“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 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, and 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.

Why the first million is the hardest

While becoming a millionaire feels like a blip on O’Leary’s radar at this point, he also said in a 2023 video on his YouTube channel that it can feel impossible to make your first million—but meeting a $5 million milestone feels much easier.

“You work your ass off. It’s so hard. What it really takes to do is have the discipline of not buying s*** 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].”

And even though O’Leary has an estimated net worth of about $400 million and pushes pitchers on Shark Tank to really know their numbers and prove their valuation, he insists it’s not about the money to him.

“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.”

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