David Awoyode
“Shark Tank” star and investor Kevin O’Leary has no plans to ever step away from the spotlight or business. Speaking to Business Insider in a wide-ranging interview, the 71-year-old quipped, “I’m never going to retire — because I’m a vampire,” leaning into his reputation as a ruthless capitalist.
Staying Sharp Through Work and Challenge
O’Leary, who co-founded SoftKey in the 1980s and later sold it to Mattel for $4.2 billion, says working past 60 keeps the mind active. He believes that stepping outside one’s comfort zone and taking on challenges that create “a little stress” are essential for staying physically and mentally healthy.
He admitted he thrives on competition:
“I just love it when people say I can’t do something. It motivates me to go and prove them wrong.”
From Boardroom to Big Screen
O’Leary’s latest venture isn’t a startup or investment — it’s Hollywood. He’s set to appear alongside Timothée Chalamet in “Marty Supreme,” directed by Uncut Gems filmmaker Josh Safdie.
Initially hesitant due to his lack of acting experience, O’Leary says producers reassured him:
“We don’t care. We’re not asking you to act — we just want that guy from ‘Shark Tank.’”
The role landed him fourth billing in the trailer, right behind Chalamet, Gwyneth Paltrow, and Odessa A’zion.
Lifestyle Rules for Longevity
O’Leary is passionate about health and longevity — he avoids smoking and drugs, exercises daily, and watches his diet. His one “sin,” he says, is drinking wine too close to bedtime, which sometimes disrupts his sleep.
Rolling With Life’s Ups and Downs
The investor likens life to constant “volatility.” Recently, he received two calls within minutes — one about a lawsuit against a company he invested in, the other about a separate investment going public, netting him 43 times his money.
“One moment there’s despair, the next there’s euphoria. You’ve got to roll with it,” he said.
Charles Esther