Mark Cuban has described the moment he became a millionaire as the day he stopped wearing a watch, saying he wanted control over his own time rather than living according to someone else’s schedule.
Cuban recalled selling software company MicroSolutions in 1990 for $6 million, from which he made about $2 million. “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,’” he said.
Speaking on The Diary of a CEO podcast with Steven Bartlett, Cuban said becoming wealthy was not his main ambition. “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.”
His parents, he added, had not enjoyed the same freedom. “They always were obligated to somebody else. They had to show up at work,” Cuban said.
The 68-year-old billionaire has since relaxed his rule and now wears an Apple Watch to track data. But he said the principle still influenced his approach to clothing and business.
“Why I won’t wear a tie? Swag isn’t how you dress,” Cuban said. “Swag is being able to tell somebody else how they dress.”
The former majority owner of the NBA’s Dallas Mavericks also said he favoured email over telephone calls because it gave him more time to prepare a considered response. In a 2016 question-and-answer session, he described avoiding meetings and calls unless someone was handing him a cheque as his best life hack, saying it saved him hours each day.
How Mark Cuban built his financial independence
Cuban’s desire to prove himself began during a working-class upbringing outside Pittsburgh. He described himself at school as the “fat kid” who would do almost anything to attract attention, including wearing a T-shirt with profanity and stapling a ripped pair of jeans back together.
He said feelings of insecurity drove him to “prove people wrong”. Indiana University offered what he saw as a fresh start, and he covered the cost of his junior year by running a chain letter from his dormitory.
After graduating, Cuban moved to Dallas and worked in software sales before being dismissed by his employer. He then founded MicroSolutions, which he later sold.
Rather than reinvesting the proceeds, Cuban said he used the money to buy a lifetime pass on American Airlines. He described his aim at the time as wanting to “get as f-cked up as possible with as many people as possible in as many countries as possible, and just enjoy.”
His wealth grew substantially after he founded Broadcast.com and sold it to Yahoo in 1999 for $5.7 billion in stock. The deal took Cuban’s net worth above $1 billion and, he said, allowed him to stop worrying about what would come next.
“Because it meant instead of hustling and worrying about what came next, I got to do whatever the f-ck I wanted to do, and that was the beauty of the whole thing,” he said.
Cuban bought the Dallas Mavericks for $285 million in 2000, later selling his majority stake in late 2023 in a deal valued at $3.5 billion. He is now focused on Mark Cuban Cost Plus Drugs, a business launched in 2022 that sells generic and selected branded prescriptions directly to consumers and healthcare providers.
Despite his fortune, Cuban said money could not fundamentally change a person’s character. “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: “I like being rich a whole lot more than I like being broke.”
