The other side of Kevin O’Leary

I had wanted to interview Kevin O’Leary ever since I attended a small presentation on his O’Leary family of mutual funds that he gave to money managers in Vancouver last spring. Before those financial gatekeepers, O’Leary was his usual fast talking self, but more humble and incisive than he appears on TV.

When we were able to sit down and talk in Whistler last Friday, I thought Cambridge House investors should see that side of him. Our discussion revealed a quieter, analytical, and generous side that most people never see. O’Leary articulated his investing philosophy, which also guides his fund family.

It will surprise you: He’s actually very conservative, and believes “an investment without a dividend is simply speculation.” Hence the mandate for capital preservation and income of O’Leary Funds, which are aimed at retail investors.

For an hour, we talked about investing, macroeconomics, geopolitics, life and even wine. So dust off a bottle (1990 Cheval Blanc, Mr. Wonderful’s favorite) and get to know the other side of Kevin O’Leary.

Thanks to Business Insider, Stock SageWall Street Journal and all my Twitter pals for mentioning this interview.

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5 Responses to The other side of Kevin O’Leary

  1. Pingback: An Interview With one of Canada’s Most Successful Investors | The Stock Sage

  2. Great interview, Tommy. You’re a natural at this…or at least it looks it, I’m sure there’s plenty of work that goes into these.

    You didn’t call him on his hammering the ‘guys my age want…’ angle, though. He’s got about as much in common with ‘guys his age’ as I do with Mark Zuckerberg.

    • Zaffar says:

      Thanks for the very nice comments guys. This will be wkleey and I’m sure parts of it will make it onto the air, but I’m not sure it will be aired in its entirety. I kept things pretty broad this week in terms of questions but I’m sure as soon as we see the team play in some games things will get more specific. If you have anything you think I should ask please send along an e-mail (Marc -at- or send me a tweet @Marc_Bertrand.

  3. Pingback: An Interview With one of Canada’s Most Successful Investors | FavStocks

  4. James Deck says:

    Thanks for sharing Tommy. A great interview an astute investor. I personally share a lot of his views (now if only I shared his success).

    It’s funny… listed companies are so about the stock price and the dividend is just a blip on the radar.

    Love his views on the inefficiency of government.

    Favorite quote: “I want to go to bed every night richer than when I woke up”

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