Kevin O'Leary

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Kevin O'Leary
Born Terence Thomas Kevin O'Leary[1]
(1954-07-09) 9 July 1954 (age 61)
Montreal, Quebec, Canada
Nationality Canadian
Alma mater University of Waterloo
University of Western Ontario
Occupation Founder of SoftKey
Co-investor and Director of Storage Now
Co-founder and Chairman of O'Leary Funds
Co-investor and Venture capitalist in Dragons' Den and Shark Tank
Former Co-host of The Lang and O'Leary Exchange
Author of the Cold Hard Truth
Years active 1979 - present
Net worth Increase US$300 million[2][3]
Children Trevor & Savannah O'Leary
Website Official website

Terence "Kevin" Thomas O'Leary (born 9 July 1954) is a Canadian businessman, investor, journalist, writer, financial commentator and television personality. O'Leary is one Canada's most prominent entrepreneurs. He is most recognized as a tough "Shark" investor on the ABC reality television series Shark Tank as well as a venture capitalist "Dragon" on CBC's Dragons' Den. As an investor and venture capitalist on both CBC’s Dragon’s Den and ABC’s Shark Tank , O'Leary is known for his ruthless demeanor, realist attitude, blunt and brutal honesty and controversial comments, including insults and wisecracks about contestants pitches and their products, services, business savvy, and entrepreneurial abilities.

Early life and education[edit]

O'Leary was born in Montreal, Canada to a Canadian father of Irish origin who worked as a salesman and a Canadian mother of Lebanese origin who was a small businesswoman and investor that initially worked as a seamstress. Business has long ran in his family's bloodline, with his mother Georgette of Lebanese origin with distant Phoenician ancestry is descended from a long line of successful Lebanese businessmen and trade merchants.[4][5][6][7] O'Leary's maternal grandfather, Joseph Bookalam immigrated to Canada in 1904 from a small village in Lebanon at the age of 16. Bookalam had an uncle who was a general store owner and worked at the store for three straight years handling inventory and serving customers where he eventually saved enough money that provided enough seed capital to buy a horse and sleigh in order to launch his career as a roving salesman. Bookalam later married O'Leary's maternal grandmother Akaber, who was coincidentally from the same village that Joseph came from and had four children. Bookalam later moved to Montreal and amassed substantial savings from his career as a roving salesman and used his savings as the startup capital to establish Kiddie Togs, a factory which made high end children's winter clothing.[5]

His mother, Georgette ran the business for a time when working as a seamstress. O'Leary's parents divorced when he was a child and his father died shortly thereafter. As a result of a broken marriage, O'Leary witnessed his mother stagger under the emotional and financial problems and his mother later remarried an economist of Egyptian origin who worked with the UN’s International Labour Organization.[6][8][9] While growing up he lived in several countries, moving around every couple of years.[10] He attended Stanstead College[11] and St. George's School.[12]

O'Leary developed an interest in business and investing at a young age and cites his mother, Georgette, with endowing his interest and facility for business. Despite his mother being a seamstress, Georgette was a seasoned investor, investing a third of her weekly paycheck into large cap dividend paying stocks and interest bearing bonds, ultimately achieving high end returns in her investment portfolio. Since Georgette kept her investment portfolio a secret, O'Leary only discovered this as executor of her estate after she died.[13] One of the earliest lessons O'Leary learned in investing was when he was a young boy and his mother would always tell him to "never spend the principal only the dividends." This lesson eventually later laid the backbone of his mutual fund company, O'Leary Funds.[13]

At Nepean High School in Ottawa, O'Leary was a member of the photo club and brought himself a Soviet Zenit camera and began to develop his own photos.[8] He also worked odd jobs after school to supplement his income, one of which involved washing trucks and working at an ice cream shop.[14] While working at a Magoo's Ice Cream Parlour he engaged in a life changing experience. During his second day of work, the store owner commanded Kevin to get down on his knees and scrape the gum off the floor. His response was "No", at which point she instantly terminated his employment and told him to "get out of her ice cream parlour". Kevin states that he did not even know what the word "fired" meant. Minutes later he was on his bicycle on his way home ashamed and in shock that someone else could have that kind of control over him. O'Leary has stated that the impact of this experience still guides him in his business decisions to date. Since then he has been self-employed.[15] After graduating, he studied for two years at the Royal Military College Saint-Jean.[16]

After graduating from high school, O'Leary aspired to become a photographer. However, advice step-father that being a photographer was not a financially viable and unstable career path to make a sufficient living as only a small percentage of photographers achieve fame and fortune. Taking a reality check and refocusing his career options, he was unwilling to take the risk of taking a second job to support his dreams. O'Leary then put his artistic aspirations on hold to attend university instead at the insistence of his father.[8] O'Leary took his fathers advice by going to university and continued to develop an interest in business and investing.[17] He attended the University of Waterloo where he received an honours bachelor's degree in environmental studies and anthropology.[18] He earned an MBA from the Ivey Business School at The University of Western Ontario.[19] At Ivey, O'Leary had set upon his future sights to become a successful entrepreneur. He convinced the professors to let him do a documentary about the MBA program, and shot the experience for 24 months which later became his thesis.[20]


In 1979, between the first and second years his MBA program, O'Leary applied to a number of companies for a summer placement. He was then picked for a four-month stint at Nabisco, a food conglomerate headquartered in downtown Toronto. Kevin worked briefly as an assistant brand manager at Nabisco Brands selling cat food after earning the position from a summer internship as a young MBA student where his main task was to increase market share for Nabisco's biggest cat food brand.[21][22][23][24]

After leaving Nabisco, O'Leary began his brief career as a television producer before venturing into the software business. With two friends, he co-founded Special Event Television (SET), 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 met limited success producing minor television shows, soccer films, sports vignettes for Hockey Night in Canada and in-between-period commercials for local professional hockey games.[25][26][27][28][22] His ownership was later bought out for $25,000 by one of his partners.[29]

After selling his share of the company, he used the $25,000 proceed earned from selling the television production company and a $10,000 loan from his mother, he co-founded SoftKey Software Products in a Toronto basement in 1986 along with partners John Freeman and Gary Babcock.[28] O'Leary heard about the product in 1983 shortly after meeting a computer programmer who was a member of a users group that designed a graphics program.[30] He immediately jumped at the opportunity to turn the program into a viable business product. To obtain distribution, O'Leary approached printer manufacturers about bundling the program with their hardware as a package. The gambit worked, and the company developed many educational software products, primarily focused on mathematics and reading. Softkey products typically consisted of software intended for home audiences, especially compilation discs containing various freeware or shareware game software packaged in a "jewel-case" CD-ROM.[31][32] Due to this success, O’Leary abandoned the distribution strategy and turned to something more cost-effective, which was licensing software and marketing it under the SoftKey brand. Softkey faced many financial adversities in the late 1980's due to competition from other software companies, but continued to prosper throughout the 1990's, when O'Leary became an aggressive promoter of the company's products. He garnered a reputation for being fanatical about the company's control of the market share through reading market share data and became belligerent if the company even slipped a single share point in one category. O'Leary's fierce drive, brutally blunt and demanding demeanor resulted Softkey wiping out competitors via numerous acquisitions and was ruthless scrapping products in the portfolio that didn't sell. By 1994, Softkey had become a major consolidator in the educational software market, acquiring no fewer than 60 rivals, such as WordStar and Spinnaker Software. In 1995, Softkey acquired The Learning Company (TLC) for $606 million, moved its headquarters to Boston, and took The Learning Company as its name.

The company was moderately profitable throughout the late 1990's where in 1998, it earned more than 800 million USD in 1998 alone despite recording a loss $105 million USD and a loss over the two previous years.[4] TLC bought its former rival Brøderbund in June 1998 for $416 million. In 1999, TLC and its 467 software titles were acquired by Mattel in a $3.8 billion stock swap.[33] O'Leary later sold the company in 1999, for 4.2 billion USD to Mattel.[28] Sales and earnings for Mattel soon dropped, and O'Leary departed from Mattel and received $5 million in severance pay. The purchase by Mattel was later called one of the most disastrous acquisitions in history.[34] Though O’Leary had signed a contract to stay with Mattel for three years, six months after the deal closed, O'Leary was fired. He left with more than US$5 million in severance pay. Following the acquisition, Mattel experienced dismal results were exacerbated by $105 million USD loss where management had projected a US$50-million profit and later Mattel’s stock crashed, wiping out US$3 billion of shareholder value in a single day. Mattel's shareholders later filed a class-action lawsuit accusing Mattel execs, O’Leary and former TLC CEO Michael Perik of misleading investors about the health of TLC and the benefits of the acquisition to Mattel. The lawsuit alleged TLC used accounting tricks to hide losses and inflate quarterly revenue. O'Leary and his defendants disputed all of the charges, and none of the allegations were proven in court. Mattel paid US$122 million to settle in 2003. O'Leary later blamed the financial meltdown primarily on the culture clash between the two companies.[4]

After moving from Softkey, O'Leary went back into the business world where some of his first forays lead to some financial misfortunes. Along with backers from Citigroup, O'Leary to purchase the video game company Atari, which was unsuccessful. At the same time, O'Leary attempted unsuccessfully tried to start a TV video-gaming channel, which never came to fruition.[35]

In 2003, O'Leary became a co-investor and director in Storage Now, a developer of climate-controlled storage facilities, putting $500,000 capital for 13% equity in the business. O'Leary learned about this opportunity through Toronto entrepreneur Reza Satchu. Through a series of real estate development and storage projects and acquisitions, Storage Now became Canada’s third-largest owner/operator of storage services, with facilities in 11 cities serving such companies as Merck and Pfizer when it was acquired by the In Storage REIT in March 2007 for $110 million.[32] As a result of that acquisition, O'Leary's sale of his shares brought him over $4.5 million from his initial $500,000 investment.[36]

In March 2007, O'Leary joined the advisory board of Genstar Capital, a private equity firm that focuses on investments in selected segments of life science and 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. O’Leary also serves on the executive board of the Richard Ivey School of Business at The University of Western Ontario. He is a former co-host of SqueezePlay on Business News Network, Canada’s national business television specialty channel. O’Leary is currently working as the entrepreneur, investor, and co-host for the Discovery Channel’s Discovery Project Earth, a project that explores innovative ways man could reverse climate change.[37]

In January 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 also described his investment objectives for the fund with two ideas, which was yield and capital preservation. The fund's primary manager is Connor O’Brien, an ex Wall Street money manager born in Montreal who worked for Merrill Lynch and Lehman Brothers and also started a private equity investing firm in 1995.[23]

In September 2011, O'Leary released his book, Cold Hard Truth: On Business, Money & Life, wherein he shares his secrets, experiences, insights, and lessons on entrepreneurship, business, finance, money and life as well as advice for budding entrepreneurs.[38] A sequel to his first book called The Cold Hard Truth On Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them was followed up in 2012, which focused a greater emphasis toward personal financial money management techniques, common money mistakes, tricks and tips to earn more financial freedom each targeted toward a specific stage in a person's life.[39]

Business journalism[edit]

O'Leary served as foil to journalist Amanda Lang on The Lang and O'Leary Exchange on CBC News Network, and he also 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. He has also hosted his own CBC television show, Redemption Inc.

During a segment on the Occupy Wall Street protests on 6 October 2011 episode of the CBC News Network's The Lang & O'Leary Exchange, O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges for sounding "like a left-wing nutbar." Hedges stated afterwards that "it will be the last time [he appears on the show]" and compared the CBC to Fox News.[40] CBC's ombudsman found O'Leary's behaviour to be a violation of the public broadcaster's journalistic standards.[41]

In August 2013, O'Leary interviewed Rachel Parent, a 14-year-old anti-GMO foods activist. In the interview, O'Leary expressed concern that Parent had become a "shill" for environmentalists. The video received over 5 million views on YouTube.[42]

In January 2014, O'Leary remarked on his television show The Lang and O'Leary Exchange that the news that the world's richest 85 people owned as much wealth as the bottom half of the global population was "fantastic news."

O'Leary left CBC in August 2014 after five years with the Lang and O'Leary Exchange;[46] earlier that year it had been announced that he was leaving Dragon's Den after eight seasons.[47] O'Leary joined CTV/Bell Media on 1 September 2014, with plans to appear on Canada AM, eTalk, The Marilyn Denis Show, The Social and BNN shows and provide financial commentary for the radio stations CFRA Ottawa, CJAD Montreal and CFRB Toronto.[48] On 5 May 2015, O'Leary made an appearance on Celebrity Jeopardy, and by Final Jeopardy, he had $-2‚500, but was given $1,000 so he could still compete for money for his charity, but bet all of the money and came in third place. He still revived $10,000 for his charity. O'Leary was the only celebrity that week to finish below $0 before Final Jeopardy.

Business ventures and investments[edit]

Having carved out a niche for the O'Leary brand in the software industry, O'Leary moved on to establish the O'Leary name and brand in a multitude of industries, companies and products. Following his successful business ventures in software, storage facilities, and private equity, O'Leary has established his name in a number of other industries, including O'Leary Funds (a mutual and investment fund management firm that handles over $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),[49] O'Leary Mortgages (a mortgage firm), O'Leary books, and O'Leary Fine Wines (a winemaking company).[50][51] In April 2014, O'Leary Mortgages went out of business.[52]

On July 14, 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. The investment fund has grown to nearly $900 million in assets under management and is focused on income, capital appreciation, and wealth preservation for its clients. Partnering with FTSE Russell, leaders in factor-based or smart beta investment strategies, O'Shares FTSE US Quality Dividend ETF, is designed to be a core investment holding, providing efficient access to a portfolio of large-cap and mid-cap dividend-paying issuers in the United States where it is targeted to individual and institutional investors with a series of core long-term investment holdings, designed to provide attractive performance, limited volatility and an emphasis on income generating dividends.[53]

O'Leary has also ventured into gold investing, with five percent of his financial portfolio invested in gold. However, he does not invest in gold stocks issued by gold mining companies, as the concept of cash flow is very important to him when analysing a stock.[54][55][56] O'Leary also advises diversification where no more than 20% of one's financial portfolio should be focused on one sector.[57] He keeps 50 percent of his family trusts in equities with the half in credits and bonds.[53]

Personal life[edit]

O'Leary has been married to his wife Linda since 1990.[58] She serves as the VP of Marketing for O'Leary Wines.[59] They have two children, Trevor and Savannah O'Leary.[60] O'Leary's son Trevor is a music producer and DJ.[58] His brother Shane graduated from Queen’s University with a Bachelor of Science degree in chemical engineering and like Kevin himself, went on to obtain his MBA from the University of Western Ontario. Shane is a retired career oil and gas executive and served in many prominent corporate positions such as the Chief Operating Officer of GranTierra Energy, Vice President and Brazil Business Unit Leader, Encana Corporation, as well as President, Chief Executive Officer, and Chief Operating Officer of First Calgary Petroleums. Shane is currently a Director of Kevin's mutual fund company, O'Leary Funds Management LP.[61][62]

O’Leary currently serves on the Dean's advisory board of the Ivey Business School at The University of Western Ontario and is also the chair of the investment committee of Boston's 107-year old Hamilton Trust.[19]

He currently has a cottage on Lake Joseph in Muskoka, Ontario, Canada where he visits during summer weekends with his family. He owns additional homes in Boston, Toronto, and Geneva.[63][64][65] His personal interests beyond his career include cooking, winemaking, playing guitar, squash, visual art, music and photography. He is an avid guitar player, remains a fan of Les Paul guitars, and personally owns a large collection, including a signed one by Les Paul. He also has a rare pen collection, a collection of 129,000 songs both digitally and from vinyl, as well as a cellar of wine from Burgundy and Bordeaux.[66]

Having a lifelong interest in photography, O'Leary is also a part-time photographer. He cites his successful career for giving him "ample time and resources" to further explore his "real passion" for photography.[67] He holds a large collection of vintage cameras, in which one of his most prized ones is a Leica M3.[66] O'Leary has amassed hundreds of thousands of photographs, including over 300,000 negatives throughout his lifetime. He is also an investor in rare photography, calling photos an art asset class that has appreciated for more than 20 years. His photography portfolio, heavily skewed toward Canadian photographers, features works by Edward Burtynsky, Barbara Cole, Joshua Jensen-Nagle and Astrid Kirchherr.[8] He held his first photo exhibition in October 2013, "Kevin O’Leary: 40 Years of Photography" at First Canadian Place in Toronto. Shooting locations for these photos included Ukraine, South Africa, Puerto Rico, and Hawaii. The exhibit generated over $97,000.[14] O’Leary also announced that the proceeds generated from the exhibit went toward his Future Dragon Fund Contest, a contest targeted towards ambitious teenage entrepreneurs in their junior and senior years.[14][68][69]



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External links[edit]