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 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*.

Sections (4)

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

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.

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.

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.

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.

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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.

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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, 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: Hosting Project Earth

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

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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.

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2009: Appearance on Shark Tank

In 2009, Kevin O'Leary appeared on the American version of Dragons' Den, Shark Tank. He has remained with Shark Tank since the beginning.

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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: 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.

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2012: Departure from Dragons' Den

In 2012, Kevin O'Leary left Dragons' Den, the Canadian version, but continued on Shark Tank.

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2012: O'Leary Funds Manages $1.2 Billion

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

2013: O'Leary discusses the "Mr. Wonderful" nickname

In a 2013 interview, Kevin O'Leary discussed his nickname "Mr. Wonderful", implying he couldn't remember how he got it, despite having used it himself prior to his appearances on Dragons' Den and Shark Tank.

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).

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.

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2014: Departure from Dragons' Den

In 2014, Kevin O'Leary left Dragons' Den, the Canadian version, but continued on Shark Tank.

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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: 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.

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.

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.

2018: Hosting "Ask Mr. Wonderful" podcast

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

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.