History of Kevin O'Leary in Timeline
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*.
1 hour ago : Kevin O'Leary's Unconventional Oscars Look: A Card Featuring NBA Legends
Kevin O'Leary attended the 98th Academy Awards wearing a card featuring Michael Jordan, Kobe Bryant, and LeBron James. His red carpet appearance stunned and sparked conversations, drawing attention from prestige filmmakers and the public.
1933: Securities Act Extends to Targeted Solicitation Using Social Media
In 1933, the Securities Act of 1933 extends to targeted solicitation using social media
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.
1993: Softkey's Consolidation in Educational Software Market
By 1993, Softkey had become a major consolidator in the educational software market, acquiring rivals such as WordStar and Spinnaker Software.
1995: Softkey Acquires The Learning Company
In 1995, Softkey acquired The Learning Company (TLC) for $606 million, adopted its name, and moved its headquarters to Cambridge, Massachusetts.
June 1998: The Learning Company Buys Broderbund
In June 1998, The Learning Company (TLC) bought its former rival Broderbund for $416 million.
1999: Acquisition by Mattel and Subsequent Termination
In 1999, Mattel acquired The Learning Company (formerly SoftKey), resulting in significant losses. Kevin O'Leary was subsequently fired by Mattel. The sale netted O'Leary around six million dollars, but also led to shareholder lawsuits.
1999: Mattel Acquires TLC; O'Leary Fired
In 1999, The Learning Company (TLC) was acquired by Mattel for US$4.2 billion. Following the acquisition, sales and earnings for Mattel soon dropped, and O'Leary was fired. Mattel's shareholders later filed a class-action lawsuit accusing Mattel executives, O'Leary, and former TLC CEO Michael Perik of misleading investors.
2003: Co-investment in StorageNow Holdings
In 2003, Kevin O'Leary became a co-investor and corporate director at StorageNow Holdings, a Canadian developer of climate-controlled storage facilities controlled by Reza and Asif Satchu.
2003: Settlement of Shareholder Lawsuit
In 2003, Mattel paid $122 million to settle a class-action lawsuit filed by its shareholders, who accused Mattel executives, Kevin O'Leary, and former TLC CEO Michael Perik of misleading investors about the health of The Learning Company and the benefits of its acquisition. O'Leary disputed all charges.
2004: Appearance on Canadian Television Shows
In 2004, Kevin O'Leary began appearing on various Canadian television shows, including The Lang and O'Leary Exchange and Dragons' Den.
May 2005: Wrongful Dismissal Lawsuit Filed
In May 2005, Reza Satchu and Wheeler, Kevin O'Leary's operating partner, filed a $10-million wrongful dismissal lawsuit, charging that they had altered an agreed-upon compensation deal and illegally reduced Wheeler's share of the profits. The case was later settled out of court.
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.
2006: Self-reference as "Mr. Wonderful"
In 2006, Kevin O'Leary referred to himself as "Mr. Wonderful" in a casting video for Dragon's Den, a name that would later become his popular nickname.
March 2007: Joined Advisory Board of Genstar Capital
In March 2007, Kevin O'Leary joined the advisory board of Genstar Capital, a private equity firm, to seek new investment opportunities for its $1.2 billion fund.
March 2007: Acquisition of StorageNow Holdings
In March 2007, StorageNow Holdings was acquired by Storage REIT for $110 million, resulting in a windfall profit exceeding $4.5 million for Kevin O'Leary.
2008: Co-founded 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 is the company's chairman and lead investor, while his brother, Shane O'Leary, serves as a director.
2008: Co-hosting Discovery Project Earth
In 2008, Kevin O'Leary worked as a co-host for the Discovery Channel's Discovery Project Earth, a show focused on innovative solutions to reverse climate change.
2009: The Lang and O'Leary Exchange Debut
In 2009, Kevin O'Leary began co-hosting The Lang and O'Leary Exchange on CBC News Network with journalist Amanda Lang.
2009: Hosting Winnipeg Comedy Festival gala
In 2009, Kevin O'Leary hosted a Winnipeg Comedy Festival gala called Savings & Groans where he did a Dragon's Den style sketch.
2010: Savings & Groans show aired on CBC
In 2010, the Winnipeg Comedy Festival gala Savings & Groans, which Kevin O'Leary hosted, aired on CBC.
2011: Controversy on The Lang & O'Leary Exchange
During a 2011 segment on The Lang & O'Leary Exchange, Kevin O'Leary criticized journalist Chris Hedges, leading to Hedges' refusal to appear on the show again and a CBC ombudsman finding O'Leary's behavior a violation of journalistic standards.
2011: Separation from Linda Greer
In 2011, Kevin O'Leary and his wife, Linda, separated, although they later resumed their marriage after two years.
2011: O'Leary Funds Manages $400 Million
In 2011, O'Leary Funds' assets under management grew to $400 million.
2012: Co-producing Redemption Inc.
In 2012, Kevin O'Leary co-produced and hosted the reality show Redemption Inc. on CBC, where ex-convicts competed for funding.
2012: O'Leary Funds Manages $1.2 Billion
In 2012, O'Leary Funds' assets under management grew to $1.2 billion.
January 2014: Remark on The Lang and O'Leary Exchange
In January 2014, Kevin O'Leary made a remark on The Lang and O'Leary Exchange.
April 2014: Closure of O'Leary Mortgages
In April 2014, O'Leary Mortgages closed.
September 1, 2014: Joins Discovery Channel and CTV
On September 1, 2014, Kevin O'Leary returned to the Discovery Channel as a contributor for its radio and television stations such as CTV, after having been a co-host of SqueezePlay on Bell Media's Business News Network (BNN).
November 2014: Penalties for Securities Act Violations
In November 2014, O'Leary Funds Management agreed to pay penalties to the Autorité des marchés financiers for violating certain technical provisions of the Securities Act.
2014: Departure from Canadian Television Shows
In 2014, Kevin O'Leary ceased appearing on the Canadian television shows Dragons' Den and The Lang and O'Leary Exchange.
May 5, 2015: Appearance on Celebrity Jeopardy
On May 5, 2015, Kevin O'Leary appeared on Celebrity Jeopardy and won $10,000 for charity, despite finishing 3rd with negative points.
July 14, 2015: Launch of Exchange-Traded Fund (ETF)
On July 14, 2015, Kevin O'Leary launched an Exchange-Traded Fund (ETF) through O'Shares Investments, a division of his investment fund, O'Leary Funds Management LP.
October 15, 2015: O'Leary Funds Sold to Canoe Financial
On October 15, 2015, O'Leary Funds was sold to Canoe Financial, a private investment-management company owned by W. Brett Wilson.
January 2016: Offer to invest in Alberta's economy
In January 2016, Kevin O'Leary offered to invest $1 million in Alberta's economy in exchange for Premier Rachel Notley's resignation.
February 2016: Criticism from Maxime Bernier
In February 2016, Conservative politician Maxime Bernier criticized Kevin O'Leary for wanting to be prime minister without speaking French, leading O'Leary to commit to learning French.
February 2016: Presentation at Conservative conference
In late February 2016, Kevin O'Leary appeared with other prospective leadership candidates at a conference for federal Conservatives, giving a presentation titled "If I Run, This is How."
May 2016: Attending Conservative Party gatherings
In May 2016, Kevin O'Leary attended Conservative Party gatherings, leading to speculation about a potential run for the 2017 leadership election.
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.
January 18, 2017: Enters Conservative leadership race
On January 18, 2017, Kevin O'Leary officially entered the Conservative leadership race, receiving both criticism and endorsement from former Dragons' Den co-stars.
February 1, 2017: Controversy over gun range video
On February 1, 2017, Kevin O'Leary posted a video of himself shooting at a Miami gun range, which was removed from Facebook and drew criticism due to its timing coinciding with the funeral for victims of the Quebec City mosque shooting. O'Leary later apologized.
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.
April 26, 2017: Drops 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 endorsing Maxime Bernier.
2017: Speculation about leadership election run
Following Stephen Harper's resignation, Kevin O'Leary's attendance at Conservative Party gatherings in 2016 led to speculation about whether he would run for the 2017 leadership election.
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".
November 2018: Lawsuit against Elections Canada
In November 2018, Kevin O'Leary sued Elections Canada and Canada's federal elections commissioner over campaign finance laws, arguing they limited candidates' spending and discouraged wealthy individuals from running.
2018: Hosting "Ask Mr. Wonderful" podcast
In 2018, Kevin O'Leary hosted the podcast Ask Mr. Wonderful for seven episodes.
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.
2019: Reason for dropping out of leadership race
In 2017, Kevin O'Leary stated that a reason he dropped out of the Conservative leadership race was because a lack of support in Quebec meant that it would be difficult for him to beat Trudeau in 2019.
2019: Posting "Ask Mr. Wonderful" videos on YouTube
In 2019, Kevin O'Leary began posting videos on YouTube under the title "Ask Mr. Wonderful".
2019: Skepticism Towards Cryptocurrency
In 2019, Kevin O'Leary initially expressed skepticism about cryptocurrency, describing bitcoin as "a digital game" and "useless currency".
May 2021: Allocation to Bitcoin and Investment in Defi Ventures
In May 2021, Kevin O'Leary said he had made a 3 to 5% allocation to bitcoin and had become a strategic investor in the Vancouver-based decentralized finance platform Defi Ventures, which was then renamed WonderFi Technologies.
August 2021: Ownership Stake in FTX and Spokesperson Role
In August 2021, it was announced that Kevin O'Leary would take an ownership stake in the parent companies of FTX.com and FTX.US as part of his compensation for becoming a "spokesperson and ambassador" for FTX.
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.
February 2022: Securities Act Ruling on Social Media Solicitations
In February 2022, the U.S. 11th Circuit Court of Appeals ruled in a lawsuit against Bitconnect that the Securities Act of 1933 extends to targeted solicitation using social media, setting a precedent relevant to individuals promoting fraudulent cryptocurrency ventures.
November 2022: Class-Action Lawsuit Against O'Leary for FTX Promotion
In November 2022, Kevin O'Leary, along with other spokespeople for FTX, was sued in a class-action lawsuit following FTX's bankruptcy due to CEO Sam Bankman-Fried secretly using client funds. O'Leary claimed he lost $9.7 million in digital assets and a further million dollars' worth of equity after the company's insolvency.
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.
2025: Acting debut in Marty Supreme
In 2025, Kevin O'Leary made his acting debut in the movie Marty Supreme, playing Milton Rockwell.
2025: Feature Film Debut
In 2025, Kevin O'Leary made his feature film debut as Milton Rockwell in Josh Safdie's Marty Supreme.
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