When most people think of Kevin O’Leary, they probably picture him sitting behind a desk on the hit show “Shark Tank” with a stack of cash in front of him. While O’Leary has certainly gained fame from his role as a “shark” on the popular reality show, his success as an entrepreneur started long before that. O’Leary began his career by founding SoftKey Software Products, a company that produced educational and reference software, in his basement in the late 1980s. Through strategic acquisitions and smart business decisions, O’Leary grew SoftKey into a multi-billion dollar company, eventually selling it to Mattel for $3.7 billion in 1999.

After his big payday, O’Leary continued to be involved in the world of business, becoming an early investor in the internet startup company, The Learning Company. He also ventured into the world of wine and spirits, creating the company O’Leary Fine Wines and later acquiring the Canadian franchise of Wine Rack stores. However, it wasn’t until O’Leary joined the cast of “Shark Tank” in 2009 that he truly became a household name and a symbol of entrepreneurial success. With his sharp wit and no-nonsense attitude, O’Leary quickly became a fan favorite on the show, investing in