kevin o'leary shark tank

Kevin O’Leary, AKA Mr. Wonderful, is well known for his audacious role on “Shark Tank” however his history within the business sector has earned him the right to have such a brazen voice in the show. Let’s take a closer look at the man behind the legend and how he came to be the success he is today.

Kevin O’Leary was born in Montreal, Quebec Canada. Learning much from his mother, Kevin began investing his money in high school and took an active interest in how to manage funds properly. His mother taught him to only spend the dividends of his investment and never the principal. That was a lesson that stuck with him for the rest of his life.

O’Leary’s life was forever changed by his very first job at an Ice Cream Parlor when his boss demanded that he scrape gum off the floor. His response was simply, “No” and so he was fired. He vowed then and there to be self-employed for the rest of his life. That moment moved him to attend university despite wanting to be a photographer, and he eventually went on to earn an MBA in entrepreneurship from the Ivey Business School at The University of Western Ontario.

During his time at University, O’Leary took a summer placement job with Nabisco in downtown Toronto. He worked with the company as an assistant brand manager, marketing their cat food after his internship, and was in charge of increasing the brand’s market share.

After his time with Nabisco, he went on to work as a television producer. Shortly thereafter, he founded Special Event Television (SET) and enjoyed moderate success with this venture. One of his partners later bought out his stake in the company for $25,000.

Next up O’Leary decided to launch another successful venture, Softkey, a repackager of high-end business software for the consumer market. He secured an investor for $250,000, who later backed out before signing paperwork, and he was ultimately left to find funding elsewhere. Taking the $25,000 he had earned from his sale of SET, O’Leary was able to secure an additional $10,000 from his mother. To get distribution for the software, O’Leary approached printer manufacturers pitching a bundle with their software. It worked. By 1994, Softkey was a billion-dollar consolidator in the educational software market, and acquired more than 60 rival companies. Softkey had wiped out the competition thanks to O’Leary’s often unpleasant and fanatical approach to business. Two years later in 1996 Softkey acquired The Learning Company (TLC) for $606 million and took its name. The company was eventually sold by O’Leary for a whopping $4.2 billion to Mattel in 1999. In 2008 he co-founded O’Leary Funds Inc. (a mutual and investment fund management firm that handles over $1.5 billion) with his brother and company director Shane O’Leary. He has built companies bearing his name in a number of other industries including O’Leary Ventures, O’Leary Mortgages,  O’Leary books, and O’Leary Fine Wines.

O’Leary has also dabbled in writing and journalism, and released his first book in 2011 entitled, Cold Hard Truth: On Business, Money & Life. He followed up that book with The Cold Hard Truth On Men, Women and Money: 50 Common Money Mistakes and How To Avoid Them.

O’Leary has appeared on numerous television shows both on and off camera. His resume includes SqueezePlay on the Business News Network, Discovery Project Earth, Dragon’s Den, and of course Shark Tank.

Tenacious, determined, and highly skilled in business, O’Leary will undoubtedly go down as one of the savviest business entrepreneurs of the 21st century.

Kevin shares lessons on life and business in his books, Cold Hard Truth On Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, Cold Hard Truth: On Business, Money & Life, and Cold Hard Truth on Family, Kids and Money.