He’s opinionated and ruthless, and he hungers for big deals. Yet he made millions helping children learn how to read. Nothing if not a polarizing force, Kevin O’Leary pulls no punches when it comes to the good, the bad, and the ugly as it pertains to markets and economic opportunities. A judge on Shark Tank and a contributor to CTV, as well as the author of the two bestselling books, Cold Hard Truth: On Business, Money & Life and Cold Hard Truth on Men, Women, and Money. O’Leary is also previously well-known as the former co-host of The Lang & O’Leary Exchange and as a former panellist on the wildly popular program, Dragons’ Den.
The New York Times Magazine recently publishes a Q&A with O’Leary. Here are a couple of highlights:
“Shark Tank” airs updates for its successful businesses, but viewers don’t hear about all the businesses that fail. Is there a danger in glamorizing entrepreneurship? No. Even in the updates you see how brutal people’s lives are. Entrepreneurship is a personal sacrifice for a long period of time. I never saw my kids grow up — they just went from zero to teenagers when I was traveling the world selling software, and yet today they enjoy certain freedoms that I could never have afforded had I not been successful.
Many contestants have a sad or inspirational back story. What goes through your head when they start crying during a pitch? Tears buy you nothing. At the end of the day, the market is a brutal place. Nobody cares that you had a little dog when you were in high school that you fell in love with. Nobody gives a [expletive]. You’re now in the real world, competing with people in Mumbai and Shanghai and Hong Kong who want to eat your lunch.
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Last year you were the favorite in the race to become leader of Canada’s Conservative Party, but you dropped out because you felt you couldn’t speak French well enough to win Quebec in a general election. Have you been practicing since then? I have been. I felt that I could bring something to the Canadian market as the prime minister, because Canada’s incredibly mismanaged at a provincial and federal level. Would I do it again? Probably not the same way. Am I glad I did it? Yes.
If you did run again, what would you do differently? I’d be completely bilingual.
What’s the most Canadian thing about you? I’m born from Lebanese and Irish parents. The greatest thing about Canada is that it has allowed anybody to come from anywhere and be accepted in that society. That’s the biggest difference in policy when people say I am like Trump. How can I be Trump? I’m half Lebanese, half Irish. I wouldn’t exist if there were a wall around Canada!
Read the full interview here.