Kevin’s brother is Shane O’Leary, a popular professional rugby union player, who represents Canada at the international level.
After his father’s death, his mother ran the business as an executive, and later married Egyptian economist George Kanawaty, who worked with the United Nation’s International Labour Organization.
The international assignments of O’Leary’s stepfather caused the family to move frequently and live in many places while Kevin was growing up, including in Cambodia, Tunisia, and Cyprus.
Kevin O’Leary had originally aspired to become a photographer, but later developed an interest in business and investment.
After receiving in 1977 an honors bachelor’s degree in Environmental Studies and Psychology, from the University of Waterloo in Ontario, he went on to continue his graduate studies.
He completed his MBA in Entrepreneurship from the Ivey Business School at the University of Western Ontario in 1980.
In 1979, between the first and second years of his MBA program, O’Leary was selected for an internship at Nabisco, an American manufacturer of cookies and snacks headquartered in East Hanover, New Jersey with branches in downtown Toronto.
He then worked as an Assistant Brand Manager for Nabisco’s cat food brand. O’Leary credits his later success in multiple business indeavors to the skills he developed in marketing during his days at Nabisco, crediting the company for giving him the skills he needed at an early age.
After leaving Nabisco, O’Leary began a brief career as a television producer. With two of his former MBA classmates, O’Leary co-founded Special Event Television (SET), an independent television production company that produced original sports programmings such as The Original Six, Don Cherry’s Grapevine with Bobby Orr, and the Hockey Legends.
The company achieved limited success with minor television shows, soccer films, sports documentaries, and short in-between-period commercials for local professional hockey games.
O’Leary has come a long way since his days at Nabisco, currently a world-renown businessman, author, and television personality.
He has since co-founded O’Leary Funds and SoftKey, which is a publisher and distributor of CD-ROM personal computer software for Windows and Macintosh, during the late 1980s and 1990s. It later changed its name to The Learning Company.
Between 2004 to 2014, he appeared on various Canadian television shows, including the business news programs SqueezePlay and The Lang and O’Leary Exchange, as well as the reality television shows Dragons’ Den and Redemption Inc.
More popularly, he is known for his appearance on Discovery Channel’s Project Earth in 2008, as well as his appearance on the popular American show Shark Tank since 2009, a business reality television series on ABC.
Following Stephen Harper’s resignation as leader of the Conservative Party of Canada, O’Leary attended Conservative party gatherings in February and May 2016, leading to public speculation about whether he would run for the 2017 leadership election.
In 2017, O’Leary campaigned to be the leader of the Conservative Party of Canada. He was a frontrunner in the polls during much of that time, but dropped out in April 2017, one month before the election, citing a lack of support in Quebec.
Interestingly enough, throughout his run for the leadership of the Conservative Party of Canada, O’Leary was heavily compared by the media to U.S. President Donald Trump.
The media alleged that both were wealthy businessmen who have gained greater fame as a result of appearing on reality television prior to running for office, on a platform that included lowering taxes and regulations.