Early life and education

O'Leary was born in Montreal, Quebec, the son of Georgette (Bookalam), a seamstress turned small businesswoman and investor, and Terry O'Leary, a salesman. His father was Irish, and his mother was born in Canada, to Lebanese parents, Akaber and Joseph Bookalam. O'Leary's maternal grandfather, whose name was the Anglicized version of the name Yusef Bukalam or Abukalam, meaning in Arabic the father (abu) of the speech (kalam), was a businessman who immigrated to Canada in 1904 from a small village in Lebanon at the age of 16. Bookalam was employed at the general store of an uncle in Cobalt, Ontario and then worked as a roving salesman. He later married O'Leary's maternal grandmother, who was from the same village as Joseph, and had four children. Bookalam moved to Montreal and established Kiddie Togs, a clothing store that made children's clothing.

After Bookalam's death, O'Leary's mother ran the business, working as the store's seamstress. O'Leary's parents divorced when he was a child and his father died shortly thereafter. His mother later married an economist who worked with the UN's International Labour Organization. Due to his stepfather's international assignments, O'Leary lived in many places, moving frequently. He spent time in Cambodia, Tunisia, and Cyprus, where he learned about world cultures. O'Leary attended Montreal schools Stanstead College and St. George's School.

O'Leary developed an interest in business and investing at a young age and credits his mother, Georgette, with sparking his interest in and passing on her talent in business. Despite being a seamstress, Georgette was a skilled investor, investing a third of her weekly paycheque in 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 his mother's skill as executor of her estate after she died. As a boy, O'Leary recalls his mother telling him, "never spend the principal only the dividends." Many of his investment lessons came from his mother. 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.

At Nepean High School in Ottawa, O'Leary was a member of the photo club and bought himself a Soviet Zenit camera and began to develop his own photos. He also worked odd jobs after school to supplement his income, one of which involved washing trucks and working at an ice cream shop. 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. After graduating, he studied for two years at the Royal Military College Saint-Jean.

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 stable career path; only a small percentage of photographers achieve fame and fortune, or even have a stable income. Taking a reality check and refocusing his career options, he was unwilling to take the risk of a second job to support his dreams. O'Leary then put his artistic aspirations on hold to attend university at the insistence of his father, where he continued to develop an interest in business and investing. He attended the University of Waterloo, where he received an honours bachelor's degree in environmental studies and psychology in 1977. He also earned an MBA in entrepreneurship from the Ivey Business School at The University of Western Ontario in 1980. While working towards his MBA at the University of Western Ontario, O'Leary proposed to his professors that he produce a documentary for his 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 as giving him the necessary skills for one of his first business ventures, Special Event Television.

Business career

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 for their cat food, after earning the position from his summer internship. His main task was to increase market share for Nabisco's biggest 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. His ownership was later bought out for $25,000 by one of his partners.

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, and 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. Because of this, he learned the critical lesson of always having more than one source of financing available when starting a new business. He used the proceeds 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. 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.

Upon witnessing the potential fortunes that were to be made in the emerging software and personal computer industries of 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. 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 games packaged in "jewel-case" CD-ROMs. Due to this success, O'Leary abandoned his initial distribution strategy and turned to something more cost-effective; 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 still prospered 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 over the company's control of their market share. Reading through daily market share data, O'Leary would often become insensitive towards his partners if the company even slipped a single point in one category. O'Leary's brutally blunt and demanding demeanor, and fierce drive resulted in Softkey wiping out competitors via acquisitions and scrapping products in these companies' 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, moved its headquarters to Boston, and changed its name to The Learning Company.

TLC grossed more than USD$800 million in 1998 alone, despite recording a loss USD$105 million and losses over the previous two years. 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. Mattel needed to leverage The Learning Company's interactive software to take Barbie, Hot Wheels and its iconic brands into the interactive world and develop new revenue streams for the company. O'Leary later sold the company in 1999, for USD$4.2 billion to Mattel. 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. Though O'Leary had signed a contract to stay with Mattel for three years, six months after the deal closed O'Leary was fired. Following the acquisition, Mattel experienced a USD$105 million loss where management had projected a US$50-million profit. This caused Mattel's stock to crash, wiping out USD$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 its acquisition. The lawsuit alleged TLC used accounting tricks to hide losses and inflate quarterly revenues. O'Leary and his defendants disputed all of the charges, and none of the allegations were proven in court. Mattel paid $122 million to settle in 2003. O'Leary primarily blamed the financial meltdown on the culture clash between the two companies.

After moving on from the legal issues associated with the sale of The Learning Company, some of O'Leary's first business ventures lead to financial misfortune. Along with backers from Citigroup, O'Leary unsuccessfully attempted to purchase the video game company Atari. At the same time, O'Leary made plans to start a video-gaming television channel which 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. They produced facilities for many technology and pharmaceutical companies, such as Merck & Co., Inc., Pfizer Inc., and Johnson & Johnson. O'Leary learned of the opportunity through Toronto entrepreneur Reza Satchu, and invested $500,000 for a 13% equity in the business. Through a series of real estate development, storage projects, and acquisitions, Storage Now became the third-largest owner and operator of storage services in Canada, with facilities in 11 cities. They were acquired by In Storage REIT in March 2007 for $110 million. O'Leary sold his shares, originally bought for $500,000, for over $4.5 million.

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 from 2011 to $1.2-billion in 2012. The fund's primary manager is Connor O'Brien, an ex-Wall Street money manager born in Montreal. He worked for Merrill Lynch, Lehman Brothers, and also started a private equity investing firm in 1995. The two met and saw a lot in potential and commonality in terms of investment style and interest and entrepreneurial drive. O'Brien also chose to work with O'Leary as hewas known for being calm and practical and making good business decisions efficiently. With regards to TSX stocks, O'Leary usually focuses on companies that have nothing associated with oil and gas and companies that sell more than 50 percent of their goods 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. 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.

Writing career

In September 2011, O'Leary released his first book, Cold Hard Truth: On Business, Money & Life. He shares his secrets, experiences, insights, and lessons on entrepreneurship, business, finance, money and life, as well as advice for budding entrepreneurs. A sequel, called The Cold Hard Truth On Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, came out 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, where he delves into subjects relating to important life choices: education, careers, marriage, and family. O'Leary also focuses on the obstacles of raising a family while working diligently to provide financial security for them. He goes through the stages of a person's life and 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, and managing debt and credit. Throughout his books, O'Leary has often cites the freedom that money brings, stemming from a lesson he learned from his mother Georgette. Her family immigrated to Canada, from Lebanon, with no money and later built up a successful clothing business in Montreal.

Entertainment media

O'Leary is a former co-host of SqueezePlay on Business News Network, 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. Despite this, O'Leary has expressed scepticism about the scientific consensus on climate change, saying that he doesn't "buy" that sea levels are already rising and some weather-related events emerging, and 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 developed the sarcastic 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., a competition in which he aims to help ex-prison convicts with starting and developing their own businesses.

During a segment on the Occupy Wall Street protests on the 6 October 2011 episode of 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 " 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 the CBC, having left Dragon's Den following season 8, 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 re-join BNN, serve as a contributor for CTV programs, and as a financial commentator for Bell Media news radio stations.

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.

On 13 September 2015, O'Leary appeared as a celebrity judge in the 95th Miss America pageant.

Business ventures and investments

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), 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. 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. On October 15, 2015, O'Leary Funds was sold to Canoe Financial, a private investment management company owned by Canadian businessman W. Brett Wilson, who once sat alongside as a fellow investor with O'Leary on CBC’s Dragons’ Den.

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. O'Leary also advises diversification in multiple industry sectors where no more than 20% of one's financial portfolio should be focused on one sector. Cash flow is on main objectives O'Leary looks to achieve when analysing any investment and has a strong preference for stocks that pay dividends because he receives monthly checks. He prioritizes reliable income-producing investments that pay regular dividends, interest or distributions as consistent cash flowing in is less of a financial worry regardless of daily stock price fluctuations and macroeconomic vagaries. 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".

Political ambitions

In January 2016, O'Leary expressed interest in running for the leadership 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 attempted to stir political controversy by offering to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley. O'Leary, along with four other prospective leadership candidates, spoke at a conference for federal Conservatives in late February of 2016 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 as well as a major 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.

Personal life

O'Leary has been married to his wife Linda since 1990. She serves as the VP of Marketing for O'Leary Wines. They have two children, Trevor and Savannah O'Leary. O'Leary's son Trevor is a music producer and DJ. 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.

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.

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. 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.

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.

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. He holds a large collection of vintage cameras, in which one of his most prized is a Leica M3. 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. 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. 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.

Bibliography

• Cold Hard Truth: On Business, Money & Life. Doubleday Canada. 2011. ISBN 978-0385671743
• Cold Hard Truth on Men, Women & Money. Doubleday Canada. 2012. ISBN 978-0-385-67850-6
• Cold Hard Truth on Family, Kids and Money. Doubleday Canada. 2013. ISBN 978-0385682404

[ Source: Wikipedia ]