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O'Leary in March 2011
9 July 1954 |
Montreal, Quebec, Canada
Early life and education 
Growing up, O'Leary was fond of photography and even took it up as a career for some time during his college career. He found soon after that there was unfortunately no money to be made.
He studied for two years at the Royal Military College Saint-Jean followed by the University of Waterloo, where he received an Honours Bachelors degree in Environmental Studies and Anthropology. In 1980, he earned an MBA from the Richard Ivey School of Business at The University of Western Ontario. He attended St. George's School.
Immediately after college, Kevin O'Leary and a couple of friends launched Special event television (SET) and found limited success producing small television shows and in-between periods commercials and local professional hockey games. Later he was bought out for $25,000 by one of his partners. 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 $3.8 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.
Eventually Mr. O'Leary went on to develop O'Leary funds which handles over 1.5 billion dollars. He is also the founder of O'Leary Mortgages and O'Leary fine wines.
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.
O'Leary serves as foil to Journalist Amanda Lang on The Lang and O'Leary Exchange on CBC News Network. He is a venture capitalist on the Canadian television show Dragons' Den as well as a shark on the United States' version of Dragons' Den, Shark Tank, which airs on ABC. He is referred to as "Mr. Wonderful" and "The Undertaker" by Mark Cuban on the show. In addition he has also hosted his own television show, Redemption Inc.
In October 2010 O'Leary used the term "Indian giver" during a live Lang and O'Leary Exchange. After a complaint from an aboriginal person, Alex Jamieson, and condemnation from the CBC Ombudsman, O'Leary offered an apology for his use of the term.
During a segment on the Occupy Wall Street protests on 6 October 2011 episode of the CBC News Network's The Lang & O'Leary Exchange, O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges for sounding "like a left-wing nutbar." Hedges stated afterwards that "it will be the last time [he appears on the show]" and compared the CBC to Fox News. CBC's ombudsman found O'Leary's behaviour to be a violation of the public broadcaster's journalistic standards. O'Leary later acknowledged that he did make a technical mistake during the interview by calling Hedges "a left-wing nutbar" rather than comparing him to one.
- Cold Hard Truth: On Business, Money & Life. Doubleday Canada. 2011. ISBN 978-0385671743
- Cold Hard Truth on Men, Women & Money. Doubleday Canada. 2012. ISBN 978-0-385-67850-6
- Allemang, John. "Kevin O’Leary: The shark who swims alone". The Globe and Mail. 23 September 2011
- Schlesinger, Joel. "The dragon's pen: Reality TV villain writes about life and money in new autobiography". Winnipeg Free Press. 1 October 2011
- "Obituary". Retrieved 2012-03-24.
- Campbell, Colin. "In conversation: Kevin O’Leary". Maclean's. 5 October 2011
- O'Leary, Kevin. (2012) Cold Hard Truth on Men, Women & Money. Doubleday Canada, page 106
- Dignan, Larry. [O'Leary Kevin, (2011) The Cold Hard Truth On Business, Money, and Life, Anchor Canada, Page 135]. ZDNet. 14 December 1998
- "The Worst Deals of All Time?". Retrieved 2012-02-18.
- "Kevin O'Leary: The shark who swims alone - The Globe and Mail". Retrieved 2012-08-06.
- Doyle, John. "It’s one thing to be offended, another to be disgusted". The Globe and Mail. 10 March 2011
- Szklarski, Cassandra. "O’Leary’s ‘nutbar’ remark breach of policy, CBC ombudsman says." Globe & Mail, 14 October 2011. Retrieved 2012-03-23.
- Official website
- Kevin O'Leary at the Internet Movie Database
- The Lang & O'Leary Exchange
- CBC's Dragon's Den bio
- ABC's Shark Tank bio
- O'Leary Funds Inc.
- Time.com: TV's Shark Tank Guru: In Real Life, No Business Whiz