Kevin O'Leary began his entrepreneurial journey by launching SoftKey Software Products from his basement. He expanded the company through a series of acquisitions from 1995 to 1999, buying out competitors such as Mindscape, Broderbund, and The Learning Company. In 1999, he sold SoftKey Software Products to the Mattel Toy Company for $4.2 billion, marking one of the largest deals in the consumer software industry.