Kevin O’Leary (Paul Lapid/The Canadian Press)

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Who: Co-founder, Chairman, O'Leary Funds

Kevin O'Leary is known to make a splash, but his entrance into business was decidedly understated. After earning his MBA at the Richard Ivey School of Business in 1980, the "Dragons' Den" villain took a reported $10,000 seed investment from his mother and started SoftKey, a software company whose first office was in the basement of a small Toronto home. But from here, O'Leary's career booms. By 1994, SoftKey had become a major consolidator of educational software. The next year the company acquired The Learning Company, a chief rival, for $606 million, and changed its name to that of its recent acquisition. In 1999, then-president O'Leary spearheaded the sale of The Learning Company to Mattel in a deal valued at $3.8 billion. O'Leary would leave Mattel years later, investing in projects like climate-controlled storage facilities. He went on to become a part of the national consciousness in 2006, as an original cast member on CBC's "Dragons' Den" reality show. Two years later, O'Leary co-founded his eponymous investment firm, O'Leary Funds.

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