His background is in software, and he got his start with SoftKey Software Products, which he started from his basement. This was in the 1990s, when the computer world was still rapidly evolving. All those growing pains led to O’Leary’s ascension to the role of president at The Learning Company.
The Learning Company was then responsible for popular educational computer games like The Oregon Trail, Reader Rabbit, and the Carmen Sandiego geography game franchise. O’Leary left the company in 2000, a year after it was sold to the toy-making tycoons at Mattel in a $3.7 billion deal.
Since then, he has put his entrepreneurial spirit to work in new business ventures. He started the mutual fund company O’Leary Funds to manage his own wealth and share his investing philosophy with others. He is also involved in Storage Now, the third largest storage services company in Canada.
He is also a member of the advisory board at Genstar Capital, and he works hard to find worthwhile investments that have a positive impact on the environment.
O’Leary is no stranger to the TV cameras, having appeared on several Canadian series, including Canada’s version of Shark Tank, which is called Dragons’ Den. In the Dragons’ Den, he is joined by fellow Shark Tank investor Robert Herjavec.
When he’s not making money or scowling for the camera, he can be found at his remote Canadian estate with his family, where he enjoys playing the guitar and learning about wine.
Kevin O’Leary on Shark Tank is a notoriously hard sell, but he has opened up his checkbook a few times for the show’s entrepreneurs. His investments have included: the Caffeindicator, a sweetener than changes colors in the presence of caffeine; Jump Forward, a social marketing tool for student athletes; and First Defense Nasal Screens.