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Terrence Thomas Kevin O'Leary (born July 9, 1954), also known as Mr. Wonderful, is a Canadian businessman and television personality. From 2004 to 2014, he appeared on various Canadian television shows, including the business news programs ''SqueezePlay'' and ''
The Lang and O'Leary Exchange ''The Exchange'' was a Canadian business news television series which aired weekdays on CBC News Network, with an overnight rebroadcast on CBC Television, from October 26, 2009 to September 9, 2016. The show originally launched as ''The Lang an ...
'', as well as the Canadian
reality television Reality television is a genre of television programming that documents purportedly unscripted real-life situations, often starring ordinary people rather than professional actors. Reality television emerged as a distinct genre in the early 1990s ...
shows ''
Dragons' Den ''Dragons' Den'' is a reality television program format in which entrepreneurs pitch their business ideas to a panel of venture capitalists in the hope of securing investment finance from them. The program originated in 2001 in Japan, where it ...
'' and '' Redemption Inc.'' In 2008, he appeared on
Discovery Channel Discovery Channel, known as The Discovery Channel from 1985 to 1995, and often referred to as simply Discovery, is an American cable channel that is best known for its ongoing reality television shows and promotion of pseudoscience. It init ...
's '' Project Earth''. Since 2009, he has appeared on ''
Shark Tank ''Shark Tank'' is an American business Reality television#Investments, reality television series that premiered on August 9, 2009, on American Broadcasting Company, ABC.Hibberd, James (May 10, 2012)Dancing,' 'Bachelor,' and a bigger 'Shark Tank ...
'', the American version of ''
Dragons' Den ''Dragons' Den'' is a reality television program format in which entrepreneurs pitch their business ideas to a panel of venture capitalists in the hope of securing investment finance from them. The program originated in 2001 in Japan, where it ...
''. 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 became a major consolidator in the global educational software market, having acquired rival companies via
hostile takeover In business, a takeover is the purchase of one company (law), company (the ''target'') by another (the ''acquirer'' or ''bidder''). In the UK, the term refers to the acquisition of a public company whose shares are publicly listed, in contrast t ...
bids, such as Compton's New Media,
the Learning Company The Learning Company (TLC) was an American educational software company founded in 1980 in Palo Alto, California and headquartered in Fremont, California. The company produced a grade-based line of learning software, edutainment games, and ...
, and
Broderbund Broderbund Software, Inc. (stylized as Brøderbund) was an American maker of video games, educational software, and productivity tools. Broderbund is best known for the 8-bit video game hits '' Choplifter'', '' Lode Runner'', '' Karateka'', and ...
. SoftKey later changed its name to The Learning Company and was acquired by
Mattel Mattel, Inc. ( ) is an American multinational corporation, multinational toy manufacturing and entertainment company headquartered in El Segundo, California. Founded in Los Angeles by Harold Matson and the husband-and-wife duo of Ruth Handler, ...
in 1999, with the sale making O'Leary a multimillionaire. Mattel promptly fired O'Leary, and the acquisition resulted in significant losses and multiple shareholder lawsuits. In 2017, he campaigned to be the leader of the
Conservative Party of Canada The Conservative Party of Canada (CPC; , ), sometimes referred to as the Tories, is a Government of Canada, federal List of political parties in Canada, political party in Canada. It was formed in 2003 by the merger of the two main Right-wing ...
. He dropped out in April 2017, one month before the election, citing a lack of support in
Quebec Quebec is Canada's List of Canadian provinces and territories by area, largest province by area. Located in Central Canada, the province shares borders with the provinces of Ontario to the west, Newfoundland and Labrador to the northeast, ...
. In addition to his native Canadian citizenship, O'Leary also holds Irish and Emirati citizenship.


Early life and education

O'Leary was born on 9 July 1954, in
Montreal Montreal is the List of towns in Quebec, largest city in the Provinces and territories of Canada, province of Quebec, the List of the largest municipalities in Canada by population, second-largest in Canada, and the List of North American cit ...
, one of two sons of Georgette (née Bookalam; ), a small-business owner and investor of Lebanese descent, and Terry O'Leary, a salesman of Irish descent. Kevin also has a brother, Shane O'Leary.Allemang, John
"Kevin O'Leary: The shark who swims alone"
''
The Globe and Mail ''The Globe and Mail'' is a Newspapers in Canada, Canadian newspaper printed in five cities in Western Canada, western and central Canada. With a weekly readership of more than 6 million in 2024, it is Canada's most widely read newspaper on week ...
'', 23 September 2011.
Due to his paternal heritage, O'Leary also holds Irish citizenship and carries an Irish passport. O'Leary has
dyslexia Dyslexia (), previously known as word blindness, is a learning disability that affects either reading or writing. Different people are affected to different degrees. Problems may include difficulties in spelling words, reading quickly, wri ...
, which he argued helped him in the world of business. O'Leary grew up in
Mount Royal, Quebec Mount Royal ( , officially Town of Mount Royal, Ville Mont-Royal, abbreviated TMR, ) is an affluent Greater Montreal, on-island suburban town located on the northwest side of the eponymous Mount Royal, northwest of Downtown Montreal, on the Isla ...
. His parents divorced when he was a child, largely due to his father's alcoholism. His father died shortly after that, when O'Leary was only seven. After his father's death, his mother ran the family's clothing business as an executive. His mother later married an economist, George Kanawaty, who worked with the UN's
International Labour Organization The International Labour Organization (ILO) is a United Nations agency whose mandate is to advance social and economic justice by setting international labour standards. Founded in October 1919 under the League of Nations, it is one of the firs ...
. His stepfather's international assignments caused the family to move frequently, and O'Leary lived in many places while growing up, including
Cambodia Cambodia, officially the Kingdom of Cambodia, is a country in Southeast Asia on the Mainland Southeast Asia, Indochinese Peninsula. It is bordered by Thailand to the northwest, Laos to the north, and Vietnam to the east, and has a coastline ...
,
Ethiopia Ethiopia, officially the Federal Democratic Republic of Ethiopia, is a landlocked country located in the Horn of Africa region of East Africa. It shares borders with Eritrea to the north, Djibouti to the northeast, Somalia to the east, Ken ...
,
Tunisia Tunisia, officially the Republic of Tunisia, is a country in the Maghreb region of North Africa. It is bordered by Algeria to the west and southwest, Libya to the southeast, and the Mediterranean Sea to the north and east. Tunisia also shares m ...
, and
Cyprus Cyprus (), officially the Republic of Cyprus, is an island country in the eastern Mediterranean Sea. Situated in West Asia, its cultural identity and geopolitical orientation are overwhelmingly Southeast European. Cyprus is the List of isl ...
. In his youth, he met both
Haile Selassie Haile Selassie I (born Tafari Makonnen or ''Ethiopian aristocratic and court titles#Lij, Lij'' Tafari; 23 July 189227 August 1975) was Emperor of Ethiopia from 1930 to 1974. He rose to power as the Ethiopian aristocratic and court titles, Rege ...
of Ethiopia and
Pol Pot Pol Pot (born Saloth Sâr; 19 May 1925 – 15 April 1998) was a Cambodian politician, revolutionary, and dictator who ruled the communist state of Democratic Kampuchea from 1976 until Cambodian–Vietnamese War, his overthrow in 1979. During ...
of Cambodia. O'Leary attended
Stanstead College Stanstead College is an English-language independent boarding school in Stanstead, Quebec, Canada, for boys and girls in Grades 7 through 12. The school is located on a campus in Quebec's Eastern Townships – just north of the Canada–United S ...
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 who prompted the young Kevin to be more realistic with his future career aspirations, ultimately led him to attend university, where he continued to develop his interest in business and investing since his youth. He received an honours bachelor's degree in
environmental studies Environmental studies (EVS or EVST) is a multidisciplinary academic field which systematically studies human behavior, human interaction with the Natural environment, environment. Environmental studies connects principles from the physical sci ...
and psychology from the
University of Waterloo The University of Waterloo (UWaterloo, UW, or Waterloo) is a Public university, public research university located in Waterloo, Ontario, Canada. The main campus is on of land adjacent to uptown Waterloo and Waterloo Park. The university also op ...
in 1977 and an MBA in entrepreneurship from
Ivey Business School Ivey Business School is the main business school of Western University, located in London, Ontario, Canada. It offers full-time undergraduate and graduate programs in London, Ontario and maintains a Toronto facility for its EMBA program and two ...
at the
University of Western Ontario The University of Western Ontario (UWO; branded as Western University) is a Public university, public research university in London, Ontario, Canada. The main campus is located on of land, surrounded by residential neighbourhoods and the Thame ...
in 1980.


Business career

In 1978, between the first and second years of his MBA program, O'Leary was selected for an internship at
Nabisco Nabisco (, abbreviated from the earlier name National Biscuit Company) is an American manufacturer of cookies and snacks headquartered in East Hanover, New Jersey. The company is a subsidiary of Illinois-based Mondelēz International. Nabisco' ...
in
Downtown Toronto Downtown Toronto is the main city centre of Toronto, Ontario, Canada. Located entirely within the district of Old Toronto, it is approximately 16.6 square kilometres in area, bounded by Bloor Street to the northeast and Dupont Street to the nor ...
and then worked as an assistant brand manager for Nabisco's cat food brand. O'Leary attributed his future business success at The Learning Company as a result of the extensive marketing skills that he honed during his assistant brand management 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 & 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.


Softkey

After selling his SET share, O'Leary then proceeded by moving onto his next business venture. He started
Softkey SoftKey International (originally SoftKey Software Products, Inc.) was a software company founded by Kevin O'Leary in 1986 in Toronto, Ontario. It was known as The Learning Company from 1995 to 1999 after acquiring The Learning Company an ...
in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock. The company was a publisher and distributor of CD-based personal computer software for
Windows Windows is a Product lining, product line of Proprietary software, proprietary graphical user interface, graphical operating systems developed and marketed by Microsoft. It is grouped into families and subfamilies that cater to particular sec ...
and
Macintosh Mac is a brand of personal computers designed and marketed by Apple Inc., Apple since 1984. The name is short for Macintosh (its official name until 1999), a reference to the McIntosh (apple), McIntosh apple. The current product lineup inclu ...
computers. A major financial supporter who had committed $250,000 in investment capital to finance O'Leary's company backed out the day before signing the documents and delivering his cheque, leaving O'Leary to go elsewhere to seek the necessary funding sources that he needed to support his fledgling business. Desperate to secure funding, O'Leary turned to using the proceeds that he gained from selling his SET share while also convincing his mother to lend him $10,000 in seed capital to establish SoftKey Software Products. As the software and personal-computer industries were proliferating throughout the course of the early 1980s, O'Leary convinced printer manufacturers to bundle Softkey's program with their hardware. With distribution assured, the company developed several educational software products focused on mathematics and reading education. Softkey products typically consisted of software for home users, especially compilation discs containing various
freeware Freeware is software, often proprietary, that is distributed at no monetary cost to the end user. There is no agreed-upon set of rights, license, or EULA that defines ''freeware'' unambiguously; every publisher defines its own rules for the free ...
or
shareware Shareware is a type of proprietary software that is initially shared by the owner for trial use at little or no cost. Often the software has limited functionality or incomplete documentation until the user sends payment to the software developer. ...
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 WordStar is a discontinued word processor application for microcomputers. It was published by MicroPro International and originally written for the CP/M-80 operating system (OS), with later editions added for MS-DOS and other 16-bit computing, ...
and
Spinnaker Software Spinnaker Software Corporation was an American software and video game company. Founded in 1982 by Bill Bowman and C. David Seuss, it was known primarily for its line of non-curriculum based educational software, which was a major seller during ...
in the process. In 1995, Softkey acquired
The Learning Company The Learning Company (TLC) was an American educational software company founded in 1980 in Palo Alto, California and headquartered in Fremont, California. The company produced a grade-based line of learning software, edutainment games, and ...
(TLC) for $606 million, adopting its name, and moved its headquarters to
Cambridge, Massachusetts Cambridge ( ) is a city in Middlesex County, Massachusetts, United States. It is a suburb in the Greater Boston metropolitan area, located directly across the Charles River from Boston. The city's population as of the 2020 United States census, ...
. TLC lost $105 million (US) in 1998 on revenues of $800 million and suffered losses over the previous two years. TLC bought its former rival
Broderbund Broderbund Software, Inc. (stylized as Brøderbund) was an American maker of video games, educational software, and productivity tools. Broderbund is best known for the 8-bit video game hits '' Choplifter'', '' Lode Runner'', '' Karateka'', and ...
in June 1998 for $416 million. In 1999, TLC was acquired by
Mattel Mattel, Inc. ( ) is an American multinational corporation, multinational toy manufacturing and entertainment company headquartered in El Segundo, California. Founded in Los Angeles by Harold Matson and the husband-and-wife duo of Ruth Handler, ...
for US$4.2 billion. Following the acquisition, sales and earnings for Mattel soon dropped, and O'Leary was fired. The purchase by Mattel was later called one of the most disastrous corporate acquisitions in recent business history. While acquisition management had projected a post-acquisition profit of US$50 million, Mattel actually experienced a loss of US$105 million. 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. In response, O'Leary and his defendants disputed all of the charges, with Mattel later paying $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 financial backers from
Citigroup Citigroup Inc. or Citi (Style (visual arts), stylized as citi) is an American multinational investment banking, investment bank and financial services company based in New York City. The company was formed in 1998 by the merger of Citicorp, t ...
made an unsuccessful attempt to acquire the French video game company
Atari Atari () is a brand name that has been owned by several entities since its inception in 1972. It is currently owned by French holding company Atari SA (formerly Infogrames) and its focus is on "video games, consumer hardware, licensing and bl ...
, with O'Leary having made plans to start a video-gaming television channel which never materialized.


StorageNow Holdings

In 2003, 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 MRC II Distribution Company, L.P., doing business as MRC (formerly Media Rights Capital), is an American film and television production company founded by Mordecai (Modi) Wiczyk and Asif Satchu in 2006. Based in West Hollywood, California, the c ...
. StorageNow became the largest operator of storage services in Canada, with facilities in 11 cities, and was acquired by Storage REIT in March 2007 for $110 million. O'Leary later sold his shares which yielded a windfall profit exceeding $4.5 million through realized capital gains, with his initial stake being originally valued at $500,000. 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.


Other ventures

In March 2007, O'Leary joined the advisory board of
Genstar Capital Genstar Capital is a private equity firm that executes leveraged buyout transactions in middle-market companies based in North America. Founded in 1988, Genstar currently has approximately $33 billion in assets under management. Based in San ...
, a
private equity Private equity (PE) is stock in a private company that does not offer stock to the general public; instead it is offered to specialized investment funds and limited partnerships that take an active role in the management and structuring of the co ...
firm that focuses on investing in health care, 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.


O'Leary Funds

In 2008, 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 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 Canadian banker Mark R. McQueen, O'Leary's 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 taking steps to correct the violations. On October 15, 2015, O'Leary Funds was sold to Canoe Financial, a private investment-management company owned by Canadian businessman W. Brett Wilson. Wilson once was an investor with O'Leary on CBC's ''Dragons' Den.''


O'Leary Ventures

O'Leary is also the founder of O'Leary Ventures, a private early-stage venture capital investment company, O'Leary Mortgages, O'Leary books, and O'Leary Fine Wines. In April 2014, O'Leary Mortgages closed. O'Leary's funds have a questionable history and are said to have declined over 20% in a year, often a big blow to fund managers. O'Leary no longer manages outside money.


ETF and investing

On July 14, 2015, O'Leary launched an
Exchange-traded fund An exchange-traded fund (ETF) is a type of investment fund that is also an exchange-traded product, i.e., it is traded on stock exchanges. ETFs own financial assets such as stocks, bonds, currencies, debts, futures contracts, and/or comm ...
(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 advised on
personal finance Personal finance is the financial management that an individual or a family unit performs to budget, save, and spend monetary resources in a controlled manner, taking into account various financial risks and future life events. When planni ...
. He advocates
portfolio diversification In finance, diversification is the process of allocating capital in a way that reduces the exposure to any one particular asset or risk. A common path towards diversification is to reduce risk or volatility by investing in a variety of assets. ...
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 publicly-traded stock unless it pays him a
dividend A dividend is a distribution of profits by a corporation to its shareholders, after which the stock exchange decreases the price of the stock by the dividend to remove volatility. The market has no control over the stock price on open on the ex ...
." O'Leary is also an active gold investor, 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 Cash flow, in general, refers to payments made into or out of a business, project, or financial product. It can also refer more specifically to a real or virtual movement of money. *Cash flow, in its narrow sense, is a payment (in a currency), es ...
is an important investment factor to him. O'Leary also advises diversification in multiple industry sectors while dedicating no more than 20 percent of one's financial portfolio being concentrated in one sector.


Cryptocurrency

O'Leary initially expressed skepticism about cryptocurrency, describing
bitcoin Bitcoin (abbreviation: BTC; Currency symbol, sign: ₿) is the first Decentralized application, decentralized cryptocurrency. Based on a free-market ideology, bitcoin was invented in 2008 when an unknown entity published a white paper under ...
as "a digital game" and "useless currency" in 2019. He illustrated his thinking with the following example, "Let's say you want to buy a piece of Swiss real estate for $10 million in bitcoin...The seller wants a guarantee that the bitcoin value comes back to the U.S. currency. You have to somehow
hedge A hedge or hedgerow is a line of closely spaced (3 feet or closer) shrubs and sometimes trees, planted and trained to form a barrier or to mark the boundary of an area, such as between neighbouring properties. Hedges that are used to separate ...
the risk of bitcoin. That means it's not a real currency. That means the receiver is not willing to take the risk of the volatility it has. It's worthless." In May 2021, O'Leary said he had made a 3 to 5% allocation to bitcoin and had become a strategic investor in the
Vancouver Vancouver is a major city in Western Canada, located in the Lower Mainland region of British Columbia. As the List of cities in British Columbia, most populous city in the province, the 2021 Canadian census recorded 662,248 people in the cit ...
-based
decentralized finance Decentralized finance (often stylized as DeFi) provides financial instruments and services through smart contracts on a programmable, permissionless blockchain. This approach reduces the need for intermediaries such as brokerages, exchanges, or ...
platform Defi Ventures; the company then renamed itself WonderFi Technologies, in reference to O'Leary's nickname, "Mr. Wonderful". In August 2021, it was announced 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. FTX subsequently went bankrupt due to CEO
Sam Bankman-Fried Samuel Benjamin Bankman-Fried (born March 5, 1992), commonly known as SBF, is an American entrepreneur who was convicted of fraud and related crimes in November 2023. Bankman-Fried founded the FTX cryptocurrency exchange and was celebrated as a ...
secretly using client funds to make speculative bets that were unsuccessful. In November 2022, O'Leary, alongside other spokespeople for FTX, was sued in a
class-action A class action A class action is a form of lawsuit. Class Action may also refer to: * ''Class Action'' (film), 1991, starring Gene Hackman and Mary Elizabeth Mastrantonio * Class Action (band), a garage house band * "Class Action" (''Teenage R ...
lawsuit. There is precedent for prosecuting individuals promoting fraudulent cryptocurrency ventures—regardless of whether they had
plausible deniability Plausible deniability is the ability of people, typically senior officials in a formal or informal chain of command, to deny knowledge or responsibility for actions committed by or on behalf of members of their organizational hierarchy. They may ...
. For example, in February 2022, the U.S. 11th Circuit Court of Appeals ruled in a lawsuit against
Bitconnect Bitconnect (stylized ''bitconnect'' and also spelled BitConnect, Ticker symbol, ticker code BCC) was an open-source cryptocurrency in 2016–2018 that was connected with a high-yield investment program, a type of Ponzi scheme. After the platform ...
that the
Securities Act of 1933 The Securities Act of 1933, also known as the 1933 Act, the Securities Act, the Truth in Securities Act, the Federal Securities Act, and the '33 Act, was enacted by the United States Congress on May 27, 1933, during the Great Depression and afte ...
extends to targeted solicitation using
social media Social media are interactive technologies that facilitate the Content creation, creation, information exchange, sharing and news aggregator, aggregation of Content (media), content (such as ideas, interests, and other forms of expression) amongs ...
. O'Leary claimed on CNBC that he was paid $15 million for the spokesman role, adding that he lost $9.7 million in digital assets, the remainder allotment in various fees and taxes, and a further million dollars' worth of equity after the company's insolvency. At an FTX hearing, O'Leary claimed that
Binance Binance Holdings Ltd., branded Binance, is the largest cryptocurrency exchange in terms of daily trading volume of cryptocurrencies. Binance was founded in 2017 by Changpeng Zhao, a developer who had previously created high-frequency trading ...
CEO
Changpeng Zhao Changpeng Zhao ( zh, s=赵长鹏, p=Zhào Chángpéng), commonly known as CZ, is a Chinese-born Canadian businessman. Zhao is the co-founder and former CEO of Binance. He resigned as the CEO in November 2023 after pleading guilty to a money lau ...
"put FTX out of business." O'Leary has been an advocate of
cryptocurrency A cryptocurrency (colloquially crypto) is a digital currency designed to work through a computer network that is not reliant on any central authority, such as a government or bank, to uphold or maintain it. Individual coin ownership record ...
investing and personally owns coins in the cryptocurrencies
Ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R ...
, A4M Ethereum Blockchain, Polygon, SOL,
Bitcoin Bitcoin (abbreviation: BTC; Currency symbol, sign: ₿) is the first Decentralized application, decentralized cryptocurrency. Based on a free-market ideology, bitcoin was invented in 2008 when an unknown entity published a white paper under ...
, and Pawthereum.


Books

* ''Cold Hard Truth: On Business, Money & Life'' (2011) * ''Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them'' (2012) * ''Cold Hard Truth on Family, Kids and Money'' (2015) * ''Cold Hard Truth on Marriage and Money: Part Two of Cold Hard Truth on Family, Kids and Money'' (2015) * ''Digital Pivot or Bust In a Post COVID-19 World: Why Small Businesses Must Re-Think Everything to Survive and Thrive!'' (2020)


Media


''Dragons' Den'' and ''Shark Tank''

In 2006, O'Leary appeared as one of the five follow-up venture capitalists on the then-new show ''
Dragons' Den ''Dragons' Den'' is a reality television program format in which entrepreneurs pitch their business ideas to a panel of venture capitalists in the hope of securing investment finance from them. The program originated in 2001 in Japan, where it ...
'' on
CBC CBC may refer to: Media * Cadena Baja California or Grupo Cadena, a radio and television broadcaster in Mexico * Canadian Broadcasting Corporation, Canada's radio and television public broadcaster ** CBC Television ** CBC Radio One ** CBC Music ** ...
, the Canadian installment of the international ''
Dragons' Den ''Dragons' Den'' is a reality television program format in which entrepreneurs pitch their business ideas to a panel of venture capitalists in the hope of securing investment finance from them. The program originated in 2001 in Japan, where it ...
'' format. On the show, O'Leary developed a
persona A persona (plural personae or personas) is a strategic mask of identity in public, the public image of one's personality, the social role that one adopts, or simply a fictional Character (arts), character. It is also considered "an intermediary ...
as a blunt, abrasive 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 occasionally asked O'Leary to be "more evil" during the first two seasons. ''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 ''Shark Tank'' is an American business Reality television#Investments, reality television series that premiered on August 9, 2009, on American Broadcasting Company, ABC.Hibberd, James (May 10, 2012)Dancing,' 'Bachelor,' and a bigger 'Shark Tank ...
'', began, and ''Shark Tank'' executive producer
Mark Burnett James Mark Burnett (born 17 July 1960) is a British television producer who has won thirteen Emmy Awards including ten Primetime, one Sports Emmy Award and two Daytime Emmy Awards. His other accolades include five Producers Guild of America A ...
invited two of the CBC ''Dragons' Den'' investors, O'Leary and
Robert Herjavec Robert Herjavec (; born September 14, 1962) is a Croatian-Canadian businessman, investor, and television personality. Herjavec founded BRAK Systems, a Canadian integrator of Internet security software, and sold it to AT&T Canada (now Allstream ...
, 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 favourite, winning the
Primetime Emmy Award for Outstanding Structured Reality Program The Primetime Emmy Award for Outstanding Structured Reality Program is handed out annually at the Creative Arts Emmy Award ceremony. In 2014, Outstanding Reality Program was separated into two categories – Outstanding Unstructured Reality Pr ...
four 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, naive, and inexperienced 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 acerbic demeanor, domineering imposition, and blunt television persona, O'Leary has 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 Jamba, formerly known as Jamba Juice, is an American quick-service restaurant and juice bar chain that sells blended fruit and vegetable juices, smoothies, and other food products. The first Jamba location, originally named Juice Club, opened ...
) and GrooveBook (later bought by
Shutterfly Shutterfly, LLC. is an American photography, photography products, and image sharing company, headquartered in San Jose, California. The company is mainly known for custom photo printing services, including books featuring user-provided images, ...
), the latter with
Mark Cuban Mark Cuban (born July 31, 1958) is an American businessman and television personality. He is the former principal owner and current minority owner of the Dallas Mavericks of the National Basketball Association (NBA) and co-owner of 2929 Entertain ...
. Some of his recent investments include Hello Prenup with Nirav Tolia of
Nextdoor Nextdoor Holdings, Inc. is an American company that operates a hyperlocal social networking service for neighborhoods. The company was founded in 2008 and is based in San Francisco, California. Nextdoor launched in the United States in October ...
. All of his ''Dragons' Den'' and ''Shark Tank'' investments are consolidated, presided, and managed under his
holding company A holding company is a company whose primary business is holding a controlling interest in the Security (finance), securities of other companies. A holding company usually does not produce goods or services itself. Its purpose is to own Share ...
, called "Something Wonderful."


Discovery Channel's ''Discovery Project Earth''

In 2008, O'Leary worked as a co-host for the
Discovery Channel Discovery Channel, known as The Discovery Channel from 1985 to 1995, and often referred to as simply Discovery, is an American cable channel that is best known for its ongoing reality television shows and promotion of pseudoscience. It init ...
's '' Discovery Project Earth'', a show that explores innovative ways to reverse
climate change Present-day climate change includes both global warming—the ongoing increase in Global surface temperature, global average temperature—and its wider effects on Earth's climate system. Climate variability and change, Climate change in ...
.


The Lang and O'Leary Exchange

In 2009, O'Leary began appearing with journalist
Amanda Lang Amanda Lang (born 31 October 1970) is a Canadian business journalist, and host of ''Taking Stock'', a weekly business news program on CTV, BNN Bloomberg and CP24. Previously, she was the host of ''Bloomberg North'' on Bloomberg TV Canada. La ...
on
CBC News Network CBC News Network (formerly CBC Newsworld) is a Canadian English-language specialty news channel owned by the Canadian Broadcasting Corporation (CBC). It is Canada's first all-news channel, and the world's third-oldest television service of this ...
's ''
The Lang and O'Leary Exchange ''The Exchange'' was a Canadian business news television series which aired weekdays on CBC News Network, with an overnight rebroadcast on CBC Television, from October 26, 2009 to September 9, 2016. The show originally launched as ''The Lang an ...
''. During a segment of ''The Lang & O'Leary Exchange'' on the
Occupy Wall Street Occupy Wall Street (OWS) was a left-wing populist movement against economic inequality, capitalism, corporate greed, big finance, and the influence of money in politics that began in Zuccotti Park, located in New York City's Financial ...
protests in 2011, O'Leary criticized Pulitzer Prize-winning journalist
Chris Hedges Christopher Lynn Hedges (born September 18, 1956) is an American journalist, author, commentator and Presbyterian minister. In his early career, Hedges worked as a freelance war correspondent in Central America for ''The Christian Science Monit ...
for sounding "like a left-wing nutbar." Hedges said afterward that "it will be the last time" he would appear on the show and compared the CBC to
Fox News The Fox News Channel (FNC), commonly known as Fox News, is an American Multinational corporation, multinational Conservatism in the United States, conservative List of news television channels, news and political commentary Television stati ...
. CBC's
ombudsman An ombudsman ( , also ) is a government employee who investigates and tries to resolve complaints, usually through recommendations (binding or not) or mediation. They are usually appointed by the government or by parliament (often with a sign ...
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,


Other projects

In 2009, O'Leary hosted a
Winnipeg Comedy Festival The Winnipeg Comedy Festival (WCF) is an annual national comedy festival, held in Winnipeg, Manitoba. The week-long festival takes place at several venues throughout the city, featuring Stand-up comedy, stand-up, Sketch comedy, sketch, and improvis ...
gala called ''Savings & Groans'' in which he performed a ''Dragon's Den'' style sketch in which
Sean Cullen Sean, also spelled Seán or Séan in Hiberno-English, is a male given name of Irish origin. It comes from the Irish versions of the Biblical Hebrew name ''Yohanan'' (), Seán (anglicized as '' Shaun/ Shawn/ Shon'') and Séan (Ulster variant; ang ...
and Ron Sparks tried to get him to invest in their invention - the wheel. The show aired on
CBC CBC may refer to: Media * Cadena Baja California or Grupo Cadena, a radio and television broadcaster in Mexico * Canadian Broadcasting Corporation, Canada's radio and television public broadcaster ** CBC Television ** CBC Radio One ** CBC Music ** ...
in 2010. O'Leary co-produced and hosted the 2012 reality show '' Redemption Inc.'', which aired for one season on CBC, in which ten ex-convicts competed to have O'Leary fund their business idea. Having also been a co-host of ''SqueezePlay'' on
Bell Media Bell Media Inc. (Canadian French, French: ) is a Canadian media conglomerate that is the mass media subsidiary of BCE Inc. (also known as Bell Canada Enterprises, the owner of telecommunications company Bell Canada). Its operations include nati ...
's
Business News Network BNN Bloomberg is a Canadian English language discretionary specialty channel owned by Bell Media with the name licensed from Bloomberg L.P. It broadcasts programming related to business and financial news and analysis. The channel is headquarte ...
(BNN), he returned to the Discovery Channel on September 1, 2014, to join as a contributor for its radio and television stations such as CTV. On May 5, 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 that year, O'Leary appeared as a celebrity judge in the 95th
Miss America Miss America is an annual competition that is open to women from the United States between the ages of 18 and 28. Originating in 1921 as a "bathing beauty revue", the contest is judged on competition segments with scoring percentages: ''Priva ...
pageant. In 2018 O'Leary hosted the podcast ''Ask Mr. Wonderful'' for seven episodes. In 2019, he began posting videos on
YouTube YouTube is an American social media and online video sharing platform owned by Google. YouTube was founded on February 14, 2005, by Steve Chen, Chad Hurley, and Jawed Karim who were three former employees of PayPal. Headquartered in ...
, again under the title "Ask Mr. Wonderful". In 2021, O'Leary appeared with Katie Phang and Ada Pozo on
CNBC CNBC is an American List of business news channels, business news channel owned by the NBCUniversal News Group, a unit of Comcast's NBCUniversal. The network broadcasts live business news and analysis programming during the morning, Day ...
's ''Money Court'', where they adjudicated financial disputes. He is currently a member of ARHT Media's Board of Advisors. He has an acting role in the upcoming 2025 movie '' Marty Supreme''.


Political activity

In January 2016, O'Leary offered to invest $1 million in the economy of
Alberta Alberta is a Provinces and territories of Canada, province in Canada. It is a part of Western Canada and is one of the three Canadian Prairies, prairie provinces. Alberta is bordered by British Columbia to its west, Saskatchewan to its east, t ...
in exchange for the resignation of
Premier Premier is a title for the head of government in central governments, state governments and local governments of some countries. A second in command to a premier is designated as a deputy premier. A premier will normally be a head of govern ...
Rachel Notley Rachel Anne Notley (born April 17, 1964) is a Canadian lawyer and former politician who was the 17th premier of Alberta from 2015 to 2019 and leader of the Alberta New Democratic Party (NDP) from 2014 to 2024. Notley was the member of the Le ...
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 of economic collapse.


2017 federal Conservative Party leadership race

Following
Stephen Harper Stephen Joseph Harper (born April 30, 1959) is a Canadian politician who served as the 22nd prime minister of Canada from 2006 to 2015. He is to date the only prime minister to have come from the modern-day Conservative Party of Canada, ser ...
's resignation as leader of the
Conservative Party of Canada The Conservative Party of Canada (CPC; , ), sometimes referred to as the Tories, is a Government of Canada, federal List of political parties in Canada, political party in Canada. It was formed in 2003 by the merger of the two main Right-wing ...
, O'Leary attended Conservative Party gatherings in February and May 2016, leading to public speculation about whether he would run for the 2017 leadership election. In February 2016,
Maxime Bernier Maxime Bernier (; born January 18, 1963) is a Canadian politician who is the founder and leader of the People's Party of Canada (PPC). Formerly a member of the Conservative Party of Canada, Conservative Party, Bernier left the caucus in 2018 t ...
, 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 Lisa Sarah MacCormack Raitt (born May 7, 1968) is a former Canadian politician who served as a federal Cabinet minister and member of Parliament (MP) from 2008 to 2019. A member of the Conservative Party, Raitt was elected to the House of Com ...
, who was trying to improve her French. O'Leary stated that he was taking French lessons, and he promised to learn French in time for the next federal election. On January 18, 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 February 1, 2017, O'Leary posted a video of himself shooting in a
Miami Miami is a East Coast of the United States, coastal city in the U.S. state of Florida and the county seat of Miami-Dade County, Florida, Miami-Dade County in South Florida. It is the core of the Miami metropolitan area, which, with a populat ...
gun range. It was removed from
Facebook Facebook is a social media and social networking service owned by the American technology conglomerate Meta Platforms, Meta. Created in 2004 by Mark Zuckerberg with four other Harvard College students and roommates, Eduardo Saverin, Andre ...
out of respect for the funeral for three victims of the
Quebec City mosque shooting The Quebec City mosque shooting () was an attack by a single gunman on the evening of January 29, 2017, at the Islamic Cultural Centre of Quebec City, a mosque in the Sainte-Foy, Quebec City, Sainte-Foy neighbourhood of Quebec City, Canada. S ...
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. 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 in Quebec meant that it would be difficult for him to beat Trudeau in 2019, and it would thus be "selfish" of him to continue. On dropping out, he endorsed Bernier, another frontrunner for the position. (
Andrew Scheer Andrew James Scheer (born May 20, 1979) is a Canadian politician who is the Leader of the Official Opposition (Canada), leader of the Opposition since 2025 and previously from 2017 to 2020 as Leader of the Conservative Party (Canada), leader of ...
eventually won the leadership election, narrowly edging out Bernier.)


Political positions


Donald Trump support

In 2017, O'Leary described hypothetical trade negotiations between US President
Donald Trump Donald John Trump (born June 14, 1946) is an American politician, media personality, and businessman who is the 47th president of the United States. A member of the Republican Party (United States), Republican Party, he served as the 45 ...
and Canadian Prime Minister
Justin Trudeau Justin Pierre James Trudeau (born December 25, 1971) is a Canadian politician who served as the 23rd prime minister of Canada from 2015 to 2025. He led the Liberal Party from 2013 until his resignation in 2025 and was the member of Parliament ...
as "
Godzilla is a fictional monster, or ''kaiju'', that debuted in the eponymous 1954 film, directed and co-written by Ishirō Honda. The character has since become an international pop culture icon, appearing in various media: 33 Japanese films p ...
versus
Bambi ''Bambi'' is a 1942 American Animated film, animated Coming of age, coming-of-age drama film produced by Walt Disney Productions and released by RKO Radio Pictures. Loosely based on Felix Salten's 1923 novel ''Bambi, a Life in the Woods'', the ...
". During the U.S. presidential election of 2024, O'Leary criticized Democratic presidential candidate Kamala Harris, citing her plan to increase corporate taxes. During the campaign, O'Leary also 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. Amid President
Donald Trump Donald John Trump (born June 14, 1946) is an American politician, media personality, and businessman who is the 47th president of the United States. A member of the Republican Party (United States), Republican Party, he served as the 45 ...
's threats in 2025 to impose 25% tariffs on Canadian goods and annex Canada, O'Leary visited Trump at his Mar-a-Lago resort. O'Leary also supported making Canada part of the United States and said, "Think about the power of combining the two economies."


Economy and trade

O'Leary supports multilateral free trade agreements such as the
North American Free Trade Agreement The North American Free Trade Agreement (, TLCAN; , ALÉNA), referred to colloquially in the Anglosphere as NAFTA, ( ) was an agreement signed by Canada, Mexico, and the United States that created a trilateral trade bloc in North America. The ...
. O'Leary believes corporate tax rates in Canada are too high and has promised to eliminate the national
carbon tax A carbon tax is a tax levied on the carbon emissions from producing goods and services. Carbon taxes are intended to make visible the hidden Social cost of carbon, social costs of carbon emissions. They are designed to reduce greenhouse gas emis ...
. O'Leary has threatened to punish
provinces A province is an administrative division within a country or state. The term derives from the ancient Roman , which was the major territorial and administrative unit of the Roman Empire's territorial possessions outside Italy. The term ''provi ...
by withholding transfer payments if they do not eliminate their respective carbon taxes. O'Leary is a critic of
deficit spending Within the budgetary process, deficit spending is the amount by which spending exceeds revenue over a particular period of time, also called simply deficit, or budget deficit, the opposite of budget surplus. The term may be applied to the budg ...
and supports eliminating the
national debt A country's gross government debt (also called public debt or sovereign debt) is the financial liabilities of the government sector. Changes in government debt over time reflect primarily borrowing due to past government deficits. A deficit occ ...
. O'Leary opposes control of the
CRTC The Canadian Radio-television and Telecommunications Commission (CRTC; ) is a public organization in Canada tasked with the mandate as a regulatory agency tribunal for various electronic communications, covering broadcasting and telecommunic ...
over Canada's telecommunications system. He has accused Rep.
Alexandria Ocasio-Cortez Alexandria Ocasio-Cortez (born October 13, 1989), also known as AOC, is an American politician and activist who has served since 2019 as the United States House of Representatives, US representative for New York's 14th congressional distric ...
, a New York politician, of "killing jobs by the thousands," citing higher corporate taxes which she favors. O'Leary supports the
Trump administration Presidency of Donald Trump may refer to: * First presidency of Donald Trump, the United States presidential administration from 2017 to 2021 * Second presidency of Donald Trump, the United States presidential administration since 2025 See also * ...
's
Liberation Day tariffs On April 2, 2025, United States president Donald Trump held a White House Rose Garden ceremony where he announced what he called a " reciprocal tariff" strategy, which he had previously promised and described as necessary to correct what he ch ...
policy and has called for increasing United States' tariffs on
China China, officially the People's Republic of China (PRC), is a country in East Asia. With population of China, a population exceeding 1.4 billion, it is the list of countries by population (United Nations), second-most populous country after ...
to 400%.


Labor rights

O'Leary opposes right to disconnect legislation, which gives employees the legal right not to respond to work-related communications outside of working hours.


Energy

O'Leary supports building a pipeline from the
Athabasca oil sands The Athabasca oil sands, also known as the Athabasca tar sands, are large deposits of oil sands rich in bitumen, a heavy and viscous form of petroleum, in northeastern Alberta, Canada. These reserves are one of the largest sources of unconventi ...
to
Eastern Canada Eastern Canada (, also the Eastern provinces, Canadian East or the East) is generally considered to be the region of Canada south of Hudson Bay/ Hudson Strait and east of Manitoba, consisting of the following provinces (from east to west): Newf ...
with the intention 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.


Social

O'Leary describes his social policies as "very liberal". He supports
same-sex marriage Same-sex marriage, also known as gay marriage, is the marriage of two people of the same legal Legal sex and gender, sex. marriage between same-sex couples is legally performed and recognized in 38 countries, with a total population of 1.5 ...
and
transgender A transgender (often shortened to trans) person has a gender identity different from that typically associated with the sex they were sex assignment, assigned at birth. The opposite of ''transgender'' is ''cisgender'', which describes perso ...
rights. O'Leary supports the legalization and regulation of
marijuana Cannabis (), commonly known as marijuana (), weed, pot, and ganja, List of slang names for cannabis, among other names, is a non-chemically uniform psychoactive drug from the ''Cannabis'' plant. Native to Central or South Asia, cannabis has ...
. O'Leary supports
assisted suicide Assisted suicide, sometimes restricted to the context of physician-assisted suicide (PAS), is the process by which a person, with the help of others, takes actions to end their life. Once it is determined that the person's situation qualifie ...
and cited Switzerland as a model for Canada to follow.


Foreign and military policy

O'Leary supported ending Canadian airstrikes on ISIS and supports taking a peacekeeping role in the Syrian Civil War. In 2017, O'Leary described Russia as "neither an ally nor a foe" in an interview with the CBC. O'Leary has criticized
Justin Trudeau Justin Pierre James Trudeau (born December 25, 1971) is a Canadian politician who served as the 23rd prime minister of Canada from 2015 to 2025. He led the Liberal Party from 2013 until his resignation in 2025 and was the member of Parliament ...
's procurement plan. He supports purchasing aerial combat drones to defend
Canadian airspace file:Canadian_CF-18_Hornet_escorts_Soviet_Tupolev_Tu-95_in_1987.jpg, 300px, Canadian CF-18 escorts Soviet Tu-95 bomber, 1987 Canadian airspace is the region of airspace above the surface of the Earth within which Canada has jurisdiction. It falls wi ...
and supports phasing out the use of the
Lockheed CP-140 Aurora The Lockheed CP-140 Aurora is a maritime patrol aircraft operated by the Royal Canadian Air Force. The aircraft is based on the Lockheed P-3 Orion airframe, but mounts the electronics suite of the Lockheed S-3 Viking. "Aurora" refers to the R ...
citing cost reasons. He has criticized the lack of funding of the
Canadian Armed Forces The Canadian Armed Forces (CAF; , FAC) are the unified Military, military forces of Canada, including sea, land, and air commands referred to as the Royal Canadian Navy, Canadian Army and the Royal Canadian Air Force. Under the ''National Defenc ...
and supports spending the
NATO The North Atlantic Treaty Organization (NATO ; , OTAN), also called the North Atlantic Alliance, is an intergovernmental organization, intergovernmental Transnationalism, transnational military alliance of 32 Member states of NATO, member s ...
recommended 2% of GDP on military expenditures.


Immigration

O'Leary has proposed creating a "fast track" for citizenship for immigrants who graduate from college or university and find employment, as well as for their spouses and children. O'Leary has advocated for increased border security in order to tackle the issue of irregular border crossing.


Senate

In a 2017 interview with
Evan Solomon Evan Solomon (born April 20, 1968) is a Canadian politician and broadcaster who has been the minister of artificial intelligence and digital innovation since May 2025. A member of the Liberal Party, Solomon was elected as the member of Parliam ...
, 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 Elections Canada () is the non-partisan agency responsible for administering elections in Canada, Canadian federal elections and Referendums in Canada, referendums. History Elections Canada is an agency of the Parliament of Canada, and reports ...
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 publicly stated that the law promoted mediocrity since rich people would be discouraged from running and hurt the businesses that 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 Charter right to security of the person.


Personal life

O'Leary is
Catholic The Catholic Church (), also known as the Roman Catholic Church, is the List of Christian denominations by number of members, largest Christian church, with 1.27 to 1.41 billion baptized Catholics Catholic Church by country, worldwid ...
. He and his wife, Linda (
née The birth name is the name of the person given upon their birth. The term may be applied to the surname, the given name or to the entire name. Where births are required to be officially registered, the entire name entered onto a births registe ...
Greer), have been married since 1990. The couple separated in 2011, but they resumed their marriage after two years. They have two children, Trevor and Savannah. In a 2016 interview, 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." The O'Learys live in
Miami Beach Miami Beach is a coastal resort city in Miami-Dade County, Florida, United States. It is part of the Miami metropolitan area of South Florida. The municipality is located on natural and human-made barrier islands between the Atlantic Ocean an ...
and
Toronto Toronto ( , locally pronounced or ) is the List of the largest municipalities in Canada by population, most populous city in Canada. It is the capital city of the Provinces and territories of Canada, Canadian province of Ontario. With a p ...
. He also maintains a cottage in Muskoka, Ontario, as well as homes in
Boston Boston is the capital and most populous city in the Commonwealth (U.S. state), Commonwealth of Massachusetts in the United States. The city serves as the cultural and Financial centre, financial center of New England, a region of the Northeas ...
and
Geneva Geneva ( , ; ) ; ; . is the List of cities in Switzerland, second-most populous city in Switzerland and the most populous in French-speaking Romandy. Situated in the southwest of the country, where the Rhône exits Lake Geneva, it is the ca ...
, Switzerland. In a 2022 CNBC interview, he mentioned that he has obtained a
United Arab Emirates The United Arab Emirates (UAE), or simply the Emirates, is a country in West Asia, in the Middle East, at the eastern end of the Arabian Peninsula. It is a Federal monarchy, federal elective monarchy made up of Emirates of the United Arab E ...
citizenship in order to be able to partner with
Emiratis The Emiratis (; ) are the Citizenship, citizen population of the United Arab Emirates. Within the UAE itself, their number is approximately 1.15 million. Formerly known as the Trucial States, the UAE is made up of Emirates of the United Arab E ...
on investments. O'Leary is a fan of the
New England Patriots The New England Patriots are a professional American football team based in the Greater Boston area. The Patriots compete in the National Football League (NFL) as a member of the American Football Conference (AFC) AFC East, East division. The Pa ...
football team and claims to watch all of their games, even when he is traveling around the world and games occur during the middle of the night. He is a wine aficionado and belongs to the
Confrérie des Chevaliers du Tastevin The ''Confrérie des Chevaliers du Tastevin'' (literally "Fraternity of the Knights of the Wine-Tasting Cup") is a Bacchanalian fraternity of wine connoisseurs established in 1934 to promote Burgundian wines and culture. Originally formed und ...
, an international association of
Burgundy wine Burgundy wine ( or ') is made in the Burgundy region of eastern France, in the valleys and slopes west of the Saône, a tributary of the Rhône. The most famous wines produced here, and those commonly referred to as "Burgundies", are dry (wine), ...
enthusiasts. He is also a lifelong photographer and has exhibited and sold prints of his photographs, donating the proceeds to charity. O'Leary is also an avid watch collector and expert, sharing his insights on both ''Shark Tank'' and social media.


Boating accident

On August 24, 2019, O'Leary and his wife Linda were involved in a fatal crash on
Lake Joseph Lake Joseph is located in Seguin Township, Ontario Ontario is the southernmost Provinces and territories of Canada, province of Canada. Located in Central Canada, Ontario is the Population of Canada by province and territory, country's mos ...
in Muskoka, Ontario, when they were on a boat owned by O'Leary and allegedly operated at the time by Linda. The O'Learys' boat collided with another one and a 64-year-old man and 48-year-old woman on that vessel were killed. O'Leary said in a statement that he was cooperating with the police investigation 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 was charged with "careless operation of a vessel" under the small vessel regulations of the ''
Canada Shipping Act The ''Canada Shipping Act'' () is legislation enacted by the Parliament of Canada, governing the powers of government to regulate the registration and operation of ships and pleasure craft, including personnel and navigation. The Act also estab ...
'', a charge that carries maximum 18 months imprisonment and a $10,000 fine. The driver of the other boat, Richard Ruh of
Orchard Park, New York Orchard Park is an incorporated Administrative divisions of New York#Town, town in Erie County, New York, United States. It is an outer ring suburb southeast of Buffalo, New York, Buffalo. As of the 2010 United States census, 2010 census, the po ...
, was charged with "failing to exhibit navigation light while underway". On October 11, the Public Prosecution Service of Canada ruled out jail time for Linda. On September 14, 2021, Linda was found not guilty of careless operation of the vessel.


See also

*
List of University of Waterloo people The University of Waterloo, located in Waterloo, Ontario, Canada, is a comprehensive public university that was founded in 1957 by Drs. Gerry Hagey and Ira G. Needles. It has grown into an institution of more than 42,000 students, faculty, and st ...


References


External links

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