Kevin O’Leary – entrepreneur, straight shooter and TV personality

He’s extremely successful. He must be. Anyone who can attract investments of $760 million in 30 months is evidently very good at what they do.

An entrepreneur in his own right, he launched SoftKey Software Products on zero cash from his basement, bought out his competitors and sold the then-named Learning Company to Mattel for more than CAD$4 billion in 1999. “Back then, I thought I would be retired by now,” he told us. “I did try retirement for three years, but I was bored. It shocked me to find out how depressed I was when not working on growing a business.”

So, among other ventures, he established O’Leary Funds, of which he is chairman, having ‘fired’ his own fund managers a handful of years ago because he was frustrated with them. During Kevin’s boyhood, his own seamstress mother had ingrained into him a ‘protect your capital’ mantra, and those money managers were not aligned with this philosophy. He decided to take charge.

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“It’s a noble pursuit, creating wealth. I’m a big fan of capitalism, and it should be a cultural phenomenon in Canada.

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TV appearances are, for Kevin, a “fascinating hobby”, with which he has fun, hectic though it is. Broadcast TV also admittedly provides him with unprecedented access to business opportunities, globally. While time consuming, everything he does on TV has to do with his entrepreneurial style and investment philosophy, and he uses the broadcast medium to help build his brand.

Through the TV lens, Montreal-born Kevin may appear ruthless, but remember there is a TV show being made. In reality TV, drama is everything, so a distinct delivery style is encouraged. With a style that, having met him, I’d describe as direct and honest, Kevin is highly opinionated, has an insatiable hunger for big deals and loves to be in control.

“Though some find my style harsh, I just tell the truth all the time. It’s easier.”

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