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Plane Talk: Kevin O’Leary on Trump, self-esteem and a Conservative leadership run

Click to play video: 'Plane Talk with Kevin O’Leary: On the Tory leadership campaign and Donald Trump' Plane Talk with Kevin O’Leary: On the Tory leadership campaign and Donald Trump
WATCH ABOVE: Kevin O’Leary and Tom Clark take to the skies in Ontario’s cottage country to talk Conservative leadership politics, lying and Donald Trump’s parenting skills – Sep 11, 2016

While many Canadians were sitting on their cottage docks watching the sunset this summer, businessman Kevin O’Leary was making plans.

Granted, he was also doing it on his cottage dock, but O’Leary’s summer hideaway near Parry Sound became a prime destination for any Conservative who was contemplating joining the race to replace Stephen Harper.

A handful of candidates have already declared their intention to do so, and a few others are still mulling it over – O’Leary included. He hasn’t officially said he’ll run, but he’ll need to decide soon. The first debate in November is fast approaching.

READ MORE: Kevin O’Leary to make a decision about Conservative leadership this winter

“There’s nothing more fun than sitting on the dock with your toes in the water and talking Canadian politics,” the former Dragon’s Den star told the West Block’s Tom Clark as the two men flew high above O’Leary’s property.

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O’Leary repeated that the Conservative brand “has to reconstitute itself” to survive, a message that he’s been peddling for months now.

“(The candidates) all understand that,” he said.

“Some of the old hacks in there don’t get it, but the brand is broken. The fact is, if they want to win, if the Conservative party ever wants a majority mandate again, it’s going to have to be a much broader, encompassing platform. And that means change.”

READ MORE: Kevin O’Leary joins Conservative party, takes centre stage at convention

O’Leary said he’ll either push for that change himself as a leadership hopeful, “or I back somebody that I believe has the motivation and the same values I have.”

So far, the declared candidates include Kellie Leitch, Tony Clement, Michael Chong, Maxime Bernier, Deepak Obhrai, Brad Trost, Pierre Lemieux, Adrienne Snow and former House speaker Andrew Scheer. Former cabinet minister Peter MacKay has not yet made his decision.

Some of the candidates O’Leary met this summer were not a good fit for his particular brand of politics, he acknowledged, but “others I’m really intrigued with.”

Clark also asked O’Leary if there’s anything about himself he doesn’t like.

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“I’m basically the (components) of my past. If I changed anything I wouldn’t be who I am. You’ve gotta be confident in who you are.”

As for the ongoing presidential race south of the border, O’Leary knows he draws comparisons to Republican nominee Donald Trump. The two men are, in fact, acquainted.

“I know his kids and I know his family and they’re hard-working. They’re not entitled,” O’Leary said.

“How can a man raise such a great family and be as crazy as people think he is? That’s the disconnect I’ve got.”

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