Kevin O’Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons

Kevin O'Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons
(Image: courtesy of Bell Media)

Love him or loathe him, Kevin O’Leary knows how to get your attention—and he’ll have lots more of it in his new role as CTV Bell Media’s roving (and raving) capitalist

Kevin O'Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons
(Image: courtesy of Bell Media)

Why the move to CTV? Greater reach. CTV has many media assets, so when I look at how many eyeballs I can reach in a week, it’s difficult to compete with them. My TV work—a hobby gone berserk—gives me an opportunity to talk about the things that matter to me.

Which are? Number one is to support Canadian entrepreneurs. Two is advocating for smaller government. Government is incredibly inefficient, and I don’t like the fact that they’re vilifying business and intervening in our sectors. And lastly, as Canadians, we don’t expose our kids to the issues around money early enough. Children should be educated about the merits and risks of money starting at the age of five.

Did you do that with your own kids? Yes, with varied success. I asked them for a percentage of the money they got on their birthdays and then set up accounts for them in trust. They look at the accounts and understand how ­money’s made. I plan to cut them off once their education is done, which my mother did to me. Otherwise they’ll never launch. I see all kinds of entitled kids from wealthy families now and they’re very screwed up.

How did you square your capitalist philosophy with working for the CBC, a government-funded institution? The CBC is a jewel. It has always had one important mandate—telling ­Canadian stories. Along the way, that mandate got changed and the CBC found itself competing with the private sector. That hasn’t ended well, as we know.

You seem to be trying to nuke the stereo­type of the nice Canadian with your prickly persona. Is that your goal? I’m not trying to change the persona of a country. My whole attitude in talking about business is to take the emotion out of it. I try to say, look, here’s the cold hard truth about a business idea, and if you think I’m being cruel, I don’t care, because it’s more important that you learn the truth and you learn it early.

Is there anything viewers don’t know about you that would surprise them? For example, that you love kittens? Well, I spent a long time trying to make a living as an artist—as a filmmaker, a cameraman and a photographer.

Did you stop because you couldn’t make money, or because you weren’t any good at it? I wanted to be an entrepreneur. I combined the two interests when I was doing my MBA at Ivey. I convinced the professors to let me do a documentary about the program, so I shot the experience for 24 months and it became my thesis. Then I visited all the grads five years later to see where they ended up. For about a decade, Ivey used the film to show potential recruits.

So you parlayed that into a business? I started a company, along with two partners, called Special Event Television. We did work for Hockey Night in Canada, among others. We also created Don Cherry’s Grapevine, out of CHCH in Hamilton. Don taught me a lot about being a TV personality. His core lesson, which I never forgot, was don’t make TV that people won’t watch.

To what do you attribute your entrepreneurial leanings? I was born in Montreal and my dad died when I was young. My mother remarried and my stepfather was an oil executive, so we moved every two years. We lived in Cyprus, Cambodia, Ethiopia, Tunisia, Switzerland, France. That gave me an opportunity to understand how the world works.

Are you now dividing your time between Toronto and the U.S.? I have homes in Boston, Toronto, Muskoka and Switzerland, and I try to balance my time among all of them.

Is the antagonism between you and your fellow Dragons and Sharks just a shtick? It’s real. Imagine being in a room with people for 15 hours a day, 22 days in a row. I don’t care who you are, things are going to get testy.

Are you friends with any of them? I call them all friends. Jim Treliving and I spent a day at the cottage together in August.

What did you do? We’re both connoisseurs of California cabernets, and I have a pretty big selection in my cellar. We drank a lot of cab, talked about our investments, then drank some more cab.

So no waterskiing? I think my water­skiing days have reached their limit.


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