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The Reason Why Kevin O’Leary is Also Mr. Wonderful in Real Life




Kevin O’Leary’s diverse heritage, his father is of Lebanese descent and his mother is of Irish descent, gave him an aggressive but positive approach that made him become a successful entrepreneur. Let us give a closer look into the life of Mr. Wonderful, Kevin O’Leary.

Who Is Kevin O’leary

Terence Thomas Kevin O’Leary or more popularly known as Kevin O’Leary is a Canadian businessman, author, and TV personality. He is one of the co-founders of the software company “SoftKey”. He was born on July 9, 1954, in Montreal, Quebec, Canada. His parents, Georgette and Terry O’Leary were small-time business owners and investors. They divorced when Kevin was just a child because of his father’s alcoholism, shortly after the divorce, his father died which made his mother taking over the family business. His mother later married an economist, George Kanawaty, who worked with the UN’s International Labour Organization. His stepfather’s international assignments caused the family to move frequently, and Kevin lived in many places while growing up, including Cambodia, Ethiopia, Tunisia, and Cyprus. Kevin attended Stanstead College and St. George’s School, both in Quebec. Initially, he aspired to be a photographer but due to the advice of his step-father, he pursued his interest in business and investment. He received his bachelor’s of Environmental Studies and Psychology from the University of Waterloo and his MBA in Entrepreneurship from the University of Western Ontario in 1980.

O’leary’s Business Career

While pursuing his MBA, he started his career with an internship at a company named “Nabisco” in Toronto. Later, he was promoted to the position of assistant brand manager for the company’s cat-food brand. Kevin later said that a lot of his learnings had come from “Nabisco” and it had enabled him to make some successful decisions when he started his own company. After leaving Nabisco, he began a brief career as a television producer. With two of his former MBA classmates, Scott Mackenzie, and Dave Toms, Kevin co-founded the Special Event Television (SET). SET was an independent television production company that produced original sports programmings 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. 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.

After selling his share of SET, O’Leary started Softkey in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock. The company was a publisher and distributor of CD-ROM-based personal computer software for Windows and Macintosh computers. It was the first Canadian company that applied the model of consumer goods to the computer software industry. 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 emerged as competition to ‘SoftKey’ were eventually acquired by the company. In 1995, ‘SoftKey’ made a major announcement about acquiring ‘The Learning Company’ for a humongous amount of $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 recent history.

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.

O’leary’s Tv and Political Career

In 2006, Kevin appeared as one of the five venture capitalists on the then-new show Dragons’ Den on CBC. On the show, O’Leary developed a persona as a blunt, abrasive investor, who at one point told a contestant who started crying, “Money doesn’t care. Your tears don’t add any value.” This television persona was encouraged by executive producer Stuart Coxe, who during the first two seasons occasionally asked O’Leary to be “more evil”. Dragons’ Den became one of the most-watched shows in CBC history, with around two million viewers per episode. In 2009, Kevin appeared as one of the judges in the American installment of the show ‘Dragons’ Den,’ titled ‘Shark Tank.’ Kevin left the show in 2014.

Kevin’s appearances on Dragons’ Den and Shark Tank popularized the nickname “Mr. Wonderful” for him; he has said that he is often referred to by that name in public. He said that the nickname serves both as a tongue-in-cheek reference to his reputation for being mean, as well as a reflection of his view that his blunt assessments are helpful to misguided entrepreneurs.

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 a lack of support from Quebec.

Top 3 Tips for Entrepreneurs From Kevin O’leary

“What are the most important qualities that make a successful entrepreneur? The ability to communicate. The ability to express your idea with certainty. That’s how you become a leader even if you are unsure, your ability to explain your vision and your direction is the attribute you need the most. … Articulate your idea in 90 seconds or less.”

“I actually think being an entrepreneur is a state of mind. If you’re going to be an entrepreneur, my thesis is that you have to sacrifice everything for some period in your life to be successful. You have to be myopic and completely focused and unbalanced in every way. Once you’ve achieved success, you’re free to do whatever you like.”

“My partners… taught me that in order to create wealth, I needed to pair up with people whose strengths compensated for my weaknesses.”

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