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 Canadian businessman and television personality known as Mr. Wonderful, gained prominence through appearances on Canadian business news programs like SqueezePlay and The Lang and O'Leary Exchange, as well as reality shows Dragons' Den and Redemption Inc. He also appeared on Discovery Channel's Project Earth. He is widely recognized for his role as an investor on the American reality show Shark Tank since 2009, where he continues to evaluate and invest in budding entrepreneurs' ventures.

Sections (4)

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

2006: Self-Referral as "Mr. Wonderful"

In 2006, Kevin O'Leary already referred to himself as "Mr. Wonderful" in a casting video for Dragon's Den, predating either that show or Shark Tank.

2008: Co-hosting Discovery Project Earth

In 2008, Kevin O'Leary co-hosted Discovery Channel's Discovery Project Earth, a show focusing on innovative climate change reversal methods.

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2009: Beginning of The Lang and O'Leary Exchange

In 2009, Kevin O'Leary began appearing with journalist Amanda Lang on CBC News Network's The Lang and O'Leary Exchange.

2009: Hosting Savings & Groans at Winnipeg Comedy Festival

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

2010: Savings & Groans aired on CBC

In 2010, the Savings & Groans show that Kevin O'Leary hosted was aired on CBC.

2011: Criticism of Chris Hedges on The Lang & O'Leary Exchange

During a segment of The Lang & O'Leary Exchange in 2011 about Occupy Wall Street protests, Kevin O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges, leading to controversy and a CBC ombudsman finding O'Leary in violation of journalistic standards.

2012: Co-production and Hosting of 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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2013: O'Leary on the Origin of "Mr. Wonderful" Nickname

In a 2013 interview, Kevin O'Leary implied he couldn't recall how he got the "Mr. Wonderful" nickname, even though he had used it himself earlier.

September 1, 2014: Return to Discovery Channel as Contributor

On September 1, 2014, Kevin O'Leary rejoined the Discovery Channel as a contributor for its radio and television stations, including CTV, after previously co-hosting SqueezePlay.

May 5, 2015: Appearance on Celebrity Jeopardy

On May 5, 2015, Kevin O'Leary appeared on Celebrity Jeopardy, earning $10,000 for charity despite finishing third with negative points.

January 2016: Offer to Invest in Alberta's Economy

In January 2016, Kevin O'Leary offered to invest $1 million in Alberta's economy if Premier Rachel Notley resigned.

February 2016: Criticism from Maxime Bernier

In February 2016, Conservative politician Maxime Bernier criticized Kevin O'Leary for wanting to be prime minister without speaking French, prompting O'Leary to take French lessons.

February 2016: Presentation at Conservative Conference

In late February 2016, Kevin O'Leary presented "If I Run, This is How" at a federal Conservative conference, predicting the Liberal government's collapse within four years.

May 2016: Attendance at Conservative Party Gatherings

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

January 18, 2017: Entry into Conservative Leadership Race and Reactions

On January 18, 2017, Kevin O'Leary officially entered the Conservative leadership race, leading to mixed reactions from former Dragons' Den co-stars Arlene Dickinson and W. Brett Wilson.

February 1, 2017: Controversy over Gun Range Video

On February 1, 2017, Kevin O'Leary posted a video of himself shooting at a Miami gun range, which was later removed from Facebook due to its insensitive timing during the funeral for victims of the Quebec City mosque shooting. O'Leary apologized for the post.

April 26, 2017: Withdrawal from 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.

2017: Speculation about Conservative Leadership Election

Following Stephen Harper's resignation, Kevin O'Leary's attendance at Conservative Party gatherings in 2016 led to speculation about him running for the 2017 leadership election.

2017: Description of 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".

November 2018: Lawsuit against Elections Canada

In November 2018, Kevin O'Leary sued Elections Canada over campaign finance laws, arguing they limited candidates' spending and discouraged wealthy individuals from running.

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 the Leadership Race

In 2017 Kevin O'Leary stated that the reason he dropped out of the leadership election was that without the support in Quebec, it would be difficult to beat Trudeau in 2019.

2021: Appearance on CNBC's Money Court

In 2021, Kevin O'Leary appeared alongside Katie Phang and Ada Pozo on CNBC's Money Court, adjudicating financial disputes.

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2024: Comments on 2024 U.S. Presidential Election

During the U.S. presidential election of 2024, Kevin O'Leary criticized Democratic presidential candidate Kamala Harris, and defended Trump for bank fraud, suggesting that it was a victimless crime. 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 and Support for US-Canada Integration

Amid President Donald Trump's threats in 2025 to impose tariffs and annex Canada, Kevin O'Leary visited Trump at Mar-a-Lago and voiced support for integrating Canada into the United States.