Born to a middle class family in a suburb of Montreal, Kevin's parents divorced when he was young, and his father died shortly after that. His mother re-married George Kanawaty, an executive in the United Nations International Labour Organization. George describes Kevin as an unpredictable teenager. He would often advise him to put down the guitar and pick up a book. Together they spent many sleepless nights discussing Kevin's future. Kevin lived and was educated in Waterloo, Ontario.
It was while working at a Magoo's Ice Cream Parlour, Kevin had a life changing experience. During his second day of work, the store owner demanded he get down on his knees and scrape the gum off the floor. His response was "no," at which point he was instantly fired. Minutes later he was on his way home ashamed and in shock that someone else could have that kind of control over him. The impact of this experience still guides him in his business decisions to date. Since then he has been self-employed.
Kevin started his own software company in the basement of a small Toronto home along with his business partner at the time, Gary Babcock. His mother provided the seed investment of $10,000, which he used to start software publisher SoftKey. His partner Gary left just as numerous mergers and acquisitions allowed the company to become The Learning Company and Kevin took control as president. In 1999, the Learning Company was sold to Mattel for $3.7 billion USD, one of the largest deals ever done in the consumer software industry. Kevin left Mattel in 2000 surrounding a legal dispute over the financial condition of the company at the time of sale.
In 2003 he became co-investor and a director in Storage Now, a developer of climate controlled storage facilities. Through a series of development projects and acquisitions, Storage Now became Canada's third largest owner/operator of storage services with facilities located in eleven cities serving such companies as Merck and Pfizer when it was acquired by the In Storage REIT in March 2007 for $110 million.
In March 2007 Kevin joined the advisory board of Genstar Capital, a private equity firm that focuses on investments in selected segments of life science and healthcare services, industrial technology, business services and software. Genstar Capital appointed Kevin to its Strategic Advisory Board to seek new investment opportunities for its $1.2 billion fund. Kevin also serves on the executive board of The Richard Ivey School of Business at the University of Western Ontario. He is a member of the investment committee of Boston's 107 year old Hamilton Trust and an investor of EnGlobe, a TSX listed company.
In January 2008 he co-founded O'Leary Funds Inc., a mutual fund company focused on global yield investing. He is the company's chairman and lead investor. The firm currently has $960,000,000 under management across 11 different publicly traded funds.
Kevin is also one of Canada's most recognizable television personalities. He is a former co-host of "SqueezePlay" on Business News Network. Currently he's a venture capitalist on CBC Television's "Dragons' Den," the co-host of CBC News Network's "The Lang and O'Leary Exchange," and a "shark" on ABC's "The Shark Tank."
Kevin currently has a luxury cottage on Lake Joseph in Muskoka where he spends his weekends during the summers. He is also a wine enthusiast and enjoys playing guitar.