From there, he joined Genstar Capital and created O’Leary Funds. When he left, he invested $500,000 of his payout in StorageNow Holdings, which he later sold for over $4.5 million. The company was buried in over $1 billion of accumulated debt by the time Mattel took over. Although he sold TLC to Mattel for $4.2 billion, he only reportedly netted about $11.2 million from the deal. This is because he’s an investing wizard who made money from a variety of sources. O’Leary’s fortune isn’t as easy to pin down as it is for many other notable wealthy people. Of course, both men profited through billion-dollar exits from what turned out to be failed tech companies during the height of the dotcom bubble. This would be considered the biggest business blunder from the Shark Tank cast if not for Yahoo!’s disastrous $5.7 billion acquisition of Mark Cuban’s. This acquisition lost Mattel $3 billion in shareholder value within a single day, prompting a class-action lawsuit that was settled for $122 million in 2003. TLC also spent $416 million on rival Broderbund before being acquired itself by Mattel for $4.2 billion in 1999. The company filled retail shelves with mostly shareware compilations but made enough money to acquire The Learning Company for $606 million in 1995 and took its name. His first notable job was as the assistant brand manager for Nabisco’s cat food brand in Toronto.Īfter a short stint as a television producer, he started Softkey. He originally wanted to be a photographer but followed his parents’ lead to become a businessmen and investor. O’Leary was born and raised in Canada, and his father died when he was only 7 years old.
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