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 TV personality recognized for his appearances on business-related and reality TV shows. He gained prominence through his roles on Canadian programs like SqueezePlay, The Lang and O'Leary Exchange, Dragons' Den, and Redemption Inc. O'Leary expanded his television presence to the U.S. by joining Shark Tank in 2009, further solidifying his image as a shrewd and sometimes ruthless investor.

Sections (4)

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

July 9, 1954: Kevin O'Leary Born

On July 9, 1954, Terrence Thomas Kevin O'Leary, also known as Mr. Wonderful, was born in Montreal, Canada.

July 1954: Kevin O'Leary's Birth

In July 1954, Kevin O'Leary was born in Montreal to Georgette (née Bookalam), a Lebanese small-business owner and investor, and Terry O'Leary, an Irish salesman. Kevin also has a brother, Shane O'Leary.

1977: Graduation from the University of Waterloo

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

1978: Internship at Nabisco

In 1978, between his first and second years of his MBA program, Kevin O'Leary interned at Nabisco in Downtown Toronto and worked as an assistant brand manager for Nabisco's cat food brand.

1980: MBA from University of Western Ontario

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

1986: Starting Softkey

In 1986, Kevin O'Leary started Softkey in a Toronto basement with John Freeman and Gary Babcock. He also convinced his mother to lend him $10,000 in seed capital to establish SoftKey Software Products.

1990: Marriage to Linda Greer

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

2008: Co-founding O'Leary Funds Inc.

In 2008, Kevin O'Leary co-founded O'Leary Funds Inc., a mutual fund management firm focused on global yield investing. He serves as the company's chairman and lead investor.

January 18, 2017: Entering Conservative leadership race

On January 18, 2017, Kevin O'Leary officially entered the Conservative leadership race in Canada.

April 2017: Drops out of 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, one month before the election.

April 26, 2017: Dropping out of Conservative leadership race

On April 26, 2017, Kevin O'Leary dropped out of the Conservative leadership race, citing a lack of support in Quebec and endorsed Maxime Bernier.

August 24, 2019: Involvement in 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 two fatalities.

May 2021: Investment in Bitcoin and WonderFi Technologies

In May 2021, Kevin O'Leary announced he had allocated 3 to 5% of his portfolio to bitcoin and became a strategic investor in the Vancouver-based decentralized finance platform Defi Ventures, which was subsequently renamed WonderFi Technologies.

September 14, 2021: Linda O'Leary found not guilty in boat crash case

On September 14, 2021, Linda O'Leary was found not guilty of careless operation of a vessel in connection with the 2019 boat crash.

2022: Obtaining UAE citizenship

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

2025: Visiting Trump at Mar-a-Lago

In 2025, amid President Donald Trump's threats to impose tariffs on Canadian goods and annex Canada, Kevin O'Leary visited Trump at his Mar-a-Lago resort and supported making Canada part of the United States.