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Will the real Kevin O'Leary please stand up?

Kevin O'Leary plays a particular kind of persona on <i>Shark Tank</i>, but it's not quite who he is in the boardroom. (CNBC/ABC)
Kevin O’Leary plays a particular kind of persona on Shark Tank, but it’s not quite who he is in the boardroom. (CNBC/ABC)

It hasn’t even been a week since Kevin O’Leary announced his Conservative leadership bid and already it looks like the Canadian businessman is working overtime to distance himself from the cartoonish villain millionaire he’s spent the past decade playing on reality television.

Unfortunately for O’Leary, the Internet doesn’t forget. It’s rife with so-called O’Learyisms, countless quips from his stints on both Dragons’ Den and Shark Tank and heated debates on The Lang and O’Leary Exchange.

But as “Mr. Wonderful” recently told The Toronto Star, off-colour comments – like, for instance, those made in 2014 about 3.5 billion people living in poverty “is fantastic” because it inspires them to better their situation ­– were essentially just edgy plays at creating “good television.”

“I explored thousands of ideas, some of them very controversial, some of them very interesting … (but) none of it’s policy,” O’Leary said. “I wasn’t making policy, I wasn’t running as a candidate to govern the country. There’s a difference. People aren’t stupid in Canada, they get it.”

He’s also stood by a lot of what he’s said, according to Duff Conacher, co-founder of Democracy Watch.

“He’s said what he said on TV is what he believes so if he’s trying to deny some of those statements now, other times he’s said those which he expresses as opinions are his views,” he says

So what happens when the media and his fellow candidates take him to task?

“I can only hope that the media looks at any proposal and says we need to know: who, what, where, when, why, and how in detail, because the devil is in the detail of any platform proposal,” adds Conacher. And some of his viewpoints may not mesh well with his peers, let alone voters.

For instance, the Democracy Watch co-founder says that O’Leary has pointed to gaining the support of 18- to 35-year-olds for the party.

“He’s also said that businesses should not have a social conscience which does not align with where most 18- to 35-year-olds are,” says Conacher.

But if the success of a certain reality television star (sworn in as 45th President of the U.S.A. on Friday) south of the border is any indicator, the persona doesn’t necessarily need to be scrubbed clean in order to get your foot in the door (read: lead a country).

“I think (O’Leary) looks to the south and sees that although financially at different levels, a very wealthy businessman with a wicked tongue is now the President of the United States and he’s probably thinking why not me?” Dr. Marie Bountrogianni, dean of the G. Raymond Chang School of Continuing Education and former MPP told Yahoo Canada Finance. “He’s probably thinking he can have the same success (but) the thing is we are two different countries and two different people.”

There’s no doubt his household recognition will help point media attention at him as he and 13 other Conservatives jockey for position in the leadership race, says Bountrogianni. Psychologists call it the mere-exposure effect – “a psychological phenomenon whereby people feel a preference for people or things simply because they are familiar.”

Of course, the added exposure has already put O’Leary – who is worth an estimated US$400 million – and his business record at odds with the tycoon persona he’s crafted for himself on television.

“I did a bit of digging into his financial background myself and like Trump, it’s not clean, it’s controversial,” says Bountrogianni. “When you are running for leader, there are no secrets, people will dig up things in your past that you may have thought were completely forgotten.”

Born in Montreal in 1954, O’Leary clinched his MBA from the University of Western Ontario before launching a television production company that produced shows including some for Don Cherry. At 29, he went on to launch SoftKey Software Products out of his Toronto basement, tapping into the emerging personal computing and software market in the early 1980s before moving the company to Boston. By 1993, SoftKey was trading on the Nasdaq with revenues of $110-million and a loss of $57 million. The company went on an acquisition spree, snapping up The Learning Company. Post-acquisition, SoftKey switched its name to TLC.

But here’s where the businessman and the business-myth start to diverge. In 1998, Mattel made a US$3.8 billion offer for TLC. The purchased proved disastrous with Mattel converting a projected $50-million profit into a loss between $50- and $100-million, within a year of purchasing TLC. O’Leary had been ousted six months after the purchase. Shareholders were unimpressed; filing a class action lawsuit against Mattel (O’Leary was also on the defendants list) alleging TLC had used accounting to hide loses and inflated revenue.

In 2003, O’Leary invested in StorageNow Holdings with entrepreneur Reza Satchu. During this time, O’Leary got his first shot in front of the cameras as “the villainous” venture capitalist on Dragon’s Den. A year after the first episode aired in 2006 Satchu and O’Leary sold StorageNow for $110 million and O’Leary walked away an estimated $4.5 million richer.

With his profile on the rise, O’Leary decided to cash in on his brand and launch O’Leary Funds Management with former Wall Streeter Connor O’Brien. Absent a proper investing license, O’Leary was more of the face of the fund, which gave him space to air his shtick.

Initially, he grew it to an alleged $1.5-billion but by 2015 that had dropped to $800-million (albeit, fund managers have been hurting across the board). There were also mutterings on Bay Street that the company had allegedly been paying out dividends to investors with their very own cash, despite O’Leary insistence that he would not do that.

Ultimately, O’Leary got out of the business, selling it to former Dragons’ Den co-star Brett Wilson (O’Leary had since joined Shark Tank in the U.S.) During that time, in 2012, he also started O’Leary Mortgages but shuttered it less than two years later. All this occurred while he was revolving between Dragons’ Den, Shark Tank and The Lang and O’Leary Exchange.

More recently, O’Leary has been getting into the exchange-traded funds market, launching O’Shares Investments (with O’Brien). According to a breakdown by Bloomberg’s ETF analyst, the use of passive investing strategies (a conservative change of pace for Mr. Wonderful) and an emphasis on “quality” will help him differentiate himself. And of course, his celebrity status hasn’t hurt in the past when it comes to wooing investors.

So maybe O’Leary doesn’t need to divorce himself from his business failures, from his O’Learyisms and bold opinions, maybe he’s exactly who he needs to be in order to get the votes, should he make it through the 13 candidate death match that is the Conservative leadership race.

As O’Leary said it himself, screen-time opens doors: “There’s nothing like television for access to people. It’s like a moth to a candle. It’s a phenomenal platform. That’s why I do it.”