And in order to keep the cash flowing, Cuban admitted he had to take on some unusual side jobs — some more notable than others.
"I just did everything," Cuban told sports radio talk show host Jim Rome, 54.
During his high school and college years, Cuban said he was a stock clerk, working at a grocery store called Gracie's, as well as Isalys in Pittsburgh.
"In Pittsburgh, there's a local delicacy called 'chipped chopped ham,' and so like, the first week I'm working there I'm slicing ham and I wasn't paying attention and literally I sliced off the tip of my second finger. It's just like blood everywhere!" recalled Cuban, noting that it — fortunately — didn't do any "real damage."
The businessman also said he paid for his junior year at Indiana University, where he transferred after wrapping up his freshman year at the University of Pittsburgh.
But Cuban said his favorite "side hustle" was probably teaching disco lessons during college.
"By the way, the disco lessons ... was that to help pay for college or did you do that to meet chicks?" Rome joked.
"All of the above. I mean, literally, I got paid $25 an hour back then to teach dancing to sororities. It was the best job ever. I mean, $25 an hour, are you kidding me? I'd take that job now," Cuban added.
"Dude, that is so much money," agreed Rome.
Cuban, who is now worth an estimated $4.1 billion, has been candid about his past financial struggles over the years.
“When I was broke and sleeping on the couch, I couldn’t open up a bank account. You needed to have 200 bucks. You needed this, you needed that. They didn’t give me one,” Cuban recently revealed on an episode of "Shark Tank," per CNBC.
After graduating from Indiana in 1981, Cuban reportedly only had $60 in his pocket.
“I had quit or been fired from three straight jobs,” admitted Cuban, who said he luckily soon found his love of tech shortly after, according to CNBC.
“When I got one of my first jobs out of school using technology, it was like, wait, I love this. I’ve taught myself the program, I could go seven hours, eight hours without taking a break thinking it was 10 minutes because I was concentrating so hard and so excited and really loved it. And that’s when I realized that I can be really, really good at technology," he added, noting his hard work paid off, leading him to his first business MicroSolutions.