Kevin O’Leary Up Close and In Person

Kevin O'Leary and Stacey Robinsmith
Kevin O'Leary and Stacey Robinsmith

As I said yesterday, I went to the Vancouver Convention Centre to see, or perhaps more importantly, to listen to Kevin O’Leary of The Dragon’s Den fame. Entertaining yes, informative yes disconcerting definitely yes.

I have to be up front about things, Kevin O’Leary and I have profoundly different politics. He described himself as politically being a little further right of Attila the Hun.

One of the other things that he said time and again was how he looked forward to being able to fire people. He said when he is making a deal on The Dragon’s Den he will often insist on a 51% share so that when he needs to fire the person who brought the idea to him, he can. Firing people was a recurring theme in his afternoon chat.

He said he would vote for a goat in the federal election if that goat said he was going to significantly reduce the size of our government. He is not a fan of government. In fact he sees government and government regulations as a drain on society.

When it comes to investing he says that he would far rather invest in a call-centre in a country like Cambodia where the young people there will happily work 20 hours a day and sleep under their desks for the other four hours a day just to make 20% more than the person seated near them. He says that he has no desire to invest in the fat lazy teenagers in Canada because they do not want to work as hard as the Cambodian kids.

When it comes to investing his advice was to NEVER invest more than 5% of your portfolio in any one company and to never invest more than 20% of your portfolio in one sector. And do not fall in love with commodities. He also said that he only ever invests in companies who pay dividends because the vast amount of wealth he has earned has been through dividends, not through capital growth of a company.

Another key aspect of his investment philosophy is that debt is EVIL. He says that debt will KILL you. The way he said it made me believe that he feels strongly about the evilness of debt.

When it comes to employees he says his favourite kind of employees are the kind who wake up in the morning and wonder who they are going to pour boiling oil on in order to make more money for him. One employee once said to him, “Kevin, you really are a bastard and I love that about you.” O’Leary said that was a great complement to him.

Although he has a wife and kids, he says that the only thing that matters in life is money. How much money he has in his bank account is the only thing that really matters. In fact he said that when you are old and crusty and dabbling your toes in the lake, nobody other than your money is really going to love you.

Near the end of the session with Kevin O’Leary he said that his guiding philosophy is that he goes to bed every night richer than when he woke up. That is how he sees success.

Although I did learn a few things about investing and how to be successful entrepreneur; he says that a true entrepreneur is one who loves his business more than he loves his girlfriend. Interestingly, he did say girlfriend and not wife. Not sure if that was intentional. Perhaps it is okay to love your wife more than your business and your business is next in line after your business.

I have to admit that I felt more sad at the end of his discussion than informed. Sad because his definition of success seems like such a hollow and empty life. Financially successful but emotionally empty.


  1. He loves money more than sex. Damn. If I fund that I am not going to have another erection…I would kill myself.

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