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O'Leary has a holding business, called "Something Wonderful", for handling his Dragons' Den as well as Shark Tank investments. In 2008, interactive trading.com O'Leary co-founded O'Leary Funds Inc., a shared fund business concentrated on international yield investing. He is the firm's chairman and also lead financier, while his sibling Shane O'Leary offers as the supervisor.

O'Leary co-founded SoftKey Software Products, an innovation firm that sold software application tailored towards family members education and learning and also amusement. SoftKey later on altered its name to The Learning Company and was gotten by The Mattel Toy Company in 1999, with the sale making O'Leary a multimillionaire. O'Leary was quickly terminated by Mattel after the procurement resulted in substantial losses as well as numerous shareholder suits.


O'Leary credit ratings his later success at The Learning Company to the abilities he created in marketing throughout his days at Nabisco. O'Leary was birthed in Montreal, Quebec, Canada, the child of Georgette (née Bukalam), a small-business owner as well as financier, as well as Terry O'Leary, a sales person. O'Leary blamed the innovation meltdown and a culture clash of monitoring of the 2 companies for the failing of the acquisition.