Kevin O’Leary’s success story began in his native Canada, “with a big idea and zero cash.” In 1986, he founded SoftKey Software Products, later to be called The Learning Company, in his Toronto basement. Under O’Leary’s leadership, the company became a giant in its sector before it was acquired for $4.2 billion. In 2000, O’Leary founded O’Leary Ventures, a generalist venture capital investment platform that has since invested in start-ups and early-stage companies across virtually every sector. In 2003, he co-founded Storage Now, a leading developer of climate-controlled storage facilities, which was later acquired for $110 million. His next investment, Stream Global Services, was later acquired for $820 million.
In 2006, O’Leary joined the Canadian cast of Dragon’s Den, the international business reality show and forerunner of the U.S. Shark Tank franchise. His tough critiques and brutal honesty made him a popular judge. In 2009, he was invited to join the founding cast of ABC’s Shark Tank, alongside Mark Cuban, Robert Herjavec, Lori Greiner, Daymond John, and Barbara Corcoran. Shark Tank continues to be one of the most popular television programs of all time, garnering multiple awards and nominations, including four Emmy awards. In 2025, he made his acting debut in the movie Marty Supreme alongside Gwyneth Paltrow and Timothée Chalamet. Reflecting his commitment to “eco-preneurship,” O’Leary also co-hosted The Discovery Channel’s Project Earth series, which explored radical ideas to combat global warming.
O’Leary currently serves as chairman for a portfolio of companies that reflect his guiding principles for business. They include venture capital investment platform O’Leary Ventures; Beanstox, an automated internet-based investment advisory service; and O’Shares Investments, which provides ETFs for long-term wealth management. He is the founder of O’Leary Financial Group, and Chief Sommelier of award-winning O’Leary Fine Wines. Since 2021, O’Leary has also been a strategic investor in WonderFi, now one of the largest regulated crypto asset trading platforms in the world.
A strong believer in financial education and fostering the next generation of entrepreneurs, Kevin O’Leary is the author of a bestselling series of books: Cold Hard Truth; Men, Women and Money; and Family, Kids and Money. He has spoken to future entrepreneurs at Harvard Business School, MIT Sloan, Notre Dame, Waterloo and McGill. Corporate speaking audiences have included Ernst & Young, MassMutual, First Third Bank, Constant Contact, Comcast, Zendesk, Cisco Systems, National Conference of State Legislatures, and ExxonMobil.
O’Leary serves on the investment committee of Boston’s prestigious 200-year-old Hamilton Trust. He is an avid chef, wine lover, world traveler, photographer, electric guitarist, guitar collector, and die-hard New England Patriots fan.
Mr. O’Leary received an honours bachelor’s degree in environmental studies and psychology from the University of Waterloo and an MBA in entrepreneurship from the Ivey Business School at the University of Western Ontario.
