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PulseReporter > Blog > Money > Mark Cuban didn’t take holidays for practically a decade—the billionaire had 5 roommates and labored weekends to show his profession round after getting fired
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Mark Cuban didn’t take holidays for practically a decade—the billionaire had 5 roommates and labored weekends to show his profession round after getting fired

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Last updated: June 16, 2025 4:11 pm
Pulse Reporter 2 weeks ago
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Mark Cuban didn’t take holidays for practically a decade—the billionaire had 5 roommates and labored weekends to show his profession round after getting fired
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  • Billionaire investor Mark Cuban didn’t take a trip for seven years when he first constructed the $30 million-a-year tech firm MicroSolutions. On the time, he was “broke as f-ck,” just lately fired and residing with 5 males in a three-bedroom condo. However working onerous at a younger age paid off. Cuban is in the present day price $5.7 billion—and it’s a piece philosophy he now recommends.

Most individuals of their 20s have already got their weekends booked out for bar hopping and hanging with mates, however one CEO lived a really completely different life in his youth. When billionaire entrepreneur Mark Cuban launched his first expertise firm at simply 24, journeys to Bora Bora weren’t on the desk.

“[I] didn’t take a trip for the subsequent seven years,” Cuban mentioned in an interview with Sports activities Illustrated’s sequence “The Playbook” on June 3. “I used to be broke as f-ck, the place else was I going to go?”

Right this moment, Mark Cuban could also be sleeping in a $25 million, 24,000-square foot mansion in a rich Dallas neighborhood. However within the Nineteen Eighties when the 66-year-old former Shark Tank investor first launched MicroSolutions, a software program enterprise additionally offering pc consulting companies, he had simply been fired from his job. At the moment Cuban was sharing a “nasty” three-bedroom condo with 5 roommates, the place he usually slept on the ground.

“I used to be residing, six guys in a three-bedroom condo, which wasn’t nice. It was a sh-thole,” Cuban mentioned.

However experiencing all-time low lit the match to lastly make investments all his time into constructing his expertise enterprise right into a million-dollar success. With no 9-to-5 to report back to or a monetary security blanket to again him up, Cuban made it his mission to work night time and day till the enterprise took off.

“If I took the weekend, the entire thing might fall into the sh-tter,” Cuban defined. Throughout these seven years with no days off, he mentioned MicroSolutions climbed to over $30 million in gross sales, ultimately being offered to H&R Block for $6 million. 

Cuban’s recommendation for younger individuals: ‘Work your ass off’ and be taught whilst you sleep

The entrepreneur price $5.7 billion has at all times given recommendation that younger individuals ought to have an intense work ethic to propel them to success. And within the new period of AI, Cuban mentioned that teenagers ought to even be studying of their sleep. 

“If I used to be 16, 18, 20, 21 beginning in the present day, I’d spend each waking minute studying about AI,” Cuban mentioned at SXSW earlier this 12 months. “Even when I’m sleeping, I’m listening to podcasts speaking about AI.”

“These individuals who put within the time are going to crush it.”

In March, Cuban even rolled out a chatbot with MasterClass on Name so customers can ask AI-Cuban questions and for recommendation on emulating his success. At anytime, day or night time, individuals can subject concepts and points by the instrument. When Fortune requested the chatbot questions—like the way to make your first million {dollars}—it echoed the identical philosophy Cuban has been espousing for years.

“Work your ass off, be taught the whole lot you may, and keep adaptable,” Cuban’s AI chatbot responded. “Success hardly ever occurs in a single day, however persistence and sensible choices can get you there.”

This story was initially featured on Fortune.com

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