Mark Cuban set a goal to become wealthy and retire by the age of 35 when he was in his 20s. He was successful in the first part: At the age of 32, Cuban sold MicroSolutions, a company that provided computer consulting services, for $6 million. But the 64-year-old is still employed today.
In a recent episode of the “Re: Thinking” podcast, Adam Grant, a psychologist at Wharton, and Cuban discussed the reasons why they continue to invest, found new businesses, and manage the Dallas Mavericks of the NBA.
“I’m not retired because I’m too competitive,” Cuban said. Cuban said his competitiveness had evolved over the years: When he was 25, his goal was to “get rich” as quickly as possible. “That drove the decisions I made,” he added.
But selling MicroSolutions caused his mindset to shift, he said. As his career gained traction, he felt his increasing influence in the business world was like a game he could continue to win. “Every entrepreneur [in] the back of their mind says, ‘I want to be that entrepreneur that disrupts an industry and changes it,’” Cuban explained. “What’s better than that?”
Plus, the more competitive you are, the more likely you find retirement dull. Retirees of any age often engage deeply in their hobbies or find volunteer opportunities to pass the time.
Kevin O’Leary, Cuban’s co-star on ABC’s “Shark Tank,” has spoken about a similar dynamic. In 1999, O’Leary and his co-founders sold Softkey Software Products — later called The Learning Company — to the Mattel Toy Company for $4.2 billion. O’Leary promptly retired at age 36 and ultimately regretted it.
“I achieved great liquidity, and I thought to myself, ‘Hey, I’m 36, I can retire now,’” O’Leary told CNBC Make It in 2019. “I retired for three years. I was bored out of my mind.” O’Leary came out of retirement for the same reason Cuban won’t quit: Working provides him with challenge and a sense of identity, he said.
“Working is not just about money,” O’Leary, 68, said. “Work defines who you are. It provides a place where you’re socializing with people; it gives you interaction with people all day long in an interesting way. It even helps you live longer and is very good for brain health.”
A 2014 National Bureau of Economic Research study indicated that continuing to work after the age of 60 can keep one mentally sharp and socially active. Cuban doesn’t appear to be contemplating a full-scale retirement anytime soon: Earlier this year, he introduced Cost Plus Medicines, an online pharmacy that aims to reduce the cost of prescription medications.
He still has a significant role with the Mavericks and continues to appear on “Shark Tank,” though he has made hints that he might leave the TV programme in the coming years.
The choice to launch Cost Plus Drugs demonstrates how much Cuban’s perspective has evolved since he was 25 years old; he told Grant that he is now attempting to maximise the social impact that a financially viable business can have rather than pursuing the business idea that could make him the most money.
If I do this again when I’m 25 years old, I’m probably asking, “Alright, what can I do to get acquired?” Castro said. Yet, my next dollar’s marginal worth is now [minimum]. My life won’t be significantly changed by it. So, I make decisions in a totally different way.