Childhood and Education Journey of Kevin O'Leary in Timeline

An overview of the childhood and early education of Kevin O'Leary, highlighting the experiences that shaped the journey.

Kevin O'Leary, a.k.a. Mr. Wonderful, is a Canadian businessman and television personality. He gained prominence through appearances on Canadian shows like *The Lang and O'Leary Exchange* and *Dragons' Den*. He hosted Discovery Channel's *Project Earth* and has been a mainstay on *Shark Tank* since 2009. O'Leary also ventured into acting, debuting in the film *Marty Supreme*.

Sections (4)

Full Timeline Early Life & Education Career & Achievements Controversies & Scandals

July 9, 1954: Kevin O'Leary's Birth

On July 9, 1954, Terrence Thomas Kevin O'Leary, also known as Mr. Wonderful, was born. He is a Canadian businessman, television personality, and actor.

July 1954: Kevin O'Leary's birth

In July 1954, Kevin O'Leary was born in Montreal, Canada to Georgette Bookalam and Terry O'Leary. O'Leary has dyslexia which he argued helped him in business by fostering out-of-the-box thinking.

1977: Graduation from the University of Waterloo

In 1977, Kevin O'Leary received an honors bachelor's degree in environmental studies and psychology from the University of Waterloo.

1978: Internship at Nabisco

In 1978, Kevin O'Leary was selected for an internship at Nabisco in Downtown Toronto and then worked as an assistant brand manager for Nabisco's cat food brand.

1980: MBA from Ivey Business School

In 1980, Kevin O'Leary received an MBA in entrepreneurship from Ivey Business School at the University of Western Ontario.

1986: SoftKey Software Products Founding

In 1986, Kevin O'Leary started SoftKey in a Toronto basement with partners John Freeman and Gary Babcock. He secured funding by selling his SET share and borrowing $10,000 from his mother.

1990: Marriage to Linda Greer

In 1990, Kevin O'Leary married Linda Greer, marking the beginning of their relationship.

2006: Appearance on Dragons' Den

In 2006, Kevin O'Leary became one of the five venture capitalists on CBC's Dragons' Den, developing a persona as a blunt investor. This persona was encouraged by the show's executive producer.

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2011: Separation from Linda Greer

In 2011, Kevin O'Leary and his wife, Linda, separated, although they later resumed their marriage after two years.

2016: Statement on balancing business and family

In a 2016 interview, Kevin O'Leary discussed the sacrifices required for business success and the rewards of providing for one's family.

April 2017: Withdrawal from Conservative Party Leadership Race

In April 2017, Kevin O'Leary dropped out of the Conservative Party of Canada leadership race, citing a lack of support in Quebec.

2017: Compares trade negotiations to "Godzilla versus Bambi"

In 2017, Kevin O'Leary described hypothetical trade negotiations between US President Donald Trump and Canadian Prime Minister Justin Trudeau as "Godzilla versus Bambi".

2017: Proposal about Senators

In a 2017 interview with Evan Solomon, Kevin O'Leary suggested that Senators should pay money every year, instead of being paid, thus turning "a cost centre to Canada" into "a profit centre."

2017: Remarks about Russia

In a 2017 interview with the CBC, Kevin O'Leary described Russia as "neither an ally nor a foe".

August 24, 2019: Involvement in a fatal boat crash

On August 24, 2019, Kevin O'Leary and his wife Linda were involved in a fatal boat crash on Lake Joseph in Muskoka, Ontario, resulting in the deaths of two people on the other boat. Linda was allegedly operating the O'Leary's boat at the time.

September 14, 2021: Linda O'Leary found not guilty

On September 14, 2021, Linda O'Leary was found not guilty of careless operation of a vessel in relation to the 2019 fatal boat crash on Lake Joseph.

2022: Obtaining UAE citizenship

In a 2022 CNBC interview, Kevin O'Leary mentioned he obtained a United Arab Emirates citizenship to partner with Emiratis on investments.

2024: Involvement in U.S. presidential election

During the U.S. presidential election of 2024, Kevin O'Leary criticized Kamala Harris' tax plan and defended Donald Trump for bank fraud, later expressing happiness with Trump's victory and pride in his own work during the campaign.

2025: Visiting Trump at Mar-a-Lago and supporting Canada's annexation

Amid Donald Trump's threats to impose tariffs and annex Canada in 2025, Kevin O'Leary visited Trump at Mar-a-Lago, supported making Canada part of the United States, and touted the economic benefits of such a union.