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Kevin O’Leary on ‘Shark Tank,’ his persona, & politics

Larry King NowSep 26 '16

Do we have Mr. Wonderful all wrong? Kevin O’Leary comes clean about whether his mean-guy persona on ‘Shark Tank’ is an act, why he prefers to invest in women, and if he’s really considering running for Prime Minister of Canada.


Famously ruthless businessman Kevin O'Leary, most known as one of the sharks on the reality competition series 'Shark Tank', sits down with Larry King to talk money, politics, and showbusiness. O'Leary gives the behind-the-scenes scoop on the ABC series, which returned to ABC for its eighth season on September 23--but he also gets deep with his personal financial and political beliefs, including whether he really considers himself Canada's counterpart to Donald Trump.

Ironically labeled "Mr. Wonderful" on the 'Shark Tank' set, the tough judge goes in depth about the hit series, which he has appeared on for each of its eight seasons. O'Leary tells of his skepticism when first pitched the idea for the show, the keys to success he's learned from watching so many entrepreneurs' presentations, and whether his relationship with fellow shark Barbara Corcoran is as contentious as it seems. Plus, he explains why he thinks most of his successful business partnerships have been with women.

But O'Leary goes beyond discussing his life on TV. The multimillionaire has recently publicized his political aspirations--he may run for leadership of Canada's conservative Opposition Party. With this as a starting point, O'Leary reveals his opinion of the 2016 Presidential race, Canada's Prime Minister Justin Trudeau, and what he calls the "political mediocrity" of many members of the US and Canadian governments. 


*Posted Online on Ora.TV on Sept 26th 2016:

"I like to tell the truth on that show and she doesn't. And I fault her for it all the time. When you're in front of an entrepreneur that has an idea with no merit, that you know with certainty is going to go bankrupt, and she doesn't want to hurt their feelings? I call BS on that. You got to tell them the truth." - on her 'Shark Tank' costar Barbara Corcoran

"I thought it was insane. I thought it was a really crazy idea. Because, I remember when I was first talking to Mark Burnett, we were having breakfast at Shutters and I said, 'Wait a minute, Mark. I take my money, and I pay the awards, the prizes, and you own the show?' He said 'You got it, Kevin.' And I said 'That's crazy!'" - on his reaction when first approached about 'Shark Tank'

"I have a saying. If I don't buy your deal or you don't take mine, you're just dead to me. I don't care. I've forgotten who you are before you've even walked out of the tank. You know why? Because there'll be 30 more deals coming at me in the next hour." - on whether he ever regrets not making a deal on the show

"There's an old adage that says 'If you want something done, give it to a busy mother.' It's true in small cap businesses that women are better allocaters of time. Imagine. I've got all of my dough back from women-lead companies. So I'm a huge advocate. I invest in women-based deals because they work." - on how all of his successful 'Shark Tank' deals have been with women

"My theory is this. When you watch Shark Tank, what are you actually seeing? You're seeing the pursuit of freedom. In America, if you can take a product or idea and be successful, that buys your freedom for the rest of your life. And it's very visceral and powerful to see that emotion, that attempt to get the first check, to see if that path can start." - on what makes 'Shark Tank' successful

"There's three elements that are always there in a successful pitch. Number one is they're able to explain the opportunity in 60 seconds or less. A company like Wicked Good Cupcakes: I make a cupcake, I put it in a jar, I FedEx it to you. I get it. Number two, they explain why they're the right team to execute the business plan. And here's the killer, here's the one where I've seen glory plunge to death, I hear the air being sucked out of the room: You gotta know your numbers or you're screwed." - on what makes a successful pitch

"I like to say about politicians who come in on a wave of popularity, it's like that woman you fall in love at the beginning and it's just so euphoric. Couple of years later, how's it going? And that's the problem he's going to have. Because he's not delivering what the country needs. It's the same in the states." - on his opinion of Canadian Prime Minister Justin Trudeau

"And I thought 'Gee, this is interesting.' I've got a huge following. Why don't I start just shining a light at transparency, on these mediocre politicians? Let's call them out. They made promises, they don't deliver. Let me fry them like an ant under a microscope. I'm having so much fun it's ridiculous." - on the beginning of his political ambitions

"I wouldn't make a decision yet. And my kids can vote, and they're always asking. I want to hear more about the economic plan. I care about job creation. That's what I am, I'm an investor. I don't like what I've seen." - on whether or not he would vote for Trump if he were an American citizen

"I actually think what motivates entrepreneurs is fear of failure. And it certainly happened to me. You start a deal, it's not working. You work harder to make it work, you pivot, you figure out what you're doing wrong. Fear of failure is the ultimate motivation and I think every entrepreneur has failures." - on how failure affects entrepreneurs