Career
O'Leary started a software company in the basement of a small Toronto home along with partners John Freeman and Gary Babcock. His mother provided the seed investment of $10,000, which he used to start software publisher SoftKey. Softkey products typically consisted of software intended for home audiences, especially compilation discs containing various freeware or shareware game software packaged in a "jewel-case" CD-ROM. By 1994, Softkey had become a major consolidator in the educational software market, acquiring no less than sixty rivals, such as WordStar and Spinnaker Software. In 1995, Softkey acquired The Learning Company (TLC) for $606 million, moved its headquarters to Boston, and took The Learning Company as its name. TLC bought its former rival Brøderbund in June 1998 for $416 million. In 1999, The Learning Company and its 467 software titles were acquired by Mattel in a $3.2 billion stock swap. Sales and earnings for Mattel soon dropped, and O'Leary departed from Mattel. The purchase by Mattel was later called one of the most disastrous acquisitions in history.
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 O'Leary 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 O'Leary to its Strategic Advisory Board to seek new investment opportunities for its $1.2 billion fund. O’Leary 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. He is a former co-host of SqueezePlay on Business News Network, Canada’s national business television specialty channel. O’Leary is currently working as the entrepreneur/investor co-host for the Discovery Channel’s Discovery Project Earth, a project that explores innovative ways man could reverse climate change.
In September 2011, O'Leary released his book, Cold Hard Truth: On Business, Money & Life, where he shares his secrets, experiences, insights, and lessons on entrepreneurship, business, finance, money and life as well as advice for budding entrepreneurs.
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