Cuban, who tries to always keep learning something new, says he constantly pushes himself to leave his comfort zone.
"Whether I've met with Steve Bannon, done 'Dancing With The Stars,' bought the [Dallas Mavericks], whatever the case may be, I just want to try new experiences and do different things," Cuban says during an interview on "The Jamie Weinstein Show" podcast.
Cuban's in good company with the idea. It's a sentiment that Bezos echos.
"Jeff Bezos — and I follow this to a T — I was reading, he said, 'Look, you don't want to be  years old and look back and ask yourself ... why didn't I do this? Why didn't I try it?" Cuban says.
"For me, the best way to think about it was to project myself forward to age 80," Bezos says. "When I'm 80 years old, I want to have minimized the number of regrets that I have. I don't want to be 80 years old, in a quiet moment of reflection thinking back over my life, and cataloging a bunch of major regrets.
"In most cases, our biggest regrets turn out to be acts of omission," he continues. "It's paths not taken."
That convinced him to take a risk and start Amazon, which now has a market cap of over $550 billion and has made him the richest person in the world.
"I decided I had to give it a shot," Bezos says in a 2010 baccalaureate address at Princeton. "I didn't think I'd regret trying and failing. And I suspected I would always be haunted by a decision to not try at all."
Cuban, worth $3.3 billion, agrees that pushing himself to experience new things has been worth it.
"Maybe it will come back to haunt me, all the fun I've had, but I've had fun," he says.
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