Childhood & Early Life
Kevin O’Leary was born Terence Thomas Kevin O’Leary, in Montreal, Quebec, Canada, on July 9, 1954, to Terry and Georgette O’Leary. His mother, Georgette, was a small-time business owner and investor. His father, Terry, was a salesman. His father was Irish, and Kevin holds Irish citizenship since birth. He grew up with his brother, Shane.
Life was not too easy for Kevin while growing up. His father was faced with lack of finances at work and had turned into an alcoholic over time. This led to his parents’ bitter divorce. His father passed away soon after, and following that, his mother ran the family business herself.
His mother later married an economist named George Kanawaty, who worked with the ‘United Nations’ agency ‘International Labour Organization’ (ILO). Due to his stepfather’s job that had him constantly moving from one place to another, Kevin also moved with the family. He spent a great chunk of his childhood in Tunisia, Cambodia, and Cyprus.
His mother had a major role in Kevin’s interest in business. He had started working in his teenage years. One of his first jobs was at an ice-cream parlor.
After graduating high school from ‘St. George’s School’ in Quebec, Kevin attended ‘Stanstead College’ for his bachelor’s degree. He later attended the ‘University of Waterloo’ and graduated in environmental studies and psychology. Although he initially wanted to become a photographer, his mother’s influence made him decide to pursue business.
He attended the ‘Ivey Business School’ of the ‘University of Western Ontario’ and graduated with an MBA degree in 1980. His mother passed away while he was in college. Only after he was presented with her will did he come to know about his mother’s fine investment skills. He studied the techniques his mother had used and planned his future based on that knowledge.
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While pursuing MBA, he started his career with an internship at a company named ‘Nabisco’ in Toronto. Later, he was promoted to the position of the assistant brand manager for the company’s cat-food brand. Kevin later said that a lot of his learning had come from ‘Nabisco’ and had enabled him to make some successful decisions when he started his own company.
Following his MBA, Kevin started looking for a job. Kevin started a brief career as a TV producer, along with two of his MBA classmates, Dave Toms and Scott Mackenzie. Sometime later, the three of them founded their sports broadcasting company, ‘Special Event Television’ (SET).
The company worked independently and broadcast some crucial sporting events such as ‘The Original Six’ and the ‘Hockey Legends.’ The company also produced low-budget TV shows, soccer documentaries, and other sports documentaries. However, Kevin had bigger aspirations. He sold his share in the company to one of his partners and started working independently on starting his own company.
It was the mid-1980s and computers had just started becoming popular. Kevin seized the opportunity and laid the foundation of his own software product company, ‘SoftKey,’ in 1986. He founded the company along with John Freeman and Gary Babcock. It was the first Canadian company that applied the model of consumer goods to the computer software industry.
As computers became cheaper in the coming years, more and more families bought them, thereby increasing the demand for software. ‘SoftKey’ manufactured and sold educational and entertainment software. By the late 1980s, the company became huge.
Several more companies started following the same business model, but all the competition was destroyed by the tactical business mind that Kevin possessed. The companies that gave strong competition to ‘SoftKey’ were eventually acquired by the company. By the early 1990s, ‘SoftKey’ had acquired two of its biggest competitors: ‘Spinnaker Software’ and ‘Wordstar.’
In 1995, ‘SoftKey’ made a major announcement about acquiring ‘The Learning Company’ for a humongous $606 million. ‘SoftKey’ was then rebranded as ‘The Learning Company.’ Its headquarters were moved to Massachusetts, US. However, the company suffered heavy losses following the acquisition.
In 1999, Kevin handed over the company to ‘Mattel,’ a toy manufacturing company. Kevin left ‘Mattel’ when it, too, started registering heavy losses. The acquisition deal, amounting to a whopping $4.2 billion, was later called one of the most disastrous business deals in the recent history.
In the mid-2000s, Kevin planned to acquire the video game creator ‘Atari,’ but the deal never materialized. Instead, he became a co-investor and an active director at ‘StorageNow Holdings’ in 2003. He had purchased the shares in about half a million dollars. He sold them for $4.5 million 4 years later.
In 2008, he laid the foundation of ‘O’Leary Funds,’ a mutual fund company. While his brother, Shane, works as the director of the company, Kevin works as its chairman and its lead investor. Kevin made a huge fortune while investing in a few other companies and funds.
In 2006, Kevin made his TV debut with the Canadian show ‘Dragons’ Den.’ The show had a one-of-its-kind concept, enabling contestants to pitch their ideas to venture capitalists. Kevin was one of the venture capitalists on the show. He exhibited a strong and blunt persona.
In 2009, Kevin appeared as one of the judges in the American instalment of the show ‘Dragons’ Den,’ titled ‘Shark Tank.’ Kevin left the show in 2014. In 2008, he appeared in ‘Discovery Channel’s program ‘Project Earth.’
His first book, ‘Cold Hard Truth: On Business, Money & Life,’ was published in 2011. He released two more books as sequels to the first book, through which he coached his readers about his way of dealing with various aspects of life, such as education, career, and business.
Kevin also tried his hand in politics when he campaigned to become the leader of the ‘Conservative Party of Canada’ in 2017. However, he withdrew from the elections, citing lack of support from Quebec.