TOO SUCCESSFUL TO RETIRE

O’Leary is certainly well qualified to judge a start-up’s potential. He has had four entrepreneurial successes of his own, including, most recently, O’Leary Funds Inc., a mutual funds company he launched as the industry was consolidating.

O’Leary, 56, was born in Mont-Royal, QC, and educated in Cambodia, Cyprus, Tunisia, Ethiopia, France and Switzerland, as his stepfather worked with the International Labour Organization. “What I learned, moving every two years, was that there’s a whole big world out there, and Canada is just a small part of it,” he says. “Very little of my money is in Canada today”

Following an undergraduate degree in Environmental Studies at the University of Waterloo, O’Leary pursued his MBA at the Ivey School (where he now sits on the Executive Board). “The value of the degree was in the credentials it gave me for raising funds for my business ventures,” he recalls.

O’Leary’s fi st start-up was in television production. He became a founding partner in Special Event Television, an independent production outf it that produced original sports programming such as “Don Cherry’s Grapevine” and “Bobby Orr and the Hockey Legends.” It was the beginning of an ongoing love affair he has had with television.

Then, in the basement of his small Toronto home, he parlayed $10,000 in seed capital from his mother into Soft Key Software Products, developing software to help students with reading and math. He moved the headquarters to Cambridge, MA and went on an acquisition spree before selling his company in 1999 to Mattel Toy for US$3.7 billion dollars, one of the largest deals to that time in the consumer software industry.

In 2003 O’Leary became co-investor and a director in Storage Now, a leading developer of climate-controlled storage facilities.

Through a series of development projects and acquisitions, it became Canada’s third largest owner/operator of storage services. In early, 2008 he co-founded O’Leary Funds Inc., a mutual fund company focused on global yield investing. He is the company’s chairman and lead investor. The firm has $960-million under management across 11 different publicly traded funds. O’Leary brought to the fund company a lesson he learned from his mother: “She would never spend the principal, just the interest. Everything I own has to pay a dividend,” he insists. “I looked for money managers who would do the same thing. I just want to set the investment style, not pick the stocks.”

Meanwhile, O’Leary also became a TV presence. He was a frequent co-host on Business News Network (BNN), the cable specialty channel owned by CTVglobemedia, and became the entrepreneur/investor co-host for the Discovery Channel’s Discovery Project Earth, a program that explores innovative ways to reverse global warming. But his highest visibility in Canada has come from his roles on Dragons’ Den—where he has appeared in all five seasons -- and the Lang-O’Leary sparring matches. He acknowledges that his TV work has helped build his brand, as well as introduced him to investment gurus and market movers.

O’Leary has an offi ce in Toronto and a cottage – shared with his wife and two children -- in the Muskokas. He’s perpetually on the move, though, seeking out new investment opportunities. He’s increasingly in Europe and Asia, and fi nds the travel “just brutal.” While he says he “has to figure out a way to retire,” he tried that for three years following the sale of his soft ware company and got bored “sitting on every beach known to mankind.”

Besides, he still has a to-do list. One goal is to take O’Leary Funds public over the next two to three years; another is to “keep exploring where TV takes me.”