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.
O’Leary founded Softkey in 1986, and throughout the 90s 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.
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 is interesting, but it doesn’t change anything,’” O’Leary said in the LinkedIn video. “That’s the crazy thing. And every millionaire [or] billionaire I talk to says, ‘yeah, it’s not that big a deal.’”
But that may be O’Leary reflecting on the entirety of his career. In 2003, he became co-investor and director in Storage Now and a founding SPAC investor and director of Stream Global Services in 2007.
He now holds investments in more than 30 private-venture companies, is the chairman of O’Shares ETF Investments, and automated internet-based investment advisory service company Beanstox. And, most famously, he’s been an investor on Shark Tank since the show’s premiere in 2009. O’Leary also owns several companies he founded, including O’Leary Fine Wines and O’Leary Ventures, his private venture-capital investment company.
“You work your a** off. It’s so hard. What it really takes to do is have the discipline of not buying sh*t you don’t need,” O’Leary said in the YouTube video. “To make that first mil is you’ve got to invest it. Market’s going to make you 8%. And then I thought, well my sights are on five [million]. It’s going to be impossible. It wasn’t as hard to get to five [million] as it was to one [million].”
“If you’re very passionate about what you’re doing [you’ll] wake up one morning successful,” O’Leary said in the LinkedIn video. “[The] key is the passion. It’s not the pursuit of greed or money. That doesn’t work. You’re so in love with what you’re doing in business, and you get rewarded for it, particularly if you’re solving a big problem.”
