Terence Thomas Kevin O'Leary (born 9 July 1954) is a Canadian businessman, author, politician, and television personality. He co-founded O'Leary Funds and SoftKey. From 2004 to 2014, he appeared on various Canadian television shows, including the business news programmes SqueezePlay and The Lang and O'Leary Exchange, as well as the reality television shows Dragons' Den and Redemption Inc. In 2008, he appeared on Discovery Channel's Project Earth. Since 2009, he has appeared on Shark Tank, the American equivalent of Dragons' Den.
O'Leary in 2012
9 July 1954
Montreal, Quebec, Canada
|Other names||Mr. Wonderful|
|Education||University of Waterloo (BS)|
University of Western Ontario (MBA)
|Known for||Reality TV star,|
CNBC and BNN contributor,
Venture capital investor
Linda O'Leary (m. 1990)
O'Leary co-founded SoftKey Software Products, a technology company that sold software geared toward family education and entertainment. During the late 1980s and 1990s, SoftKey acquired rival companies such as Compton's New Media, The Learning Company and Brøderbund. SoftKey later changed its name to The Learning Company, and was acquired by Mattel in 1999, with the sale making O'Leary a multimillionaire. O'Leary was soon fired by Mattel after the acquisition resulted in significant losses and multiple shareholder lawsuits.
In 2017, he campaigned to be the leader of the Conservative Party of Canada. He was a frontrunner in the polls during much of that time, but dropped out in April 2017, one month before the election, citing a lack of support in Quebec.
Early life and education
O'Leary was born in Montreal, Quebec, Canada, one of two sons of Georgette (née Bukalam; 1919-2008), a small-business owner and investor of Lebanese descent, and Terry O'Leary, a salesman of Irish descent. Kevin's brother is Shane O'Leary. Due to his paternal heritage, O'Leary also holds Irish citizenship and carries an Irish passport.
O'Leary's parents divorced when he was a child, largely due to his father's alcoholism. His father died shortly thereafter. After his father's death, his mother ran the business as an executive. His mother later married an economist, George Kanawaty, who worked with the UN's International Labour Organization. His stepfather's international assignments caused the family to move frequently, and O'Leary lived in many places while growing up, including Cambodia, Tunisia, and Cyprus. O'Leary attended Stanstead College and St. George's School, both in Quebec.
O'Leary's mother was a skilled investor, investing a third of her weekly paycheque in large-cap, dividend-paying stocks and interest-bearing bonds, ultimately achieving high returns in her investment portfolio. She kept her investment portfolio secret, so O'Leary only discovered his mother's skill as an investor after her death, when her will was executed. Many of his investment lessons came from his mother, including the admonition to save one-third of his money.
O'Leary had aspired to become a photographer, but on the advice of his stepfather attended university, where he continued to develop his interest in business and investing. He received an honours bachelor's degree in environmental studies and psychology from the University of Waterloo in 1977 and an MBA in entrepreneurship from the Ivey Business School at the University of Western Ontario in 1980.
In 1979, between the first and second years of his MBA program, 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. O'Leary credits his later success at The Learning Company to the skills he developed in marketing during his days at Nabisco.
After leaving Nabisco, O'Leary began a brief career as a television producer. With two of his former MBA classmates, Scott Mackenzie and Dave Toms (both of whom had assisted on O'Leary's MBA documentary), O'Leary co-founded Special Event Television (SET). SET was an independent television production company that produced original sports programming such as The Original Six, Don Cherry's Grapevine and Bobby Orr and the Hockey Legends. The company achieved limited success with minor television shows, soccer films, sports documentaries, and short in-between-period commercials for local professional hockey games. One of his partners later bought out his share of the venture for $25,000.
After selling his share of SET, O'Leary started Softkey in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock. The company was a publisher and distributor of CD-ROM-based personal computer software for Windows and Macintosh computers. A major financial backer who had committed $250,000 in development capital to the company backed out the day before signing the documents and delivering his cheque, which left O'Leary looking for funding to support the fledgling business. He used the proceeds from the sale of his share of SET and convinced his mother to lend him $10,000 in seed capital to establish SoftKey Software Products.
The software and personal-computer industries were growing rapidly in the early 1980s, and O'Leary convinced printer manufacturers to bundle Softkey's program with their hardware. With distribution assured, the company developed a number of educational software products focused on mathematics and reading education. Softkey products typically consisted of software intended for home users, especially compilation discs containing various freeware or shareware games packaged in "jewel-case" CD-ROMs.
Softkey weathered stiff competition from other software companies in the late 1980s and prospered throughout the 1990s. By 1993, Softkey had become a major consolidator in the educational software market, acquiring rivals such as WordStar and Spinnaker Software. In 1995, Softkey acquired The Learning Company (TLC) for $606 million, adopting its name, and moved its headquarters to Cambridge, Massachusetts.
TLC lost $105 million (US) in 1998 on revenues $800 million and suffered losses over the previous two years. TLC bought its former rival Brøderbund in June 1998 for $416 million.
In 1999, TLC was acquired by Mattel for US$4.2 billion. Sales and earnings for Mattel soon dropped, and O'Leary departed Mattel. The purchase by Mattel was later called one of the most disastrous acquisitions in recent history. Following the acquisition, Mattel experienced a US$105 million loss where management had projected a $50 million profit. Mattel's stock dropped, wiping out US$3 billion of shareholder value in a single day. Mattel's shareholders later filed a class-action lawsuit accusing Mattel executives, O'Leary, and former TLC CEO Michael Perik of misleading investors about the health of TLC and the benefits of its acquisition. The lawsuit alleged that TLC used accounting tricks to hide losses and inflate quarterly revenues. O'Leary and his defendants disputed all of the charges. Mattel paid $122 million to settle the lawsuit in 2003. O'Leary blamed the technology meltdown and a culture clash of management of the two companies for the failure of the acquisition.
O'Leary and backers from Citigroup made an unsuccessful attempt to acquire the video game company Atari, and O'Leary made plans to start a video-gaming television channel that never came to fruition.
In 2003, O'Leary became a co-investor and director at StorageNow Holdings, a Canadian developer of climate-controlled storage facilities, a company controlled by Reza Satchu and Asif Satchu. StorageNow became the operator of storage services in Canada, with facilities in 11 cities, and was acquired by in Storage REIT in March 2007 for $110 million. He sold his shares, originally worth $500,000, for more than $4.5 million.
In May 2005, Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful-dismissal lawsuit, charging that they had altered an agreed-upon compensation deal and illegally reduced Wheeler's share of the profits. O'Leary and Satchu claimed Wheeler failed to reach performance targets. The case was settled out of court.
In March 2007, O'Leary joined the advisory board of Genstar Capital, a private equity firm that focuses on investing in healthcare services, industrial technology, business services and software. Genstar Capital appointed O'Leary to its Strategic Advisory Board to seek new investment opportunities for its $1.2 billion fund.
In 2008, O'Leary co-founded O'Leary Funds Inc., a mutual fund company focused on global yield investing. He is the company's chairman and lead investor, while his brother Shane O'Leary serves as the director. The fund's assets under management grew from $400 million in 2011 to $1.2-billion in 2012. The fund's primary manager was Stanton Asset Management, a firm controlled by the husband-and-wife team of Connor O'Brien and Louise Ann Poirier.
According to research by Mark R. McQueen, the fund increased distribution yield from his funds by returning invested capital to shareholders. While this is not unusual, it was contrary to O'Leary's statements. Another analysis also found that one quarter of the distributions from one of O'Leary's funds were return of capital.
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. At the time of the agreement, O'Leary Funds reported that it had taken steps to correct the violations. On 15 October 2015, O'Leary Funds was sold to Canoe Financial, a private investment-management company owned by Canadian businessman W. Brett Wilson, who once was an investor with O'Leary on CBC's Dragons' Den.
ETF and investing
On 14 July 2015, O'Leary launched an ETF through O'Shares Investments, a division of his investment fund, O'Leary Funds Management LP, where O'Leary serves as chairman. A value investor, he has given advice on personal finance. He advocates portfolio diversification and suggests that investors have their age as the percentage of bonds in their portfolios (i.e., 30% in bonds and 70% in stocks for a 30-year old investor, with an increasing proportion of bonds and decreasing proportion of stocks as the investor ages). O'Leary has also "stated on many occasions that he won’t invest in a publicly traded stock unless it pays him a dividend."
O'Leary also ventured into gold investing, with five percent of his financial portfolio invested in physical gold. However, he does not invest in stocks of gold-mining companies because he says cash flow is an important investment factor to him. O'Leary also advises diversification in multiple industry sectors so that no more than 20% of one's financial portfolio is held in one sector.
In September 2011, O'Leary released his first book, Cold Hard Truth: On Business, Money & Life, in which he shares his views on entrepreneurship, business, finance, money and life. A sequel, The Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, was published in 2012. It focused on financial literacy and financial education as a foundation for achieving wealth. O'Leary released a followup in 2013 in which he covers subjects relating to important life choices: education, careers, marriage and family, and retirement. He discusses the obstacles of raising a family while working to provide financial security for them and gives advice for developing financial literacy in family members, saving and investing money, and managing debt and credit.
Dragons' Den and Shark Tank
In 2006, O'Leary appeared as one of the five venture capitalists on the then-new show Dragons' Den on CBC, the Canadian installment of the international Dragons' Den format. On the show, O'Leary developed a persona as a blunt, abrasive, bullying investor, who at one point told a contestant who started crying, "Money doesn't care. Your tears don't add any value." This television persona was encouraged by executive producer Stuart Coxe, who during the first two seasons occasionally asked O'Leary to be "more evil". Dragons' Den became one of the most-watched shows in CBC history, with around two million viewers per episode. Coxe attributed the show's success in large part to O'Leary's presence.
In 2009, the American version of Dragons' Den, Shark Tank, began, and Shark Tank executive producer Mark Burnett invited two of the CBC Dragons' Den investors, O'Leary and Robert Herjavec, to appear on the show. Both have remained with Shark Tank since the beginning. For several years, they appeared on both shows, although Herjavec left Dragons' Den in 2012, and O'Leary left in 2014. Shark Tank became a ratings hit, averaging 9 million viewers per episode at its peak in the 2014-15 season. It has also been a critical favorite, winning the Primetime Emmy Award for Outstanding Structured Reality Program three times.
O'Leary's appearances on Dragons' Den and Shark Tank popularized the nickname "Mr. Wonderful" for him; he has said that he is often referred to by that name in public. O'Leary has said that the nickname serves both as a tongue-in-cheek reference to his reputation for being mean, as well as a reflection of his view that his blunt assessments are helpful to misguided entrepreneurs. In a 2013 interview, O'Leary implied that he could not remember how he got the nickname. He had already referred to himself as "Mr. Wonderful" in a 2006 casting video for Dragon's Den, predating either show.
Besides his blunt persona, O'Leary also gained a reputation on both shows for preferring deals in which he loans the entrepreneurs money in exchange for a percentage of future revenue, rather than taking a share of the company.
Notable deals in which O'Leary has been involved on Shark Tank include investments in Talbott Teas (later bought by Jamba Juice) and GrooveBook (later bought by Shutterfly), the latter with Mark Cuban. O'Leary has a holding company, called "Something Wonderful", for managing his Dragons' Den and Shark Tank investments.
Discovery Channel's Discovery Project Earth
The Lang and O'Leary Exchange
In 2009, O'Leary began appearing with journalist Amanda Lang on CBC News Network's The Lang and O'Leary Exchange. During a segment of The Lang & O'Leary Exchange on the Occupy Wall Street protests in 2011, O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges for sounding "like a left-wing nutbar." Hedges said afterwards that "it will be the last time" he would appear on the show and compared the CBC to Fox News. CBC's ombudsman found O'Leary's behaviour to be a violation of the public broadcaster's journalistic standards.
In January 2014, on The Lang and O'Leary Exchange, O'Leary remarked,
O'Leary later clarified these statements, saying,
O'Leary has produced and hosted his own reality show, Redemption Inc., in which he tries to help ex-convicts start and develop their own businesses. Having also been a co-host of SqueezePlay on Bell Media's Business News Network (BNN), he returned to the Discovery Channel on 1 September 2014 to join as a contributor for its radio and television stations such as CTV.
On 5 May 2015, O'Leary made an appearance on the game show Celebrity Jeopardy and received $10,000 for his charity despite finishing 3rd and in negative points after both Double Jeopardy and Final Jeopardy rounds. In September of that year, O'Leary appeared as a celebrity judge in the 95th Miss America pageant.
In January 2016, O'Leary offered to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley and appeared with four other prospective leadership candidates at a conference for federal Conservatives in late February 2016 where he gave a presentation titled "If I Run, This is How." During his speech he predicted that the Liberal government would fall within four years from economic collapse.
2017 federal Conservative Party leadership race
Following Stephen Harper's resignation as leader of the Conservative Party of Canada, O'Leary attended Conservative party gatherings in February and May 2016, leading to public speculation about whether he would run for 2017 leadership election.
In February 2016, Maxime Bernier, a Conservative Quebecois politician, criticized O'Leary, calling him a "tourist" for wanting to be prime minister without being able to speak French. Bernier later explained that he wanted all leadership candidates to learn French and praised his fellow leadership contender Lisa Raitt, who was trying to improve her French. O'Leary stated that he was taking French lessons, and promised to learn French in time for the next federal election.
On 18 January 2017, O'Leary officially entered the Conservative leadership race. That same day, his former Dragons' Den co-star Arlene Dickinson stated that she found O'Leary to be too "self-interested and opportunistic" to be qualified for the office of prime minister. In response, another former Dragons' Den co-star, W. Brett Wilson, endorsed O'Leary, highlighting differences between O'Leary as a businessman and his TV persona.
On 1 February 2017, O'Leary posted a video of himself shooting in a Miami gun range. It was removed from Facebook out of respect for the funeral for three victims of the Quebec City mosque shooting on that day. It was also revealed that he was in New York promoting one of his business ventures when this occurred. O'Leary later apologized for the timing of this post.
Throughout his run for the leadership of the Conservative Party of Canada, O'Leary was compared in the press to U.S. President Donald Trump. Commentators noted that both were wealthy businessmen who gained greater fame as a result of appearing on reality television, prior to running for office, on a platform that included lowering taxes and regulations. Some commentators also found similarities in what they called both men's brash, outspoken style, though various also stated that O'Leary's bluntness, unlike Trump's, was simply part of a "carefully-cultivated persona".
O'Leary has praised Trump personally, calling him "smart as a fox", but tended to dismiss comparisons to him by noting that, in contrast to Trump's anti-immigration rhetoric and specifically his pledge to build a wall on the Mexico–United States border, "I'm of Lebanese-Irish descent, I don't build walls, I am very proud of the society we're building in Canada, I think it is the envy of the planet. There's no walls in my world. I wouldn't exist if Canada had walls." Other commentators pointed out the differences between Trump and O'Leary on other issues, including free trade, abortion, same-sex marriage, marijuana legalization and the future of NATO.
O'Leary was a frontrunner in the polls throughout most of his run. Nevertheless, he dropped out of the leadership race on April 26, 2017, stating that, though he still thought he could win the leadership election, a lack of support for him in Quebec meant that it would be difficult for him to beat Trudeau in 2019, and that it would thus be "selfish" of him to continue. On dropping out, he endorsed Bernier, considered the other main frontrunner for the position. (Andrew Scheer eventually won the leadership election, narrowly edging out Bernier.)
Economy and trade
O'Leary supports multi-lateral free trade agreements such as the North American Free Trade Agreement. He described hypothetical trade negotiations between Donald Trump and Justin Trudeau as "Godzilla versus Bambi". O'Leary believes corporate tax rates in Canada are too high, and has promised to eliminate the national carbon tax. O'Leary has threatened to punish provinces by withholding transfer payments if they do not eliminate their respective carbon taxes. O'Leary is a critic of deficit spending and supports eliminating the national debt.
O'Leary opposes control of the CRTC over Canada's telecommunications system.
O'Leary supports building a pipeline from the Athabasca oil sands to Eastern Canada with the intentions of making Canada "energy independent". He has criticized Canada's reliance on Saudi Arabia for oil and gas. He has stated he would support a national referendum on the issue of pipelines.
O'Leary supports assisted suicide and cited Switzerland as a model for Canada to follow.
Foreign and military policy
O'Leary has criticized Justin Trudeau's procurement plan. He supports purchasing aerial combat drones to defend Canadian airspace and supports phasing out use of the Lockheed CP-140 Aurora citing cost reasons. He has criticized the lack of funding of the Canadian Armed Forces and supports spending the NATO recommended 2% of GDP on military expenditures.
In a 2017 interview with Evan Solomon, O'Leary suggested that Senators should pay money every year, instead of being paid, thus turning "a cost centre to Canada" into "a profit centre."
Leadership debt and lawsuit
In November 2018, O'Leary hired lawyer Joseph Groia and sued Elections Canada and Canada's federal elections commissioner over campaign finance laws which limited candidates to spending only $25,000 of their own money for their leadership campaign. At the time of the lawsuit, O'Leary still owed $430,000 to creditors. O'Leary had proposed to Elections Canada that he pay off the debt now with his own money and fundraise the money later, but was rebuffed, since this would be illegal. O'Leary made public statements that the law promoted mediocrity since rich people would be discouraged from running and hurt the businesses who had pledged money for his failed leadership campaign.
In O'Leary's legal submissions, he argued that the laws preventing the use of personal money over $25,000 were a restriction of his Section 2 Charter right to free expression and the threat of jail time in those laws violated his Section 7 right to security of the person.
O'Leary and his wife, Linda, have been married since 1990. The couple separated in 2011, but resumed their marriage after two years. Linda now serves as the VP of Marketing for O'Leary Wines. They have two children. Trevor is a music producer and DJ while Savannah is a multimedia producer at the Huffington Post. In an interview with Inc. Magazine writer Brian D Evans 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."
O'Leary is a fan of the football team the New England Patriots, and claims to watch all of their games, even when he is traveling around the world and the games occur during the middle of the night. He is a wine aficionado, and belongs to the Confrérie des Chevaliers du Tastevin, an international association of burgundy wine enthusiasts. He is also a lifelong photographer, and has exhibited and sold prints of his photographs, donating the proceeds to charity.
On August 24, 2019, O'Leary was involved in a fatal crash on Lake Joseph in Muskoka, Ontario. A 64-year-old man and a 48-year-old woman died when a boat owned by O'Leary was involved in a collision with another boat. O'Leary said in a statement that he is cooperating with the police investigation, that he was a passenger in his boat, and that the other boat did not have its lights on and "fled the scene". The police stated that both boats left the scene to "attend a location and both parties called 911." On September 24, Linda O'Leary, the operator of the O'Leary's boat, was charged with "careless operation of a vessel" under the small vessel regulations of the Canada Shipping Act, a charge that carries a maximum 18 months imprisonment and a $1-million fine. The driver of the other boat, Richard Ruh of Orchard Park, New York, was charged with "failing to exhibit navigation light while underway." On October 11, the Public Prosecution Service of Canada ruled out any jail time for Linda.
- O'Leary, Kevin (2011). Cold Hard Truth: On Business, Money & Life. Doubleday. ISBN 9780385671750. Retrieved 8 July 2015.
- Daniela Cambone (9 May 2012). "Kevin O'Leary's 'Cold, Hard, Truth' on Gold Investing". Forbes. Retrieved 31 July 2015.
- "Kevin O'Leary – from Dragon's Den to Redemption Inc". The Montrealer.
- "Leading Canadian Entrepreneur Kevin O'Leary Named to Genstar Strategic Advisory Board". CNW. 1 August 2007. Retrieved 31 July 2015.
- "Kevin O'Leary: He's not a billionaire, he just plays one on TV". The Globe and Mail. Toronto. 28 September 2012.
- "Kevin O'Leary makes late entry into Conservative leadership race". 18 January 2017.
- "Kevin O'Leary drops out of Conservative leadership race and will support rival Maxime Bernier". National Post. Retrieved 26 April 2017.
- Jason McBride. "Operation O'Leary". Toronto Life.
- O'Leary, Kevin (2011). Cold Hard Truth: On Business, Money & Life. Doubleday.
- Allemang, John. "Kevin O'Leary: The shark who swims alone", The Globe and Mail, 23 September 2011.
- Schlesinger, Joel. "The dragon's pen: Reality TV villain writes about life and money in new autobiography", Winnipeg FreePress, 1 October 2011.
- "O'Leary spent almost all of the 1st week of his campaign in the U.S."
- "Kevin O'Leary – from Dragon's Den to Redemption Inc". The Montrealer. 1 February 2012. Retrieved 31 July 2015.
- "Georgette Kanawaty's Obituary on Ottawa Citizen". Ottawa Citizen.
- Jane MacDougall. "Dragons' Den star Kevin O'Leary has another passion—photography". Maclean's.
- "Shark Tank : Week 19: LuminAID, Taaluma Totes, Keen Home, Scholly - Season 6 Episode 19 Recap". ABC.
- "Breakaway - Kevin O'Leary and his Townships past". cbc.ca. 3 September 2014.
- Laura Rosenfeld. "Who Is Kevin O'Leary's Wife? Linda Is Mrs. Wonderful & Totally Lives Up to the Name". Bustle. Retrieved 12 April 2015.
- "T. Kevin O'Leary". uwo.ca.
- "The Kevin O'Leary machine". The Globe and Mail. Toronto. 6 September 2012.
- "Kevin O'Leary's best advice from his 20s". Business Insider. 28 July 2015.
- O'Leary, Kevin. (2012) Cold Hard Truth on Men, Women & Money. Doubleday Canada, page 106
- "Kevin T. O'Leary". Bloomberg. Retrieved 31 July 2015.
- "T. Kevin O'Leary". Ivey Business School, University of Western Ontario. Retrieved 8 July 2015.
- "Be Like a Magpie". The Huffington Post. 19 April 2015.
- "The secret of Softkey's success". Strategy Online. 16 November 1992. Retrieved 31 July 2015.
- "Kevin O'Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons". Toronto Life. Archived from the original on 4 August 2015. Retrieved 31 July 2015.
- Ellen Ashton-Haiste (24 August 2013). "The Real Kevin O'Leary". Forever Young Information. Retrieved 31 July 2015.
- "Shark Tank - Latest News - From cameraman to Mr. Wonderful: Kevin O'Leary on where he started and what's coming up on 'Shark Tank'". CTV.ca.
- "Kevin O'Leary, TV's 'Shark Tank' Guru: In Real Life, No Business Whiz". Time. 10 September 2009.
- Steve Burgess. "Kevin O'Leary". NUVO Magazine.
- "'Shark Tank' investor Kevin O'Leary explains how a $10,000 loan from his mother helped him build a $4 billion company". businessinsider.com. 17 April 2015. Retrieved 19 January 2017.
- Willett, Shawn (24 May 1993). "Merger is first step to a consumer orientation for WordStar". InfoWorld. p. 31. Retrieved 6 March 2011.
- Bergin, Thomas J. (October–December 2006). "Word Processing Timeline". IEEE Annals of the History of Computing. Retrieved 6 March 2011.
- "Softkey Reaches Agreement to Buy Learning Company". nytimes.com. 8 December 1995. Retrieved 19 January 2017.
- Joe Castaldo. "Kevin O'Leary: The natural". Canadian Business.
- Cave, Andrew. "Mattel sale ends $3.6bn fiasco". Telegraph.co.uk. Retrieved 20 January 2017.
- Gandel, Stephen (10 September 2009). "TV's Shark Tank Guru: In Real Life, No Business Whiz". Time. ISSN 0040-781X. Retrieved 20 January 2017.
- Dunfield, Allison (5 May 2008). "Reza Satchu, 38". The Globe and Mail. Retrieved 25 November 2019.
- "A history of Kevin O'Leary's spotty business record, in four deals". Canadian Business. 19 January 2017. Retrieved 17 October 2017.
- "Leading Canadian Entrepreneur Kevin O'Leary Named to Genstar Strategic Advisory Board". PNR. 1 August 2007. Retrieved 31 July 2015.
- Oysey, Dan (1 May 2012). "Kevin O'Leary and Connor O'Brien use celebrity branding to take on Canada's fund managers". Financial Post. Retrieved 19 January 2016.
- "Kevin O'Leary's business history back in spotlight after entering race for Conservative Party leader". Financial Post. Retrieved 17 October 2017.
- "Gestion de fonds O'Leary to pay $38,000 in administrative penalties". lautorite.qc.ca. Retrieved 6 September 2016.
- Cain, Terry (15 October 2015). "Dragons reunite as Canoe picks up Kevin O'Leary's fund shop". Business News Network. Retrieved 15 January 2016.
- "About O'Leary Ventures". O'Leary Ventures. Retrieved 25 July 2013.
- "O'Leary Wines". Retrieved 25 July 2013.
- "O'Leary Fine Wines Wins "Best Value" at InterVin International Wine Awards". Retrieved 25 July 2013.
- McLister, Rob. "O'Leary Mortgages Is No More". CanadianMortgageTrends.com. 10 April 2014
- Nelson Smith (28 April 2016). "Steal These 4 Investing Tips from Kevin O'Leary". Motley Fool.
- Smith, Nelson (16 April 2016). "Collect $1,000 per month by investing like Kevin O'Leary".
- "Kevin O'Leary's 'Cold, Hard, Truth' on Gold Investing". Forbes. 5 November 2012. Retrieved 9 November 2014.
- "Three investment tips from a dragon". Ontario Farmer. Retrieved 9 November 2014.
- "Kevin O'Leary on Dividend Investing". Spiked Finance. 3 May 2014. Retrieved 9 November 2014.
- O'Leary, Kevin. Cold Hard Truth on Men, Women, and Money. Simon and Schuster.
- Padanyi, Matt (18 December 2015). "Kevin O'Leary tells a young investor how to turn $10,000 in a nest egg". BNN. Retrieved 15 January 2016.
- "Kevin O'Leary: The shark who swims alone". The Globe and Mail. Toronto. Retrieved 6 August 2012.
- "Order your copy of Cold Hard Truth on Men, Women & Money". Doubleday Canada. Retrieved 25 July 2013.
- "Cold Hard Truth on Family, Kids and Money". Penguin Random House Canada. Retrieved 1 August 2015.
- Henderson, J. Maureen (20 January 2017). "Why Shark Tank's Kevin O'Leary Is Not The Next Donald Trump". Forbes.
- Bambury, Brent (6 January 2017). "Meet the man who helped Kevin O'Leary shape his powerful personal brand". CBC Radio.
- "Full 2014–15 Series Rankings". Deadline Hollywood. 22 May 2015. Archived from the original on 22 May 2015. Retrieved 22 May 2015.
- "Shark Tank – Awards & Nominations". Academy of Television Arts & Sciences. Retrieved 6 January 2017.
- Malamut, Melissa (10 October 2013). "Q&A: Shark Tank's Kevin O'Leary". Boston Magazine.
- Vivian Giang (25 November 2013). "What It's Like Working With the Meanest Investor on "Shark Tank"". Business Insider. Retrieved 5 February 2016.
- "Kevin O'leary Mr Wonderful from his Audition tape for CA Dragons Den". YouTube.
- Ho, Ky Trang (10 April 2016). "Shark Tank's Kevin O'Leary: How Debt And Licensing Deals Can Benefit Entrepreneurs More". Forbes.
- Shropshire, Corilyn (21 February 2012). "Jamba Juice buys Talbott Teas". Chicago Tribune.
- Perez, Sarah (17 November 2014). "Shark Tank-Backed GrooveBook Acquired By Shutterfly For $14.5 Million". TechCrunch.
- "Discovery". Discovery. Archived from the original on 7 August 2012.
- Colin Dodds (12 August 2014). "Kevin O'Leary: Success Story". Toronto Star.
- James Crugnale (12 October 2011). "Journalist Chris Hedges Argues With CBC's Kevin O'Leary: 'This Sounds Like Fox News And I Don't Go On Fox News!'", Mediaite; retrieved 24 January 2014.
- Szklarski, Cassandra. "O'Leary's 'nutbar' remark breach of policy, CBC ombudsman says." Globe & Mail, 14 October 2011; retrieved 23 March 2012.
- "Kevin O'Leary Goes Off On Thomas Piketty, And It's Embarrassing (VIDEO)". The Huffington Post. 5 May 2014.
- Kludt, Tom (22 January 2014). Businessman, TV Host: It's 'Fantastic' That 85 People Have More Wealth Than Billions In Poverty (VIDEO). Talking Points Memo; retrieved 22 January 2014.
- Martin, Abby (23 January 2014). "Orwell's Kiev, warnings from BP employees, 4 years of corporate personhood", Breaking the Set; retrieved 24 January 2014.
- Hulsman, Noel (22 January 2014). "Kevin O'Leary thinks global wealth gap is 'fantastic news'", Yahoo News; retrieved 31 January 2014.
- Esther Enkin (6 March 2014). "O'Leary's hyperbole". CBC Radio Canada.
- "Kevin O'Leary, Bruce Croxon leaving CBC's Dragon's Den". CBC.ca. 13 March 2014. Retrieved 14 March 2014.
- "Former 'Dragon' Kevin O'Leary leaves CBC to join CTV". Toronto Star. 12 August 2014. Retrieved 17 October 2017.
- Daro, Ishmael N. (13 May 2015). "Kevin O'Leary did not do very well on Celebrity Jeopardy!". National Post. Retrieved 25 August 2015.
- Field, Sarah. "How Miss America Judges Can Impress Judge Kevin O'Leary". Inquisitr.com. The Inquisitr. Retrieved 13 January 2016.
- FRANCOIS MARCHAND. "Put your head on my (virtual) shoulder: Paul Anka sings past classics while embracing the future in hologram technology". www.vancouversun.com.
- "Kevin O'Leary circling as key Conservatives test Tory leadership waters". CBC News. 14 January 2016. Retrieved 14 January 2016.
- "Potential Tory leadership candidates test waters at weekend conference". CTVNews. Retrieved 28 February 2016.
- "5 auditions to lead the post-Harper Conservatives". cbc.ca. Retrieved 17 October 2017.
- Naumetz, Tim. "Leary shakes up Manning conference, predicts economic collapse, Liberal turmoil". hilltimes.com. The Hill Times. Retrieved 17 October 2017.
- "Will he or won't he? The Conservatives' Kevin O'Leary factor". Macleans.ca. 26 May 2016. Retrieved 13 March 2017.
- ICI.Radio-Canada.ca, Zone Nouvelles. ""Un touriste!: "Maxime Bernier s'en prend à l'ex-dragon Kevin O'Leary"". Radio-Canada.ca (in French). Retrieved 28 February 2016.
- "Maxime Bernier slams English-only Kevin O'Leary". Toronto Sun. Retrieved 28 February 2016.
- "Kevin O'Leary may speak jobs, but it's French that Quebecers want to hear from next Tory leader, says Bernier". Globe and Mail. Retrieved 1 March 2016.
- "O'Leary shows off his French lessons, promises proficiency by 2019". Retrieved 17 October 2017.
- Slaughter, Graham (18 January 2017). "Kevin O'Leary is 'self-interested' says former co-star Arlene Dickinson". CTV News. Retrieved 17 October 2017.
- Bell, David (23 January 2017). "Brett Wilson endorses Kevin O'Leary after Arlene Dickinson's scathing column". CBC. Retrieved 23 January 2017.
- Cullen, Catherine (2 February 2017). "Kevin O'Leary pulls gun range video 'out of respect' for shooting victims' funeral". CBC. Retrieved 17 October 2017.
- Canadian Press (2 February 2017). "O'Leary gun video posted on day of Mosque funeral 'insensitive:' public safety minister". Toronto Star. Retrieved 4 February 2017.
- Kennedy, Sean (25 January 2017). "Can Canada's Trump repeat the Donald's success?". CNN.com.
- Lagerquist, Jeff (4 February 2017). "Kevin O'Leary proposes 'fast-track' to citizenship for skilled immigrants". CTV News.
- Berlinger, Joshua (19 January 2017). "Canada's Donald Trump? 'Shark Tank' star Kevin O'Leary runs for Tory leadership". CNN.com.
- Elliott, Howard (19 January 2017). "The Spectator's View: Kevin O'Leary isn't like Trump. Honest". The Hamilton Spectator.
- "Could O'Leary teach millennials to love the Conservatives?". 17 January 2017.
- Hensel, Anna (7 February 2017). "Kevin O'Leary on His Run for Prime Minister and How Trump Is Doing So Far". Inc.
O'Leary says he's going to have to match Trump's corporate tax rates and his regulatory moves.
- Taube, Michael (24 January 2017). "Trump of the Great White North?". National Review.
- "Kevin O'Leary 'writing off' Kellie Leitch's Tory leadership bid". 13 September 2016.
- Mason, Gary (28 March 2017). "Kevin O'Leary: Rebel without a (notwithstanding) clause". The Globe and Mail.
- Robyn Urback (16 January 2016). "Kevin O'Leary is way too boring to be called Canada's Donald Trump: Robyn Urback". CBC News.
- Nguyen, Tina (21 January 2016). "TRUMPISM Goes to CANADA: SHARK TANK STAR MULLING RUN for PARLIAMENT". Vanity Fair.
- "'I am not Donald Trump': Kevin O'Leary denies parallels with bombastic American". Retrieved 17 October 2017.
- King, Michael (19 January 2017). "Reality TV star taking Trump-inspired politics north of the border". CBS News.
- "'I'm going to be his worst nightmare': 'Shark Tank' judge Kevin O'Leary is running to lead the Conservative Party in Canada". Business Insider.
- "Kevin O'Leary promises to scrap the carbon tax if elected prime minister".
- "Kevin O'Leary on why he's running for the Tory leadership". Maclean's.
- "Bank mergers, housing and marijuana: Kevin O'Leary on his leadership bid".
- "Kevin O'Leary: 'If I don't deliver a majority mandate in 2019, fire me'".
- O'Leary, Kevin (14 September 2016). "It's Time to End Canada's Pipeline Circus". The Huffington Post. Retrieved 23 January 2017.
- "Kevin O'Leary enters Conservative leadership race: 'I'm in'".
- "Kevin O'Leary is way too boring to be called Canada's Donald Trump".
- "Kevin O'Leary supports ending airstrikes against ISIS".
- "Kevin O'Leary on Russia". Twitter. Retrieved 17 October 2017.
- "Kevin O'Leary explains his vision for Canada, says he's 'coming' for PM Trudeau".
- "Kevin O'Leary says refugees exploiting an immigration 'loophole'". Toronto Sun. 6 March 2017.
- Kevin O'Leary [@kevinolearytv] (7 March 2017). "#2. Increase border security to halt the flow of illegals into Canada & work w/ US border security to better understand our deficiencies" (Tweet) – via Twitter.
- Kevin O'Leary [@kevinolearytv] (7 March 2017). "Illegal immigration compromises Canada's security & is a slap in the face to families who are waiting to move to our country legitimately" (Tweet) – via Twitter.
- Dehaas, Josh (15 January 2017). "Senate seats for sale? O'Leary says he'd consider it". CTV. Retrieved 17 October 2017.
- Tasker, John Paul; Kapelos, Vassy (14 November 2018). "Kevin O'Leary suing Elections Canada over fundraising limits". CBC News. Retrieved 14 November 2018.
- John Allemang. "Kevin O'Leary: The shark who swims alone". Globe and Mail. Retrieved 23 September 2011.
- "Linda O'Leary: Shark Tank Kevin O'Leary's Wife". Daily Entertainment News. Retrieved 12 April 2015.
- "Kevin O'Leary: Shark, Dragon, Dad". Inbetween Magazine. Retrieved 12 April 2015.
- McBride, Jason (24 August 2016). "Kevin O'Leary is a blowhard, a relentless self-promoter and, maybe, Canada's future leader". Toronto Life. Retrieved 25 November 2019.
- Evans, Bryan (22 September 2016). "Inside Kevin O'Leary's unconventional wealth-building habits". Retrieved 17 January 2019.
- Jason McBride (24 August 2016). "Kevin O'Leary is a blowhard, a relentless self-promoter". Toronto Life.
- Alex Boutilier (18 January 2017). "Transcript: O'Leary on his bid for Conservative leadership". The Toronto Star.
- "Where is home? Kevin O'Leary who's called Boston 'home' says his priority is Canada". Global News. 15 January 2016.
- Grundhauser, Eric (9 February 2016). "A Look At Mr. Wonderful's Secret Society for Wine Snobs". Atlas Obscura.
- Kuitenbrouwer, Peter (2 January 2015). "Tycoon Kevin O'Leary says when it comes to photography, he is "a starving artist, hold the starving"". National Post.
- "Kevin O'Leary confirms he was passenger in boat involved in double-fatal crash".
- Wilson, Codi (29 August 2019). "Man killed in boat crash involving Kevin O'Leary was 'fun-loving' father of 2, his brother says". CP24.com.
- "Kevin O'Leary's wife charged in fatal Ontario boat crash". ctvnews.ca. 24 September 2019.
- "Linda O'Leary not facing jail time for charge in fatal boat crash". toronto.ctvnews.ca. 11 October 2019.