History of Kevin O'Leary in Timeline
Kevin O'Leary, known as 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 (2004-2014). O'Leary has been a Shark Tank investor since 2009. He hosted Discovery Channel's Project Earth in 2008. In 2025, he made his feature film debut.
July 9, 1954: Kevin O'Leary Born
On July 9, 1954, Terrence Thomas Kevin O'Leary, later known as Mr. Wonderful, was born in Montreal, Canada.
July 1954: Birth of Kevin O'Leary
In July 1954, Kevin O'Leary was born in Montreal to Georgette Bookalam and Terry O'Leary. He has a brother named Shane O'Leary and holds Irish citizenship due to his paternal heritage. O'Leary also has dyslexia.
1977: Received Bachelor's Degree
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, between his first and second years of his MBA program, Kevin O'Leary interned at Nabisco in Downtown Toronto and then worked as an assistant brand manager for Nabisco's cat food brand.
1980: Received MBA
In 1980, Kevin O'Leary received an MBA in entrepreneurship from Ivey Business School at the University of Western Ontario.
1986: Started SoftKey
In 1986, Kevin O'Leary started SoftKey in a Toronto basement with John Freeman and Gary Babcock. He secured funding through the proceeds from selling his SET share and a $10,000 loan from his mother.
1990: Marriage to Linda Greer
In 1990, Kevin O'Leary married Linda Greer. The couple separated in 2011, but they resumed their marriage after two years.
1993: Softkey Acquired Rivals
By 1993, Softkey had become a major consolidator in the educational software market, acquiring rivals such as WordStar and Spinnaker Software.
1995: Softkey Acquired The Learning Company
In 1995, Softkey acquired The Learning Company (TLC) for $606 million, adopting its name, and moved its headquarters to Cambridge, Massachusetts.
June 1998: TLC bought Broderbund
In June 1998, The Learning Company bought its former rival Broderbund for $416 million.
1999: Acquisition by Mattel and Subsequent Firing
In 1999, Mattel acquired The Learning Company (TLC) for US$4.2 billion, leading to sales and earnings drops for Mattel and O'Leary's subsequent firing. Shareholders filed a class-action lawsuit accusing Mattel executives, O'Leary, and former TLC CEO Michael Perik of misleading investors.
1999: SoftKey Acquired by Mattel
In 1999, SoftKey, which later changed its name to The Learning Company (TLC), was acquired by Mattel. O'Leary received around six million dollars from the sale but was promptly fired by Mattel. The acquisition led to significant losses for TLC and shareholder lawsuits alleging mismanagement by O'Leary.
2003: Co-investor at 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.
2003: Settlement of Shareholder Lawsuit
In 2003, Mattel paid $122 million to settle a class-action lawsuit filed by shareholders who accused Mattel executives, O'Leary, and former TLC CEO Michael Perik of misleading investors about the health of TLC and the benefits of its acquisition.
2004: Appeared 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 O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit against O'Leary and Satchu, which was later settled out of court.
2006: Appearance on Dragons' Den
In 2006, Kevin O'Leary began his run on CBC's Dragons' Den, the Canadian version of the international show format. He cultivated a blunt and abrasive persona on the show, which contributed to the program becoming highly successful with around two million viewers per episode.
2006: Refers to himself as "Mr. Wonderful"
In 2006, Kevin O'Leary had already referred to himself as "Mr. Wonderful" in a casting video for Dragon's Den, predating either show.
March 2007: Joined Genstar Capital Advisory Board
In March 2007, O'Leary joined the advisory board of Genstar Capital, a private equity firm.
March 2007: StorageNow Acquired by Storage REIT
In March 2007, StorageNow was acquired by Storage REIT for $110 million, resulting in a profit for O'Leary.
2008: Co-hosts Discovery Project Earth
In 2008, Kevin O'Leary co-hosted Discovery Channel's Discovery Project Earth, a show focused on innovative solutions to reverse climate change.
2008: Co-founded O'Leary Funds Inc.
In 2008, O'Leary co-founded O'Leary Funds Inc., a mutual fund management firm focused on global yield investing, with his brother Shane O'Leary serving as a director.
2009: Begins hosting The Lang and O'Leary Exchange
In 2009, Kevin O'Leary began co-hosting The Lang and O'Leary Exchange on CBC News Network with journalist Amanda Lang.
2009: Hosts Winnipeg Comedy Festival Gala
In 2009, Kevin O'Leary hosted a Winnipeg Comedy Festival gala called Savings & Groans, featuring a Dragon's Den-style sketch. This show aired on CBC in 2010.
2010: Winnipeg Comedy Festival Gala Aired
In 2010, the Winnipeg Comedy Festival gala called Savings & Groans, hosted by Kevin O'Leary, aired on CBC. The show featured a Dragon's Den style sketch.
2011: Criticizes Chris Hedges on The Lang & O'Leary Exchange
During a 2011 segment on The Lang & O'Leary Exchange about the Occupy Wall Street protests, Kevin O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges, leading to controversy and a violation of CBC's journalistic standards.
2011: Separation from Linda Greer
In 2011, Kevin O'Leary separated from his wife Linda Greer, but they later reconciled and resumed their marriage after two years.
2011: O'Leary Funds Management Increases
In 2011, the fund's assets under management grew to $400 million.
2012: Hosts Redemption Inc.
In 2012, Kevin O'Leary co-produced and hosted the reality show Redemption Inc. on CBC, where ex-convicts competed for O'Leary's funding.
2012: Leaves Dragons' Den (Canada)
In 2012, Kevin O'Leary left Dragons' Den on CBC, the Canadian version.
2012: O'Leary Funds Increased Asset Management
In 2012, O'Leary fund increased it's asset under management to $1.2 billion.
2013: Comments on "Mr. Wonderful" Nickname
In a 2013 interview, Kevin O'Leary implied he could not remember how he got the nickname "Mr. Wonderful", which had become associated with his reputation for being mean yet helpful to entrepreneurs.
January 2014: Remarks on The Lang and O'Leary Exchange
In January 2014, Kevin O'Leary made a remark on The Lang and O'Leary Exchange. The exact quote is not present in the available context.
April 2014: O'Leary Mortgages Closed
In April 2014, O'Leary Mortgages closed.
September 1, 2014: Joins Discovery Channel and CTV
On September 1, 2014, Kevin O'Leary joined the Discovery Channel as a contributor for its radio and television stations such as CTV.
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: Leaves Dragons' Den (Canada)
In 2014, Kevin O'Leary left Dragons' Den on CBC, the Canadian version.
2014: Continued Appearances on Canadian Television Shows
Until 2014, Kevin O'Leary continued to appear on Canadian television shows such as 'The Lang and O'Leary Exchange' and 'Dragons' Den'.
May 5, 2015: Appears on Celebrity Jeopardy
On May 5, 2015, Kevin O'Leary participated in Celebrity Jeopardy and won $10,000 for his charity despite finishing 3rd with negative points.
July 14, 2015: Launched Exchange-Traded Fund
On July 14, 2015, Kevin O'Leary launched an Exchange-traded fund (ETF) through O'Shares Investments.
October 15, 2015: O'Leary Funds Sold to Canoe Financial
On October 15, 2015, O'Leary Funds was sold to Canoe Financial, owned by W. Brett Wilson.
January 2016: Offers Alberta Investment for Notley's Resignation
In January 2016, Kevin O'Leary offered to invest $1 million in the economy of Alberta if Premier Rachel Notley resigned.
February 2016: Criticized by Maxime Bernier
In February 2016, Conservative politician Maxime Bernier criticized Kevin O'Leary for wanting to be prime minister without speaking French; O'Leary responded by promising to learn French.
February 2016: Presents at Conservative Conference
In late February 2016, Kevin O'Leary appeared with prospective leadership candidates at a conference for federal Conservatives, giving a presentation titled "If I Run, This is How".
May 2016: Attends Conservative Party Gatherings
Following Stephen Harper's resignation, in May 2016, Kevin O'Leary attended Conservative Party gatherings, fueling speculation about a potential leadership run in 2017.
2016: Remarks on Business Sacrifices
In a 2016 interview, Kevin O'Leary commented on the sacrifices made for a successful business, balancing time with family and providing for them later in life.
January 18, 2017: Enters Conservative Leadership Race
On January 18, 2017, Kevin O'Leary officially entered the Conservative leadership race. Arlene Dickinson criticized him, while W. Brett Wilson endorsed him.
April 2017: Dropped 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.
April 26, 2017: Drops out of Leadership Race and Endorses Bernier
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
Following Stephen Harper's resignation, in 2017, there was public speculation about whether O'Leary would run for the Conservative Party leadership election.
2017: Describes Russia as "neither an ally nor a foe"
In 2017, Kevin O'Leary described Russia as "neither an ally nor a foe" in an interview with the CBC.
2017: "Godzilla versus Bambi" Trade Negotiations
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: Suggests Senators Should Pay Money Annually
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."
November 2018: Sues Elections Canada over Campaign Finance Laws
In November 2018, Kevin O'Leary sued Elections Canada over campaign finance laws, which limited candidates to spending only $25,000 of their own money for their leadership campaign. He argued the law discourages wealthy individuals from running and hurts businesses that had pledged money for his campaign.
2018: Hosts Ask Mr. Wonderful Podcast
In 2018, Kevin O'Leary hosted the podcast Ask Mr. Wonderful for seven episodes.
August 24, 2019: Involved 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 deaths and subsequent charges against Linda O'Leary and the pilot of the other boat.
2019: Expressed Skepticism About Cryptocurrency
In 2019, Kevin O'Leary initially expressed skepticism about cryptocurrency, describing bitcoin as a "digital game" and "useless currency."
2019: Starts YouTube Channel "Ask Mr. Wonderful"
In 2019, Kevin O'Leary started posting videos on YouTube under the title "Ask Mr. Wonderful".
2019: Reason for Dropping Out of Leadership Race
In 2019, Kevin O'Leary stated that the reason he dropped out of the Conservative leadership race in 2017 was due to a lack of support in Quebec and that it would be difficult for him to beat Trudeau.
May 2021: Bitcoin Allocation and WonderFi Investment
In May 2021, Kevin O'Leary allocated 3 to 5% of his portfolio to bitcoin and became a strategic investor in Defi Ventures, which was then renamed WonderFi Technologies.
August 2021: Ownership Stake in FTX and Spokesperson Role
In August 2021, Kevin O'Leary acquired an ownership stake in the parent companies of FTX.com and FTX.US, 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 connection to the fatal boat crash that occurred in August 2019.
February 2022: U.S. 11th Circuit Court of Appeals Ruled in Bitconnect Lawsuit
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.
November 2022: Sued in FTX Class-Action Lawsuit
In November 2022, O'Leary, along with other FTX spokespeople, was sued in a class-action lawsuit following FTX's bankruptcy.
2022: Obtains UAE Citizenship
In a 2022 CNBC interview, Kevin O'Leary mentioned that he has obtained a United Arab Emirates citizenship in order to be able to partner with Emiratis on investments.
2024: Comments on the 2024 U.S. Presidential Election
During the 2024 U.S. presidential election, Kevin O'Leary criticized Kamala Harris for her plan to increase corporate taxes, defended Trump for bank fraud, and expressed happiness and pride in his work after Trump won the election.
2025: Acting Debut in Marty Supreme
In 2025, Kevin O'Leary made his acting debut in the movie Marty Supreme, playing Milton Rockwell, a pen magnate.
2025: Feature Film Debut
In 2025, O'Leary made his feature film debut as Milton Rockwell in Josh Safdie's 'Marty Supreme'.
2025: Visits Trump Amid Trade Threats
In 2025, amid Donald Trump's threats to impose tariffs on Canadian goods and annex Canada, Kevin O'Leary visited Trump at Mar-a-Lago and supported making Canada part of the United States.
May 4, 2026: Box Elder County Approved Stratos Project
On May 4, 2026, Box Elder County officials green-lit the proposal for the Stratos project.
May 12, 2026: O'Leary Accused Nonprofits of Chinese Funding
On May 12, 2026, O'Leary accused two Utah-based nonprofit groups opposing the Stratos project, without evidence, of being funded by the Chinese government.
2026: Announced Joint Venture for Data Center in Utah
In April of 2026, Kevin O'Leary announced a joint venture between O'Leary Digital and Utah's Military Installation Development Authority (MIDA) to construct a large data center campus and energy infrastructure in Box Elder County, Utah, known as the Stratos Project.
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