Kevin O’Leary plans to keep working until the day he dies — and beyond.
“I’m never going to retire,” he told Business Insider in a wide-ranging interview. “That’s because I’m a vampire,” he quipped, playing up his reputation as a cold-blooded capitalist, earned from years as a “Shark Tank” investor.
O’Leary is known for cofounding SoftKey in the mid-1980s, building it into The Learning Company, then selling the educational-software business to Mattel for $4.2 billion in 1999. He’s also the founder of O’Leary Funds and O’Leary Ventures, and has invested in companies such as Basepaws on “Shark Tank.”
The 71-year-old said that working, especially past 60, keeps people’s minds sharp, and that doing things “outside of your comfort zone” that cause you some “stress” has been key to his staying healthy in body and mind as he’s aged.
The self-proclaimed “Mr. Wonderful” said he relishes competing and “being in the game.” When others predict he’ll fail at a challenge, it “just motivates me to go kick ass” in that industry, he said.
“I just love it when people say I can’t do something,” he added.
O’Leary’s latest adventure isn’t investing or starting a company: he has a major role alongside Timothée Chalamet in “Uncut Gems” director Josh Safdie’s next movie, “Marty Supreme.”
The celebrity investor told Business Insider he initially balked at the idea as he had no experience performing from a script. He recalled the producers replying, “We don’t care, we’re not asking you to act. We’re looking for a real asshole, and you’re it. We just want that guy that we know from ‘Shark Tank.'”
O’Leary said he “never looked back” and was soon on set. O’Leary’s performance is prominent in the movie’s trailer, which gives him fourth billing behind Chalamet, Gwyneth Paltrow, and Odessa A’zion.
“I think that helped me in business. I think it helped me be disciplined,” O’Leary said of the “remarkable” experience.
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Wine and worry
Asked what keeps him up at night, O’Leary replied that his “one sin” is “drinking wine too close to bedtime.”
O’Leary said he’s “really into longevity” — minding what he eats, not smoking or taking drugs, and trying to exercise daily. But he said he’s found “the older I get, the better the wine gets.”
Sleep is so vital that you “can’t let your problems keep you awake, because that’s very unhealthy,” O’Leary said.
O’Leary told Business Insider that there are always good and bad days, describing that as “volatility” in business, relationships, and life.
He said he’d recently received a “catastrophic” call from one of the entrepreneurs he had invested in, saying their company was being sued. Twenty minutes later, he learned on another call that one of his team’s investments six years ago would be going public, and he stood to make 43 times his money.
“So there’s utter despair, and a few minutes later, utter euphoria,” he said. “Sometimes the poo-poo hits the fan one hour. And then something beautiful happens the next. You’ve got to roll with it,” he added.
