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 television shows like The Lang and O'Leary Exchange and Dragons' Den (2004-2014). He also hosted Discovery Channel's Project Earth in 2008. Since 2009, O'Leary has been a prominent investor on Shark Tank, the American version of Dragons' Den, and appeared as Milton Rockwell in Marty Supreme(2025).
1933: Securities Act of 1933
In November 2022, Kevin O'Leary along with other FTX spokespeople, were sued and the lawsuit cited that 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.
July 9, 1954: Kevin O'Leary Born
On July 9, 1954, Terrence Thomas Kevin O'Leary was born in Montreal, Canada. He is a Canadian businessman and television personality, also known as Mr. Wonderful.
July 1954: Kevin O'Leary Born
In July 1954, Kevin O'Leary was born in Montreal to Georgette Bookalam and Terry O'Leary. He also has a brother, Shane O'Leary. O'Leary also holds Irish citizenship. O'Leary has dyslexia.
1977: Graduated 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 the first and second years of his MBA program, 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: Graduated 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: Started SoftKey Software Products
In 1986, Kevin O'Leary started SoftKey in a Toronto basement, along with business partners John Freeman and Gary Babcock. He secured funding by using 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 (née Greer).
1993: Softkey Consolidates 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, TLC (The Learning Company) bought its former rival Broderbund for $416 million.
1999: Mattel Acquires The Learning Company and Fires O'Leary
In 1999, Mattel acquired The Learning Company for US$4.2 billion, and O'Leary was subsequently fired. Mattel experienced a loss of US$105 million, leading to a drop in stock value and a shareholder lawsuit accusing O'Leary of misleading investors.
1999: Mattel Acquires The Learning Company
In 1999, Mattel acquired The Learning Company, formerly SoftKey, surprising financial observers. Kevin O'Leary netted around six million dollars from the sale but was promptly fired by Mattel. The acquisition resulted in significant losses for The Learning Company and sparked shareholder lawsuits.
2003: Mattel Settles 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.
2003: Co-investor and Corporate Director at StorageNow Holdings
In 2003, 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.
2004: Appeared on The Lang and O'Leary Exchange and Dragons' Den
In 2004, Kevin O'Leary began appearing on Canadian television shows, including the business news program The Lang and O'Leary Exchange and the reality show Dragons' Den.
May 2005: Wrongful Dismissal Lawsuit Filed Against O'Leary and Satchu
In May 2005, Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit. The case was eventually settled out of court.
2006: Self-reference as "Mr. Wonderful"
In 2006, Kevin O'Leary had already referred to himself as "Mr. Wonderful" in a casting video for Dragon's Den, before either show.
2006: Joined Dragons' Den
In 2006, O'Leary appeared as one of the venture capitalists on the Canadian show Dragons' Den on CBC. He developed a blunt and abrasive persona.
March 2007: Joined Genstar Capital Advisory Board
In March 2007, O'Leary joined the advisory board of Genstar Capital, a private equity firm. He was appointed to seek new investment opportunities for its $1.2 billion fund.
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-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 serves as chairman and lead investor.
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 exploring innovative ways to reverse climate change.
2008: Hosted Project Earth
In 2008, O'Leary hosted Discovery Channel's Project Earth.
2009: The Lang and O'Leary Exchange Debut
In 2009, Kevin O'Leary began appearing with journalist Amanda Lang on CBC News Network's The Lang and O'Leary Exchange.
2009: Host of Savings & Groans
In 2009, Kevin O'Leary hosted a Winnipeg Comedy Festival gala called Savings & Groans, featuring a Dragon's Den style sketch about investing in the wheel.
2010: Savings & Groans Aired
In 2010, the show Savings & Groans, which Kevin O'Leary hosted in 2009, aired on CBC.
2011: O'Leary Funds reach $400 million in assets
By 2011, O'Leary Funds had $400 million in assets under management.
2011: Occupy Wall Street Criticism
During a 2011 segment of The Lang & O'Leary Exchange, Kevin O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges for sounding "like a left-wing nutbar," leading to controversy and a CBC ombudsman finding O'Leary's behavior to be a violation of journalistic standards.
2011: Separation from Linda
In 2011, Kevin O'Leary and his wife, Linda, separated.
2012: O'Leary Funds Reach $1.2 Billion in Assets
By 2012, the assets managed by O'Leary Funds had grown to $1.2 billion.
2012: Co-produced and hosted Redemption Inc.
In 2012, Kevin O'Leary co-produced and hosted the reality show Redemption Inc. on CBC, where ex-convicts competed for funding for their business ideas.
2012: Herjavec Leaves Dragons' Den
In 2012, Robert Herjavec left Dragons' Den. Kevin O'Leary remained on both shows for a while.
2013: O'Leary Reflects on "Mr. Wonderful" Nickname
In a 2013 interview, Kevin O'Leary reflected on the nickname "Mr. Wonderful", implying that he could not remember how he got the nickname. He is often referred to by that name in public.
January 2014: Remark on The Lang and O'Leary Exchange
In January 2014, on The Lang and O'Leary Exchange, Kevin O'Leary made a remark.
April 2014: O'Leary Mortgages Closed
In April 2014, O'Leary Mortgages closed.
September 1, 2014: Returns to Discovery Channel
On September 1, 2014, Kevin O'Leary returned to the Discovery Channel as a contributor for radio and television stations such as CTV, after being a co-host of SqueezePlay on BNN.
November 2014: O'Leary Funds Penalized for Securities Act Violations
In November 2014, O'Leary Funds Management agreed to pay penalties to the Autorité des marchés financiers for violating technical provisions of the Securities Act.
2014: End of Dragons' Den Run
In 2014, Kevin O'Leary stopped appearing on the Canadian television shows, including the business news program The Lang and O'Leary Exchange and the reality show Dragons' Den.
May 5, 2015: Celebrity Jeopardy Appearance
On May 5, 2015, Kevin O'Leary appeared on Celebrity Jeopardy and earned $10,000 for his charity, despite finishing in negative points.
July 14, 2015: O'Leary Launched Exchange-Traded Fund (ETF)
On July 14, 2015, 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
In January 2016, Kevin O'Leary offered to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley.
February 2016: Bernier's Criticism
In February 2016, Maxime Bernier criticized Kevin O'Leary, calling him a "tourist" for wanting to be prime minister without being able to speak French. O'Leary stated that he was taking French lessons.
May 2016: Conservative Party Gatherings
Following Stephen Harper's resignation as leader of the Conservative Party of Canada, Kevin O'Leary attended Conservative Party gatherings in May 2016, leading to speculation about a leadership run.
2016: Statement on Business and Family
In a 2016 interview, Kevin O'Leary stated: "In a successful growing business, it eats your time alive. Then later in life, you can provide for your family things that many others can't have. But because you sacrificed, you're then given the reward of freedom."
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 race to be the leader of the Conservative Party of Canada, citing a lack of support in Quebec, one month before the election.
April 26, 2017: Drops out of 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 Bernier.
2017: Speculation About Leadership Election
Following Stephen Harper's resignation as leader of the Conservative Party of Canada, Kevin O'Leary attended Conservative Party gatherings in 2016, leading to public speculation about whether he would run for the 2017 leadership election.
2017: Russia Stance
In 2017, Kevin O'Leary described Russia as "neither an ally nor a foe" in an interview with the CBC.
2017: "Godzilla versus Bambi" Comment
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: Senators Should Pay Idea
In a 2017 interview with Evan Solomon, Kevin O'Leary suggested that Senators should pay money every year, thus turning "a cost centre to Canada" into "a profit centre."
November 2018: Sues Elections Canada
In November 2018, Kevin O'Leary sued Elections Canada and Canada's federal elections commissioner over campaign finance laws that limited candidates to spending only $25,000 of their own money. At the time of the lawsuit, O'Leary still owed $430,000 to creditors.
2018: Ask Mr. Wonderful Podcast
In 2018 Kevin O'Leary hosted the podcast Ask Mr. Wonderful for seven episodes.
August 24, 2019: 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. O'Leary cooperated with the police investigation.
2019: O'Leary Expresses Skepticism About Cryptocurrency
In 2019, O'Leary initially expressed skepticism about cryptocurrency, describing bitcoin as "a digital game" and "useless currency".
2019: Difficulty Beating Trudeau Mentioned
On April 26, 2017, Kevin O'Leary dropped out of the leadership race, stating a lack of support in Quebec meant that it would be difficult for him to beat Trudeau in 2019.
May 2021: O'Leary Invests in Bitcoin and WonderFi Technologies
In May 2021, O'Leary announced he had allocated 3 to 5% of his portfolio to bitcoin and became a strategic investor in WonderFi Technologies.
August 2021: O'Leary Becomes Spokesperson for FTX
In August 2021, O'Leary announced he would take an ownership stake in the parent companies of FTX as 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 connection to the August 2019 boat crash.
February 2022: U.S. 11th Circuit Court of Appeals Rules on Securities Act
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: O'Leary Sued in Class-Action Lawsuit
In November 2022, 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's misuse of client funds. O'Leary lost $9.7 million in digital assets.
2022: UAE Citizenship
In a 2022 CNBC interview, Kevin O'Leary mentioned that he has obtained a United Arab Emirates citizenship in order to partner with Emiratis on investments.
2024: Criticism of Kamala Harris's plan to increase corporate taxes.
During the U.S. presidential election of 2024, O'Leary criticized Democratic presidential candidate Kamala Harris, citing her plan to increase corporate taxes. He also defended Trump for bank fraud. After Donald Trump won the election, O'Leary said he was very happy with the outcome and that he was "very proud of the work I did" during the campaign.
2025: Visit to Mar-a-Lago
Amid President Donald Trump's threats in 2025 to impose 25% 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.
2025: Feature Film Debut
In 2025, O'Leary made his feature film debut as Milton Rockwell in Josh Safdie's Marty Supreme.
2025: Acting Debut in Marty Supreme
Kevin O'Leary made his acting debut in the 2025 movie Marty Supreme, playing Milton Rockwell.
Mentioned in this timeline
Donald John Trump is an American politician media personality and...
Facebook is a social media and networking service created in...
Kamala Harris is an American politician and attorney She served...
The United States of America is a federal republic located...
CNBC is an American business news channel owned by Versant...
Mar-a-Lago is a resort and National Historic Landmark in Palm...
Trending
Belle Fligelman Winestine - was an American writer and activist known for her involvement in the women's suffrage movement As...
23 minutes ago Executive Order proposed 5-year NCAA athlete limit and transfer restrictions.
1 hour ago Shooting near Pauls Valley High School injures one, suspect detained by sheriff.
1 hour ago Alphonso Davies' Absence: Canada's World Cup Hopes Questioned, Flores Shines Amidst Defensive Concerns.
1 hour ago College Football Transfer Portal Heats Up: Projecting Impactful Transfers for the 2026 Season
1 hour ago Musiala's fitness: Kompany, Nagelsmann coordinate return; Bayern addresses injury concerns.
Popular
Paula White-Cain is a prominent American televangelist and key figure...
William Franklin Graham III commonly known as Franklin Graham is...
XXXTentacion born Jahseh Dwayne Ricardo Onfroy was a controversial yet...
Pam Bondi is an American attorney and politician She served...
Eric Swalwell is an American lawyer and politician currently serving...
Melania Trump a Slovenian-American former model has served as First...