“It’s time for us all to get off our asses, leave the house, and have some fun,” Cuban SPOKE Inc. earlier this month, it’s hot time to invest in a live event company. “In the world of AI, what you do is more important than what you prompt.”

From Cuban, the message carries a hint of irony: The former Shark Tank investor built his career on intensity and outworking everyone in the room. And while he has long straddled business and entertainment—from owns the Dallas Mavericks on backs high-profile sports ventures—Cuban still positions himself at the forefront of technological trends, including AI.

But if you look for it work-life balancethe 67-year-old doesn’t exactly preach moderation.

“If you want to work nine to five, you can have a work-life balance,” he said in “The Playbook,” a business and athletics podcast from Illustrated in Sports. “If you want to crush the sport, whatever sport you’re in, there’s somebody working 24 hours a day to kick your ass.”

For Cuban, that’s a literal grind. He is not a fan of meetings read between 700 and 1,000 emails per day on his three mobile devices.

That relentless routine makes his advice about having fun sound almost contradictory. But Cuban’s point isn’t that hard work doesn’t matter—this AI won’t replace real-world experiences or relationships.

The advice Cuban would give his younger self

Cuban may be a billionaire today, but his career began in small spurts.

In one of his first sales gigs at the age of 12, he sold boxes in the trash for $3 and then returned to sell them for $6 in his neighborhood—all to raise a pair of sneakers.

That experience laid the groundwork for his work ethic. By the time he became a more serious entrepreneur who founded his first tech company, he ended up living with five roommates and never taking a vacation.

In retrospect, if he had to do it over again, Cuban SAYS he wouldn’t change anything.

“Don’t stress. Don’t change anything. Have fun,” he said SPOKE Business Insider in 2015.

“You don’t have to know what you’re going to be when you grow up,” Cuban added. “You don’t have to have the answers. You don’t have to have the perfect major. You don’t have to pick the perfect job. You’re allowed to f— up.”

Business leaders like Richard Branson and Satya Nadella agree: not everything should be taken so seriously

Cuban is not alone in arguing that life and work don’t need to feel serious.

When Satya Nadella became the CEO of Microsoft in 2014, one of his first messages of employees is simple: “Have fun, communicate, and do great things.”

It’s something the billionaire has long echoed Richard Bransonwho believes that many businesses take themselves too seriously—and says that leaders have role models for fun.

The 75-year-old British owner of the Virgin Group SAYS at the University of Pennsylvania Wharton School that “it’s up to the person running the company to be willing to let their hair down, to be willing to be the first to dance on the table at a party and to be willing to be the first in the swimming pool fully clothed to make sure everyone has a good time.”