2. Income & Salary
O’Leary’s first professional venture was Special Event Television, a small production company that made commercials for local hockey teams to show between periods. He eventually sold his interest in the company for $25,000 to the remaining partners. His next business started with a $10,000 loan from his mother and became a massive success. O’Leary and two partners built an educational software company that eventually became known as The Learning Company. Mattel, Inc. acquired The Learning Company in 1999 for $3.8 billion. In 2003, O’Leary invested in Storage Now, which has become Canada’s third-largest climate-controlled storage facility company.