O'Leary's success story starts where most entrepreneurs begin: with a big idea and zero cash. From his basement, he launched SoftKey Software Products. As sales took off, O'Leary moved to headquarters in Cambridge, Mass., and went on an industry consolidating acquisition binge. From 1995 to 1999, he bought almost every one of his software competitors. In 1999, O'Leary sold his company to the Mattel Toy Company for 3.7 billion dollars, one of the largest deals ever done in the consumer software industry

O'Leary then founded his own mutual fund company, O'Leary Funds. O'Leary searches globally for opportunities in fast growing emerging markets and invests in companies that pay rich dividends. When he's not squeezing the market from his office in West Palm Beach, he travels the world looking for new opportunities to deploy his capital.

O'Leary is a founding investor and director of Stream Global, an international business outsourcing company; he is on the investment committee of Boston's prestigious 200-year-old Hamilton Trust; and is the chairman of O'Leary Funds. He also serves on the executive board of The Richard Ivey School of Business.