Rise to Success: Career Highlights of Kevin O'Leary

From career breakthroughs to professional milestones, explore how Kevin O'Leary made an impact.

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

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.

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.

1993: Softkey Acquires Rivals

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: TLC Buys Broderbund

In June 1998, The Learning Company (TLC) bought its former rival Broderbund for $416 million.

1999: Acquisition by Mattel and Termination

In 1999, The Learning Company was acquired by Mattel for US$4.2 billion, but sales and earnings dropped, leading to Kevin O'Leary's termination and a shareholder lawsuit alleging accounting tricks to hide losses and inflate revenues.

1999: Acquisition by Mattel and Subsequent Firing

In 1999, The Learning Company, formerly SoftKey, was acquired by Mattel for US$4.2 billion, making Kevin O'Leary a multimillionaire. However, Mattel soon faced financial difficulties and fired O'Leary, leading to significant losses and shareholder lawsuits.

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.

2003: Settlement of Shareholder Lawsuit

In 2003, Mattel paid $122 million to settle a class-action lawsuit filed by shareholders who accused Mattel executives, Kevin O'Leary, and former TLC CEO Michael Perik of misleading investors about the health of TLC and the benefits of its acquisition.

2004: Appearance on Canadian Television

In 2004, Kevin O'Leary began appearing on Canadian television shows such as SqueezePlay, The Lang and O'Leary Exchange, Dragons' Den, and Redemption Inc.

May 2005: Wrongful Dismissal Lawsuit

In May 2005, Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit, alleging altered compensation and reduced profit share. The case was settled out of court.

2006: Appearance on Dragons' Den

In 2006, Kevin O'Leary appeared on Dragons' Den on CBC, developing a persona as a blunt investor. The show became one of the most-watched in CBC history.

2006: Referencing "Mr. Wonderful" in Dragon's Den casting video

In 2006, Kevin O'Leary had already referred to himself as "Mr. Wonderful" in a casting video for Dragon's Den, predating both Dragon's Den and Shark Tank television shows.

March 2007: Joins Genstar Capital Advisory Board

In March 2007, Kevin O'Leary joined the advisory board of Genstar Capital, a private equity firm. Genstar Capital appointed O'Leary to its Strategic Advisory Board to seek new investment opportunities for its $1.2 billion fund.

March 2007: Acquisition of StorageNow and Profit Realization

In March 2007, StorageNow was acquired by Storage REIT for $110 million, leading to Kevin O'Leary selling his shares and realizing a profit exceeding $4.5 million.

2008: Appearance on Project Earth

In 2008, Kevin O'Leary appeared on Discovery Channel's Project Earth.

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.

2008: Co-hosting 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.

2009: Beginning 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: Hosting Winnipeg Comedy Festival gala

In 2009, Kevin O'Leary hosted a Winnipeg Comedy Festival gala called Savings & Groans, performing a Dragon's Den-style sketch.

2009: Appearance on Shark Tank Begins

In 2009, Kevin O'Leary was invited by Mark Burnett to appear on the American version of Dragons' Den, Shark Tank. Shark Tank became a ratings hit.

2011: O'Leary Funds AUM Growth

In 2011, O'Leary Funds Inc. assets under management grew to $400 million.

2012: Co-producing and hosting 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: O'Leary Funds AUM Growth

In 2012, O'Leary Funds Inc. assets under management grew to $1.2 billion.

2012: Robert Herjavec leaves Dragons' Den

In 2012, Robert Herjavec left Dragons' Den. Kevin O'Leary and Robert Herjavec appeared on both Dragons' Den and Shark Tank for several years.

April 2014: Closure of O'Leary Mortgages

In April 2014, O'Leary Mortgages closed.

September 1, 2014: Joining Discovery Channel and CTV as contributor

On September 1, 2014, Kevin O'Leary became a contributor for Discovery Channel's radio and television stations, including CTV, after having co-hosted SqueezePlay on 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: End of Canadian Television Appearances

In 2014, Kevin O'Leary concluded his appearances on various Canadian television shows, including SqueezePlay, The Lang and O'Leary Exchange, Dragons' Den, and Redemption Inc.

2014: Kevin O'Leary leaves Dragons' Den

In 2014, Kevin O'Leary left Dragons' Den, though he has remained with Shark Tank since its beginning.

July 14, 2015: Launch of O'Shares Investments

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: Sale of O'Leary Funds 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 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.

2018: Hosting Ask Mr. Wonderful podcast

In 2018, Kevin O'Leary hosted the podcast "Ask Mr. Wonderful" for seven episodes.

2019: Skepticism about Cryptocurrency

In 2019, Kevin O'Leary expressed skepticism about cryptocurrency, describing bitcoin as "a digital game" and "useless currency".

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.

August 2021: Partnership with FTX

In August 2021, Kevin O'Leary took an ownership stake in the parent companies of FTX.com and FTX.US to become a spokesperson and ambassador for FTX.

2021: Appearing on CNBC's Money Court

In 2021, Kevin O'Leary appeared on CNBC's Money Court with Katie Phang and Ada Pozo, where they adjudicated financial disputes.

November 2022: Lawsuit Over FTX

In November 2022, Kevin O'Leary was sued in a class-action lawsuit, alongside other FTX spokespeople, after FTX went bankrupt due to CEO Sam Bankman-Fried's misuse of client funds.

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.