Billionaire entrepreneur Mark Cuban made an unusual decision after selling his first successful business in 1990. Instead of celebrating his newfound wealth with a luxury purchase, he took off his watch and decided he would no longer wear one.
The former Shark Tank star said the decision reflected something he valued more than money, which was the freedom to manage his own time. In a recent conversation, Cuban explained why he did not want to spend his life working according to someone else's schedule.
As reported by Fortune, Cuban shared the story during an appearance on The Diary of a CEO podcast, hosted by Steven Bartlett.
“The day I sold MicroSolutions, I took off my watch and I said, ‘I’m never going to wear a watch again because that means I’m working on somebody else’s time,’” Cuban recalled.
He said becoming wealthy was not necessarily his biggest ambition. Having control over his decisions and daily life mattered more.
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{{/usCountry}}“I just thought I hated being broke,” he said. “I wanted to control my own destiny. That was a big thing, and I wanted to be able to control my own time.”
Cuban also spoke about how his parents had to work according to other people's expectations and did not enjoy the same freedom.
“They always were obligated to somebody else. They had to show up at work,” he said.
Why Mark Cuban wanted to control his own time
Cuban's approach to work reflects his preference for managing his schedule independently. He prefers emails to phone calls because they give him more time to think through his responses.
In a 2016 conversation with Thrive Global, he also described avoiding unnecessary meetings and calls as one of his biggest productivity habits. He said this helped him save several hours each day.
His rule about watches has since relaxed. Cuban now wears an Apple Watch to track data, but the thinking behind his earlier decision continues to influence his personal choices. He has also spoken about avoiding formal clothing, saying that confidence is not about what someone wears.
From selling MicroSolutions to becoming a billionaire
Cuban's journey to wealth began with MicroSolutions, the software company he founded after being fired from a job in Dallas. He sold the business in 1990 and used the money to enjoy a new level of independence rather than immediately chasing another fortune.
As Fortune reported, he bought a lifetime pass on American Airlines after the sale, allowing him to travel extensively. His next major success came with Broadcast.com, which he co-founded and later sold to Yahoo in 1999 in a stock deal valued at $5.7 billion.
The deal took his wealth past the billion-dollar mark and gave him the financial freedom to pursue interests beyond business. In 2000, he bought the NBA's Dallas Mavericks for $285 million. He later sold a majority stake in the team in a deal valued at $3.5 billion in 2023.
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Cuban is now focused on Mark Cuban Cost Plus Drugs, an online pharmacy business he launched in 2022 to make prescription medicines more affordable.
Despite his estimated $10.6 billion fortune, Cuban believes money cannot necessarily change a person's outlook on life.
“If you’re miserable when you’re poor, good chance you’re gonna be miserable when you’re rich,” he said. “Money can’t change who you are.”
He added, however, that he enjoys being wealthy much more than being broke.