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O'Leary in 2012
|Born||Terence Thomas Kevin O'Leary
9 July 1954
Montreal, Quebec, Canada
|Other names||Mr. Wonderful|
|Alma mater||University of Waterloo
University of Western Ontario
|Net worth||US$400 Million+|
|Spouse(s)||Linda O'Leary (m. 1990)|
|Children||Trevor and Lauren O'Leary|
Terence Thomas Kevin O'Leary (born 9 July 1954) is a Canadian businessman, investor, writer, financial commentator, and television and radio personality. He is co-founder and chairman of O'Leary Funds and the co-founder of SoftKey. He previously served as a commentator on Canada's CBC Television and CBC News Network programme The Lang and O'Leary Exchange and hosted Redemption Inc. He is an investor on the ABC reality television series Shark Tank and was a venture capitalist "Dragon" on CBC Television's Dragons' Den.
Initially aspiring to become a photographer, O'Leary developed an interest in business and investing at a young age watching his mother invest her weekly paycheque into various stocks and bonds. He holds an honours bachelor's degree from the University of Waterloo in Ontario and an MBA from the University of Western Ontario.
O'Leary began his career in the early 1980s as an assistant brand manager for Nabisco, where he increased market share for Nabisco's biggest cat food brand. He later went on to co-found Special Event Television, a moderately successful television production company that produced original sports programming such as "The Original Six," "Don Cherry's Grapevine" and "Bobby Orr and the Hockey Legends."
In 1986, 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. The company developed educational, reference and home-productivity software, garnering annual sales of more than $800 million, with 2,000 employees and subsidiaries in 15 countries. SoftKey later changed its name to The Learning Company and was acquired by The Mattel Toy Company in 1999, with the sale making O'Leary a multimillionaire.
Early life and education
O'Leary was born in Montreal, Quebec, Canada, the son of Georgette (née Bukalam), a small-business owner and investor, and Terry O'Leary, a salesman. His father was Irish, and his mother was of Lebanese descent.
O'Leary's parents divorced when he was a child, and his father died shortly thereafter. After his father's death, O'Leary's mother ran the business as an executive. His mother later married an economist 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 Quebec schools Stanstead College and St. George's School.
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 best-selling 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 his 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 a moderately successful, 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 the company, O'Leary moved on to his second business venture, Softkey, 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 desperate for funding to support the fledgling business. He credits this experience with teaching him the critical lesson of always having more than one source of financing available when starting a new business. He used the proceeds from the sale of his share of Special Event Television and convinced his mother to lend him $10,000 in seed capital to establish SoftKey Software Products. He launched Softkey in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock.
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 was able to develop a number of educational software products focused primarily 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. This success allowed O'Leary to abandon his initial distribution strategy and for something more cost-effective: licensing software and marketing it under the SoftKey brand.
Softkey weathered stiff competition from other software companies in the late 1980s and prospered throughout the 1990s. O'Leary was an aggressive promoter of the company's products and gained a reputation for aggressively and single-mindedly pursuing market share. Softkey eventually acquired its major competitors and scrapped products in their software portfolios that didn't sell. By 1994, 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. Softkey International moved its headquarters to Cambridge, Massachusetts, and changed its name to The Learning Company.
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, and in 1999, TLC and its 467 software titles were acquired by Mattel for $4.2 billion USD. Mattel planned to leverage The Learning Company's interactive software to take Barbie, Hot Wheels and other iconic brands into the interactive world and develop new revenue streams. O'Leary sold the company in 1999 to Mattel. 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 history. Following the acquisition, Mattel experienced a USD$105 million loss where management had projected a US$50-million profit. Mattel's stock crashed, wiping out USD$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 in 2003. O'Leary primarily blamed the financial meltdown on the culture clash between the two companies.
Later, 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 Storage Now, Canada's leading developer of climate-controlled storage facilities. O'Leary learned of the opportunity through Toronto entrepreneur Reza Satchu, and invested $500,000 for a 13% equity in the business. Storage Now became the third-largest owner and operator of storage services in Canada, with facilities in 11 cities and was acquired by In Storage REIT in March 2007 for $110 million. O'Leary sold his shares, originally worth $500,000, for more than $4.5 million. In May 2005, REza and O'Leary's partner, filed a $10-million wrongful-dismissal lawsuit against them, charging that they had altered an agreed-upon compensation deal and reduced Wheeler's share of the profits.
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 he 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. O'Leary described his investment objectives for the fund with two ideas: yield and capital preservation. The fund utilizes O'Leary's value-yield style of investing, and the fund has seen its assets under management grow from $400 million in 2011 to $1.2-billion in 2012. The fund's primary manager is Stanton Asset Management, a firm controlled by the husband-and-wife team of Connor O'Brien and Louise Ann Poirier. O’Brien, an ex-Wall Street money manager born in Montreal, had worked for Merrill Lynch and Lehman Brothers, and started a private-equity investing firm, Stanton Capital Corp, in 1995. 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.
When investing in TSX stocks, O'Leary usually focuses on companies that have nothing associated with oil and gas and companies that generate more than 50 percent of their revenues in the United States. When the Canadian economy fell into a technical recession in early 2015, he advised investors to continue to place their money into Canadian equities, despite the pessimism of many economists. O'Leary has also been an active investor in Asia, particularly China, since 2013. He continues to remain bullish on the growth of the Chinese economy and stock market, despite a sell-off by Chinese investors in late July 2015.
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, and gives advice to budding entrepreneurs. 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 great wealth. Money management techniques, common money mistakes, and developing financial freedom are each targeted toward a specific stage in a person's life. 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.
O'Leary is a former co-host of SqueezePlay on Business News Network (BNN), Canada's national business television channel. He worked as a co-host for the Discovery Channel's Discovery Project Earth, a show that explores innovative ways to reverse climate change. Even so, O'leary has often said that he doesn't "buy" that sea levels are already rising and some weather-related events or becoming more severe. He has said that to "do it right" the world should continue to study climate change for "50 to 100 years ... In 100 years from now, then we can put a carbon tax on, if in fact it stays in place."
O'Leary served as foil to journalist Amanda Lang on CBC News Network's The Lang and O'Leary Exchange, and he appeared as a venture capitalist on the Canadian television show Dragons' Den until departing CBC in late 2014. Since 2009 he has been a shark on the American version of Dragons' Den, Shark Tank, which airs on ABC. During his time on the two reality shows, he acquired the nickname "Mr. Wonderful". He became well-known on both shows for computing financial valuations mentally while negotiating offers with the contestants. He also produced and hosted his own reality show, Redemption Inc., in which he tries to help ex-convicts start and develop their own businesses.
During a segment of The Lang & O'Leary Exchangeon 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 on reports that the world's richest 85 people owned as much wealth as the bottom half of the population was "fantastic news".
|“||It's fantastic, and this is a great thing because it inspires everybody, gets them motivation to look up to the one percent and say, 'I want to become one of those people, I'm going to fight hard to get up to the top.' This is fantastic news, and, of course, I applaud it. What can be wrong with this? I celebrate capitalism. Don't tell me that you want to redistribute wealth again, that's never gonna happen ... it's a celebratory stat. ... If you work hard, you might be stinking rich one day.||”|
In 2014 O'Leary left Dragon's Den after eight seasons to focus more on his role on Shark Tank. On 1 September 2014, it was announced that O'Leary had joined Bell Media, where he would return to BNN, serve as a contributor for CTV programs, and be a financial commentator for Bell Media news radio stations.
Business ventures and investments
Following his business ventures in software, storage facilities and private equity, O'Leary moved into investing, winemaking and mortgages. His ventures included O'Leary Funds (a mutual and investment fund management firm that handles more than $1.5 billion), O'Leary Ventures (a private early-stage venture capital investment company that invests in and partners with early-stage, high-growth-potential companies in various Canadian industries), O'Leary Mortgages (a mortgage firm), O'Leary books, and O'Leary Fine Wines (a winemaking company). In April 2014, O'Leary Mortgages went out of business.
On 14 July 2015, O'Leary launched his own ETF through O'Shares Investments, a division of his investment fund, O'Leary Funds Management LP, where O'Leary serves as the Chairman. O’Leary began to grow O’Shares Investments by offering non-cash compensation to registered investment advisors who purchase his products. The non-cash compensation was in the form of a "Kevin O’Leary speaking engagement", which was given a monetary value of $40,000. O’Leary has faced penalties in the past from securities regulators.
O'Leary has 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 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. He also has a strong preference for stocks that pay dividends. He keeps 50 percent of his family trusts in equities while the other half is concentrated in credits and bonds. He says he likes investments that earn money while he sleeps and views his investment portfolio as like a "chicken on a spit dripping cash".
In January 2016, O'Leary expressed interest in running in the upcoming leadership election of the Conservative Party of Canada, saying that he had been inspired by Donald Trump's campaign for President of the United States. O'Leary created controversy by offering to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley. He appeared with four other prospective leadership candidates at a conference for federal Conservatives in late February 2016 and gave a presentation titled "If I Run, This is How." During this speech he predicted that the Liberal government would fall within four years as a result of economic collapse. Politically, he sees himself as mainly focused on the economy and as an opponent of government waste, high taxes and a low Canadian dollar. Maxime Bernier, a Quebecois Conservative politician, attacked Kevin O'Leary for his statements, calling him a "tourist" for not being able to speak French and wanting to be Prime Minister. Bernier later clarified his comments by explaining that he wanted all leadership candidates to learn French by praising his fellow leadership contender Lisa Raitt, who was struggling to learn French. Chantal Hébert says that a non-Francophone campaign would likely fail at forming the government giving the current political climate. O'Leary has been compared to Donald Trump based on their personality traits; however political commentators have questioned his temperament because his path to Prime Minister is more grueling than Trump. Since he currently lives in Boston, he has been compared to Michael Ignatieff, who was attacked by Conservative Party for living outside of Canada for a long period of time. 
O'Leary became a member of the Conservative Party shortly before the party's 2016 convention. In December 2016, O'Leary revealed an exploratory committee that included former premier of Ontario, Mike Harris.
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.
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