s no surprise he thinks Chump is a ”success.”

    1. That’s a rather hyperbolic opinion. Are you some kind of pseudonymous internet poster?

  10. The term “racist” has lost almost all meaning. Nick, I’m sure you’ll get reinvited onto Real Time, so please stop pandering.

  11. Oh, so a single hoi polloi breadwinner can again buy a house (or make the rent without breaking a sweat), pay all the bills on time, raise a family, buy a new car every few years, and still have money left over to hide from the parasite class in a “Socialist” creation called “a savings account.”

    That, and also good to know that those single breadwinners in the working class can also now afford, on top of the above list, to “pay federal income tax” thus eliminating the need for the federal government to run a deficit in order to fund the maintenance of “Western Civilization.”

  12. I’m glad there’s still reputable people willing to show up and smack down your “racist this, racist that” schtick.

  13. 11:23 he is not worried of capitalist survival cause people will KEEP THE GUNS!
    otherwise good bye america and capitalist as you know it!

  14. LOL

    So much crazy!

    Look up the demographics in those southern states… All the highest recipients of welfare are the poor BLACK people in the south. Whites in the south use dick all of welfare, just like they do everywhere else.

    Retard can’t even make sure stats he uses to try to support a retarded leftist point actually support his argument…9xmovies

  15. The moderator is HORRIBLE… pretty obvious he detests Trump. Saying Trump is “anti free trade” is misleading at best, Trump is FAIR trade, you want to do free trade, so will Trump. The current system is set up to have the USA fund the world, Trump is changing that.
    Don’t like it? Tough.

    1. Why is the debt a problem? This guy is an idiot!!!!!!

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