When Mark Cuban was in his 20s, his goal was to retire at age 35.
These days, the 66-year-old billionaire entrepreneur and investor says he has no imminent plans to stop working. “I’m just getting started,” Cuban tells CNBC Make It. “There’s no retirement in my book. I’ll go until I drop.”
Some of Cuban’s recent career moves have prompted speculation on the subject, from announcing his departure from ABC’s “Shark Tank” in 2025 to selling his majority stake in the NBA’s Dallas Mavericks. He’s acknowledged that he’d like to spend more time with his family, but that doesn’t mean he’s retiring, he says.
Rather, Cuban says he plans to shift the majority of his working hours toward running his direct-to-consumer online pharmacy, Cost Plus Drugs. “It’s something I’ll keep on working on for a long time,” he says.
Cuban initially invested $250,000 into Cost Plus Drugs after its founder and CEO, Alex Oshmyansky, cold-pitched him on the idea in 2018. Over the following two years, Cuban invested more and more until he eventually owned the company.
The company’s simple business model — reducing consumer costs by manufacturing drugs, or buying them wholesale, and selling them at a 15% upcharge — is profitable, but Cuban says he’s more focused on the company’s mission than maximizing the return on his investments.
“Hopefully, when it’s all said and done, they’ll say, ‘Boy, that guy f—ed up health care, so now people aren’t afraid of not being able to afford their medications,” he says. “To me, that would be the greatest accomplishment.”
Retiring, then un-retiring, in his 30s
At age 25, Cuban says he was fully committed to the FIRE ethos, which stands for “financial independence, retire early.” The idea is to embrace a frugal lifestyle and maximize your savings to retire sooner.
“My whole goal when I started [working] was to retire by the time I was 35, because the one thing you can never buy is time,” Cuban said on “Shark Tank” in 2021. He started saving and investing large portions of his paycheck after reading the 1988 book “Cashing in on the American Dream: How to Retire at 35” by Paul Terhost, he told CNN Money in 2017.
In 1990, Cuban sold his first company, a software startup called MicroSolutions, to CompuServe for $6 million. After the sale, “I literally retired,” he told Bloomberg in 2020. “I bought a lifetime pass at American Airlines, traveled the world and partied like a rock star for the next few years.”
Five years later, Cuban was back to work, taking over the audio streaming company Broadcast.com alongside his friend Todd Wagner. He’d realized he was “too competitive” to retire early, and missed the thrill of a promising investment, he told Wharton organizational psychologist Adam Grant’s “Re:Thinking” podcast in 2022.
Broadcast.com made Cuban a billionaire when Yahoo acquired it for $5.7 billion in stock in 1999. His current net worth is roughly $5.7 billion, Forbes estimates, and he’s said that his wealth enables him to prioritize his competitive spirit over money.
“Every entrepreneur [in] the back of their mind says, ‘I want to be that entrepreneur that disrupts an industry and changes it,'” Cuban told Grant. “What’s better than that?”
More Americans are working longer — including some of the rich
Cuban’s desire to work more is hardly unusual: More Americans are now working past age 75 than ever.
In 2022, 8% of people over age 75 were working in the U.S., according to the Bureau of Labor Statistics — up from 5% in 2002. By 2032, one in 10 people over age 75 will continue to work, according to a Labor Department projection.
Americans have increasingly long life spans. Some say their attitudes about retirement are changing, or their savings are insufficient. Others say they enjoy what they do, and never contemplated giving work up.
The trend extends to at least one other billionaire: The thought of working less than full-time “sounds awful,” billionaire Microsoft co-founder and philanthropist Bill Gates told Make It earlier this month.
Gates said he hopes to follow in the footsteps of his longtime friend Warren Buffett, who currently serves as chairman and CEO of Berkshire Hathaway at age 94 and reportedly has no plans to retire.
“My friend Warren Buffett still comes into the office six days a week,” said Gates, 68. “So, I hope my health allows me to be like Warren.”
Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank.”
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