Hailed as Canada's business equivalent of Donald Trump, O'Leary is one of Canada's most prominent entrepreneurs, investors, and financial pundits. He is the Co-founder and Chairman of O'Leary Funds and the co-founder of Softkey. He has also previously served as a business journalist on CBC's The Lang and O'Leary Exchange with Amanda Lang and hosted Redemption Inc. He is mostly recognized as a tough "Shark" investor on the ABC reality television series Shark Tank as well as a venture capitalist "Dragon" on CBC's Dragons' Den.
Initially aspiring to become a photographer, O'Leary developed an interest in business and investing at a young age watching his mother invest her weekly paycheck into various stocks and bonds. He attended the University of Waterloo in Ontario, obtaining an Honors bachelor's degree and upon receiving his MBA from the University of Western Ontario he set his sights towards carving his niche as a successful businessman.
O'Leary began his career in the early 1980s as an assistant brand manager for Nabisco Foods where he successfully increased market share for Nabisco's biggest cat food brand. He later went on to co-found Special Event Television, a moderately successful television production company that produced original sports programming such as "The Original Six", "Don Cherry's Grapevine" and "Bobby Orr and the Hockey Legends". In 1986, O'Leary co-founded SoftKey Software Products, a leading technology company that sold software geared towards family education and entertainment. SoftKey became a major force in the global educational software industry, where during the late 1980s and 1990s, it acquired many rival companies such as Compton's New Media, The Learning Company and Broderbund. O'Leary's shrewd business acumen helped propel the company into the world leader in the development of educational, reference, and home productivity software, garnering annual sales of over $800 million, 2,000 employees and subsidiaries in 15 countries. SoftKey later changed its name to The Learning Company and was acquired by The Mattel Toy Company in 1999, with the sale making O'Leary a multi-millionaire in the process.