As the son of a travelling international business expert, Kevin O’Leary had the opportunity to live and be educated in Cambodia, Cyprus, Tunisia, Ethiopia, France and Switzerland.
After completing his MBA, O’Leary founded Special Event Television, an independent production company that produced original sports programming such as “The Original Six,” “Don Cherry’s Grapevine” and “Bobby Orr and the Hockey Legends.”
O’Leary founded SoftKey Software Products (later called The Learning Company) in 1986. SoftKey was the first software company to apply the principles of consumer goods marketing to the software industry. SoftKey grew quickly as the price of personal computers declined and millions of American families began to buy software for education and entertainment. SoftKey soon became a catalyst of consolidation in the software industry, raising over $1 billion in financing and completing a series of aggressive acquisitions, including WordStar International, Spinnaker Software, Compton’s New Media, The Learning Company, Creative Wonders, the Minnesota Educational Computer Company, Mindscape and Broderbund. By1998, O’Leary’s company was the undisputed world leader in educational, reference and home productivity software and the world’s second largest consumer software company, with annual sales over $800 million, 2,000 employees and offices in 15 countries. In 1999, Mattel acquired the company for $4.2 billion.
In 2003, O’Leary co-founded Storage Now, a leading developer of climate controlled storage facilities. Through a series of development projects and acquisitions, Storage Now soon had operations in 11 cities, serving such companies as Merck and Pfizer, and was acquired by In Storage REIT in March 2007 for $110 million.
In 2007, O’Leary became a founding investor and Director of Boston-based Stream Global Services Inc., focused on the growing out sourcing business services market.
Today, O’Leary is the Chairman of O’Shares Investments. He is also the founder and Chief Sommelier of O’Leary Fine Wines, an award-winning wine label, as well as a member of Boston’s 107-year old Hamilton Trust. In addition to Shark Tank, O’Leary is a regular contributor on ABC, CNBC and CTV, and a bestselling author of two books: Cold Hard Truth and Men, Women and Money, and Cold Hard Truth on Family, Kids and Money.
O’Leary holds a B.A. in environmental studies and psychology from the University of Waterloo and an MBA from the Richard Ivey School of Business, where he serves as a board member.