When Mark Cuban was a young man with big dreams, he didn’t imagine yachts and luxury right away.
Instead, he had a much simpler goal: retire by 35 and live on passive income. His plan? Save aggressively and live cheaply.
“Live like a student,” Cuban said in a 2020 interview with Muck Rack CEO Greg Galant. That was his mantra in his early years.
Inspired by the book “How to Retire at 35,” Cuban envisioned saving up a few hundred thousand dollars, living off the interest, and never having to work again.
“If I could save $100,000, interest rates were a lot higher then… 10 percent interest rate, that’s $10,000 a year,” he said.
“So if I can get up to $250,000, then I’d have $25,000. Could I live off of that? Yeah, back then I thought I could.”
The Value of Time
What made Cuban so focused on gaining financial freedom early? It wasn’t laziness. It was about owning his time.
“My dad really didn’t have his own time to himself,” Cuban said.
“He was always at the beck and call of somebody else. He would always instill in me, the most valuable asset you can ever possibly have is time.”
Once Cuban sold his first company, MicroSolutions, he symbolically ditched his watch.
“The day I sold MicroSolutions, I took off my watch and said I’d never wear a watch again,” he said.
“Because that signified I have to be somewhere and pay attention to time that other people set for me.”
O’Leary’s Take on Early Retirement
That same desire for time freedom was what drove another investor, Kevin O’Leary, to retire in his mid-30s after selling his company, Softkey for $4.2 billion. But his experience turned out quite different.
“I went to every beach on Earth,” O’Leary said. After three years, he admitted, “It was really boring.”
O’Leary realized that work gave him purpose, social engagement and mental sharpness. He eventually returned to the business world, but this time as an investor.
“This whole idea of Financial Independence, Retire Early doesn’t work,” O’Leary said.
“People think, ‘I’m going to retire early and life will be perfect,’ but they’re wrong.”
Freedom Over Fortune
Cuban never fully stepped away from work either. He just wanted the freedom to choose what he worked on and when.
“I just want to be able to do whatever I want, whenever I want, however I wanted to do it,” Cuban said. “And I got really good at it.”
So, while Cuban and O’Leary took different paths, both agree on one thing: freedom matters more than the money itself.
And for Cuban, that freedom started with living like a broke college kid and saving like it was a full-time job.
But he also shows that early retirement doesn’t mean doing nothing, it means buying back your time.
Whether you choose to keep building businesses, explore the world, or invest in others, the point is having the choice.
As Cuban and O’Leary both found, it’s not just about retiring, it’s about staying challenged, curious, and in control of your time.
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