NET WORTH: $300 million
SOURCE of WEALTH: SoftKey, The Learning Company
FUNDING AREAS: Entrepreneurship
OVERVIEW: O’Leary has lent his support to causes such as education and climate change, but his work has been almost entirely about what he can do through capitalism and entrepreneurship, which he believes has more power to do good than giving his money to non-profits. According to Nuvo Magazine, O’Leary and wife, Linda, choose seven charities to focus on for five-year periods, but it’s virtually impossible to find records of his giving.
BACKGROUND: O’Leary grew up in Montreal, and attended the University of Waterloo, followed by the Richard Ivey School of Business at the University of Western Ontario. After co-founding a small television production company and then selling his share for $25,000, O’Leary famously co-founded SoftKey with $10,000 in seed capital from his mother. By the mid 90’s, SoftKey had become a major player in the educational software market, and eventually acquired rivals The Learning Company for $606 million, and later Broderbund for $416 million before being sold to Mattel for $3.8 billion in stock. In 2003, O’Leary began diversifying, becoming a co-investor and director in Storage Now, and then joining the board of the private equity firm Genstar Capital. More recently he’s joined the cast of Canadian hit TV show Dragon’s Den, and the American show Shark Tank, investing in startup businesses that entrepreneurs bring on the shows. He’s also become an author, and created other businesses such as O’Leary Mortgages, O’Leary books, and O’Leary Fine Wines.
ENTREPRENEURSHIP: O’Leary is a lifelong photographer, and in September 2013 he launched an exhibit displaying some of his best work over the last 40 years. Proceeds from the sales of this photography are being donated to the Future Dragon Fund, which O’Leary created to encourage teenage entrepreneurs. Through the fund, O’Leary has given away $5,000 prizes to promising 11th and 12th graders in Canada. Details can be found here.
O’Leary is also working on a show called Redemption Inc., where he helps ten ex-cons improve their business skills, and gives them a chance to compete for $100,000 of his money to build their own business.
FINANCIAL EDUCATION: The Alitis Investment Counsel donated $5,700 from the proceeds from a talk O'Leary gave to the Victoria Foundation’s Smart and Caring Community Fund.
ENVIRONMENT: O’Leary is an entrepreneur, investor, and co-host for the Discovery Channel’s Discovery Project Earth, which explores innovative ways man could reverse climate change. He also once interviewed a young anti-GMO activist where he explains that people who oppose GMOs should "stop eating" so we could "get rid of them."
LOOKING FORWARD: O'Leary has displayed an interest in issues such as climate change and financial education, but the level of his philanthropy remains to be seen.