Kevin O'Leary

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Kevin O'Leary
OLeary and Atwood.jpg
Kevin O'Leary with Margaret Atwood at the 2011 Writers' Trust of Canada Gala
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 Businessman
Television personality
Years active 1979 - present
Net worth Increase US$300 million[2][3]
Spouse(s) Linda O'Leary (since 1990)
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.

Hailed as Canada's business equivalent of Donald Trump, O'Leary is one of Canada's most prominent entrepreneurs, investors, and financial pundits.[4][5] He is the Co-founder and Chairman of O'Leary Funds and the co-founder of Softkey. He has also previously served as a business journalist on CBC's The Lang and O'Leary Exchange with Amanda Lang and hosted Redemption Inc.[6] He is mostly 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.

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.[7] He attended the University of Waterloo in Ontario, obtaining an Honours bachelor's degree and upon receiving his MBA from the University of Western Ontario, he set his sights towards carving his niche as a successful businessman.

O'Leary began his career in the early 1980s as an assistant brand manager for Nabisco Foods where he successfully 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 leading technology company that sold software geared towards family education and entertainment. SoftKey became a major force in the global educational software industry, where during the late 1980s and 1990s, it acquired many rival companies such as Compton's New Media, The Learning Company and Brøderbund. O'Leary's shrewd business acumen helped propel the company into the world leader in the development of educational, reference, and home productivity software, garnering annual sales of over $800 million, 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 multi-millionaire in the process.[8]

Early life and education[edit]

O'Leary was born in Montreal, Quebec to a Canadian father of Irish origin who worked as a salesman and a Canadian mother of Lebanese origin who was a seamstress turned small businesswoman and investor. 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.[9][10][11][12] O'Leary's maternal grandfather, Joseph Bookalam was a successful businessman who immigrated to Canada in 1904 from a small village in Lebanon at the age of 16. Bookalam had an uncle in Cobalt, Ontario 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, which provided enough startup capital for him to establish Kiddie Togs, a successful clothing store which made high end children's winter clothing.[10]

After Bookalam's untimely death, O’Leary's mother ran the business successfully for many years when working as the store's seamstress.[13] O'Leary's parents divorced when he was a child and his father died shortly thereafter. As a result of a broken marriage, he 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.[11][14][15] Due to his stepfather's international assignments, O'Leary lived in many places across the world, moving around every couple of years. He spent time in countries such as Cambodia, Tunisia, and Cyprus, where he often went out into the communities and learned about world cultures.[16] He attended Stanstead College[17] and St. George's School.[6]

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 paycheque 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.[7] 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." Many of his mother's investment lessons stem from his mother where one was to save one-third of your money, spend only the interest while protecting the principal. This lesson is what O'Leary would later employ decades later with his mutual fund management company, O’Leary Funds.[6][7][18][19]

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.[14] He also worked odd jobs after school to supplement his income, one of which involved washing trucks and working at an ice cream shop.[20] 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 and since then he has made a personal conviction to be self-employed for the rest of his life.[21] After graduating, he studied for two years at the Royal Military College Saint-Jean.[22]

After graduating from high school, O'Leary aspired to become a photographer. However, his step-father advised 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.[14] O'Leary took his fathers advice by going to university and continued to develop an interest in business and investing.[23] He attended the University of Waterloo where he received an honours bachelor's degree in environmental studies and anthropology in 1977.[24][25][26] He also earned an MBA in entrepreneurship from the Ivey Business School at The University of Western Ontario in 1980.[25][26] While working towards his MBA at the University of Western Ontario, O'Leary proposed to his professors that he produce a documentary for his MBA thesis where the subject would be to illustrate what he had learned during his two years at Ivey. In addition, O'Leary agreed to let Western use his documentary as a recruitment tool which later became a huge success, that set him apart from his classmates upon graduation. In addition, O'Leary cites the success that gave him the necessary skills needed for one of his first business ventures, Special Event Television, a television production company which he later set up with Scott Mackenzie and Dave Toms; both of whom had assisted on O'Leary’s MBA documentary.[13][27][28]

Business career[edit]

In 1979, between the first and second years of 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.[18][19][29][30] O’Leary credits his later success with The Learning Company through his well honed business skills when marketing cat food during his days at Nabisco.[31]

After leaving Nabisco, O'Leary began his brief career as a television producer before venturing into the software business. With two of his former MBA classmates Mackenzie and Dave Toms; both of whom had assisted on O'Leary’s successful 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 met limited success producing minor television shows, soccer films, sports documentaries, and short in-between-period commercials for local professional hockey games.[18][32][33][34][35] His ownership was later bought out for $25,000 by one of his partners.[6][28][36]

After selling his share of the company, O'Leary moved on to his second business venture, Softkey. A major financial backer committed $250,000 in development capital to the burgeoning company which then backed out the day before signing the documents and delivering his cheque. This predicament ultimately left O'Leary devastated and desperate for extra rounds of funding to support the fledging business and ultimately taught him the critical lesson of always having more than one source of financing available when starting a new business.[6] He later used the proceeds earned from selling his share of Special Event television and convinced his mother to lend him $10,000 in seed capital to establish SoftKey Software Products. Softkey was started in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock.[35] 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.[33] Upon witnessing the potential fortunes that were to be made in the emerging software and personal computer industries during the early 1980s, 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.[37][38] 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 1980s due to competition from other software companies, but continued to prosper throughout the 1990s under O'Leary's leadership. O'Leary was an aggressive promoter of the company's products and garnered a reputation for being fanatical about the company's control of the market share. Reading through daily market share data, O'Leary would often become insensitive towards his partners 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 scrapped products in the company's software 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.[39] In 1995, Softkey acquired The Learning Company (TLC) for $606 million, moved its headquarters to Boston, and took The Learning Company as its name.

By 1998, TLC earned more than 800 million USD in 1998 alone despite recording a loss $105 million USD and a loss over the two previous years.[9] 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.[40] Mattel needed to leverage The Learning Company's interactive software to take Barbie, Hot Wheels and its iconic brands into the interactive world to develop new revenue streams for the company.[6] O'Leary later sold the company in 1999, for 4.2 billion USD to Mattel.[35] 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.[41] 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.[9]

After moving on from the legal issues associated with the sale of The Learning Company, 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 attempted to purchase the video game company Atari, which was unsuccessful. At the same time, O'Leary made plans to start a TV video-gaming channel, which never came to fruition.[33]

In 2003, O'Leary became a co-investor and director in Storage Now, Canada's leading developer of climate controlled storage facilities for many technology and pharmaceutical companies such as Merck & Co., Inc., Pfizer Inc., and Johnson & Johnson. O'Leary invested $500,000 for 13% equity in the business.[8] 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 and operator of storage services, with facilities in 11 cities when it was acquired by the In Storage REIT in March 2007 for $110 million.[38] 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.[33]

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.[42]

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.[19] With regards to TSX stocks, O'Leary usually focuses on companies that have nothing associated with oil and gas as well as headquarters in Alberta and companies sell more than 50 percent of its good and services in the United States. When the Canadian economy fell into a technical recession during the first couple of months of 2015, O'Leary advised investors to continue to place their money into Canadian equities despite pessimism from economists.[43] 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 throughout late July 2015.[44]

On 12 August 2015, Warren Buffett acquired industrial goods and metal fabrication company Precision Castparts Corp. in a deal valued at USD$37.2billion, including the company’s debt where it marked one of Berkshire Hathaway's largest cash deals ever. In response to that deal, O'Leary responded that the deal was both expensive and potentially risky citing its 20x EBITDA operating rate as an example.[45]

Writing career[edit]

In September 2011, O'Leary released his first book, Cold Hard Truth: On Business, Money & Life, where he shares his secrets, experiences, insights, and lessons on entrepreneurship, business, finance, money and life as well as advice for budding entrepreneurs.[46] 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 financial literacy and financial education as a foundation for achieving great wealth, 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.[47] O'Leary released a followup in 2013, where he delves into subjects relating to important life choices that many people make such as education, careers, marriage, and family. O'Leary also focuses on the obstacles of providing and raising a family while working diligently to provide financial security. He goes through a walk through around every age and stages of a persons life where he offers advice related to education, career choices, dating, marriage, raising a family, and retiring. He also shares tips on instilling the value of financial literacy for every family member, saving and investing money, as well as managing debt and credit.[48] Throughout his books, O'Leary has often cited the freedom that money brings, stemming from a lesson that he learned from his mother Georgette, where her family immigrated to Canada from Lebanon with no money and later built up a successful clothing business in Montreal.[49]

Entertainment media[edit]

O'Leary is a former co-host of SqueezePlay on Business News Network, Canada’s national business television specialty channel. O’Leary also worked as a co-host for the Discovery Channel’s Discovery Project Earth, a project that explores innovative ways man could reverse climate change.[50] O'Leary has also previously 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 became well known on both shows for computing financial valuations mentally while negotiating offers with the contestants.[6] He has also produced and hosted his own reality show, Redemption Inc., a competition in which O'Leary aims to help ex-prison convicts in starting and developing their own businesses.[6]

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.[51] CBC's ombudsman found O'Leary's behaviour to be a violation of the public broadcaster's journalistic standards.[52]

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.[53]

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;[57] earlier that year it had been announced that he was leaving Dragon's Den after eight seasons.[58] 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.[59] On 5 May 2015, O'Leary made an appearance on Celebrity Jeopardy but attained $-2‚800 at the end of regular play. For Final Jeopardy, he was given $1,000 to compete for money for his charity, but lost all of this money and came in third place.[60]

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),[61] O'Leary Mortgages (a mortgage firm), O'Leary books, and O'Leary Fine Wines (a winemaking company).[62][63] In April 2014, O'Leary Mortgages went out of business.[64]

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. 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.[65]

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 gold stocks issued by gold mining companies, as the concept of cash flow is very important to him when analysing a stock.[66][67][68] O'Leary also advises diversification where no more than 20% of one's financial portfolio should be focused on one sector.[69] He keeps 50 percent of his family trusts in equities while the other half is concentrated in credits and bonds.[65]

Personal life[edit]

O'Leary has been married to his wife Linda since 1990.[70] She serves as the VP of Marketing for O'Leary Wines.[71] They have two children, Trevor and Savannah O'Leary.[72] O'Leary's son Trevor is a music producer and DJ.[70] O'Leary has one brother, Shane O'Leary. 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 has held many prominent corporate positions. He has served as the Chief Operating Officer of GranTierra Energy, Vice President and Brazil Business Unit Leader, Encana Corporation, as well as the 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.[73][74]

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.[26]

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.[27][35][75] 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.[76]

Wine has been a lifelong passion of O'Leary's. Collaborating with Vineland Estates owner Jim DeGasperis and vintners Allan and Brian Schmidt, O'Leary launched his winemaking brand with a 2010 Cabernet Merlot that won six awards, including Best Value at the 2012 InterVin International Wine Awards, one of only 10 red wines, from more than 1,000 tasted, to receive that distinction. In addition, the wine became the number-one-selling VQA red in Ontario. In addition to owning wine cellars around the world, O'Leary also trades wine futures on the international commodity markets.[49]

Having a lifelong interest in photography, O'Leary is also a part-time photographer. He cites his successful business career for giving him "ample time and resources" to further explore his "real passion" for photography.[77] He holds a large collection of vintage cameras, in which one of his most prized ones is a Leica M3.[76] 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.[14] 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.[20] 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.[20][78][79]



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