Kevin O’Leary became a millionaire from a $4.2 billion deal—but said it was ‘very anticlimactic’

Although Kevin O’Leary became a millionaire more than 25 years ago after selling his software company Softkey Products to Mattel for $4.2 billion in 1999, he said he still remembers the exact moment he made it big. “I get asked all the time, do you remember the moment that you became a millionaire? I do,” the Shark Tank star known as Mr. Wonderful said in a video posted to his LinkedIn in July. “But have to admit, it was very anticlimatic.” How Kevin O’Leary built his fortune O’Leary founded Softkey in 1986, and throughout the 1990s his company acquired its biggest competitors like Compton’s New Media, the Learning Co., and Minnesota Educational Computer Co. as well as Creative Wonders, Mindscape, and Broderbund.  This helped Softkey to become the world’s leader in educational, reference, and home productivity software and the second-largest consumer software company in the world at the time with more than $800 million in annual sales, 2,000 employees, and subsidiaries in 15 countries. While O’Leary’s accomplishment in selling Softkey to Mattel and becoming a millionaire may seem like a major deal, he said it didn’t feel that way.  “Boom, you wake up one day and you say, ‘Wow, this
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