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, also known as Mr. Wonderful, is a Canadian businessman, television personality, and actor. He gained prominence through appearances on Canadian television shows like "The Lang and O'Leary Exchange" and "Dragons' Den" from 2004 to 2014. He is widely known for his role as an investor on the American reality show "Shark Tank" since 2009. O'Leary also hosted Discovery Channel's "Project Earth" in 2008 and made his feature film debut in 2025.

Sections (4)

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

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.

1986: Started SoftKey

In 1986, Kevin O'Leary started SoftKey in a Toronto basement, along with business partners John Freeman and Gary Babcock. He used the proceeds from selling his SET share and a $10,000 loan from his mother to fund the company.

1993: Softkey became a major consolidator

By 1993, Softkey had become a major consolidator in the educational software market, acquiring rivals such as WordStar and Spinnaker Software in the process.

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 (TLC) bought its former rival Broderbund for $416 million.

1999: SoftKey acquired by Mattel

In 1999, SoftKey, which later changed its name to The Learning Company, was acquired by Mattel. Kevin O'Leary, who was the co-founder of SoftKey, was fired by Mattel shortly after the acquisition.

1999: TLC Acquired by Mattel; O'Leary Fired

In 1999, The Learning Company (TLC) was acquired by Mattel for US$4.2 billion, and Kevin O'Leary was subsequently fired. The acquisition was later called one of the most disastrous corporate acquisitions in recent business history. Mattel's shareholders later filed a class-action lawsuit.

2003: Co-investor and corporate director 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.

2004: Appeared on The Lang and O'Leary Exchange

In 2004, Kevin O'Leary began appearing on various Canadian television shows, including the business news program 'The Lang and O'Leary Exchange'.

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2006: Appeared on Dragons' Den

In 2006, Kevin O'Leary appeared as one of the five follow-up venture capitalists on the Canadian installment of the international Dragons' Den format on CBC. He developed a persona as a blunt, abrasive investor.

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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.

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.

March 2007: StorageNow acquired by Storage REIT

In March 2007, StorageNow was acquired by Storage REIT for $110 million. Kevin O'Leary later sold his shares, yielding a profit exceeding $4.5 million.

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.

2008: Co-hosting Discovery Project Earth

In 2008, Kevin O'Leary co-hosted Discovery Channel's Discovery Project Earth, a show exploring innovative ways to reverse climate change.

2008: Hosted Project Earth

In 2008, Kevin O'Leary hosted 'Project Earth' on the Discovery Channel.

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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: Hosting Winnipeg Comedy Festival Gala

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

2009: Appeared on Shark Tank

In 2009, Kevin O'Leary was invited to appear on Shark Tank, the American version of Dragons' Den. He has remained with the show since the beginning.

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2010: Savings & Groans Aired on CBC

In 2010, the Winnipeg Comedy Festival gala "Savings & Groans", hosted by Kevin O'Leary, aired on CBC.

2011: O'Leary Funds' assets reached $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.

2012: O'Leary Funds' assets reached $1.2 billion

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

2012: Herjavec Left Dragons' Den

In 2012, Robert Herjavec left Dragons' Den.

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January 2014: Remarks on The Lang and O'Leary Exchange

In January 2014, on The Lang and O'Leary Exchange, Kevin O'Leary made controversial remarks.

April 2014: O'Leary Mortgages Closed

In April 2014, O'Leary Mortgages closed.

September 1, 2014: Joining 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.

2014: O'Leary Left Dragons' Den

In 2014, Kevin O'Leary left Dragons' Den.

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May 5, 2015: Celebrity Jeopardy Appearance

On May 5, 2015, Kevin O'Leary appeared on Celebrity Jeopardy and received $10,000 for his charity, despite finishing in 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, 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 Canadian businessman W. Brett Wilson.

January 2016: Offer to Invest in Alberta's Economy

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.

May 2016: Conservative Party Gatherings

In May 2016, Kevin O'Leary attended Conservative Party gatherings, leading to speculation about a leadership run.

January 18, 2017: Entering Conservative Leadership Race

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

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: Dropping out of Leadership Race

On April 26, 2017, Kevin O'Leary dropped out of the Conservative leadership race and endorsed Maxime Bernier.

2018: Launching Ask Mr. Wonderful Podcast

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

2019: Starting YouTube Channel

In 2019, Kevin O'Leary began posting videos on YouTube under the title "Ask Mr. Wonderful".

2019: Expressed Skepticism About Cryptocurrency

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

May 2021: Made Allocation to Bitcoin and Invested 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. The company then renamed itself WonderFi Technologies.

August 2021: Took Ownership Stake in FTX

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.