Mike Stone/Reuters
Before becoming even moderately successful, he was a recent college graduate sleeping on the couch (or floor) in a crowded apartment who decided to build a business after getting fired from his job.
Through his journey to success, with all the ups and downs that come with it, he's realized what works and what doesn't.
In his book "How to Win at the Sport of Business," he outlines the "Twelve Cuban Mantras for Success," which we've summarized below.
1. Time is the greatest asset.
"How wisely you use your time will have far more impact on your life and success than any amount of money," Cuban writes.
He started his first company, software distributor MicroSolutions, when he was 25 and had no money. After it became modestly successful, his secretary embezzled and ran away with $83,000 of the company's $85,000. Rather than give up and try something else, Cuban writes, he studied PC software and coding relentlessly to gain an edge over the competition. He ended up selling MicroSolutions to H&R Block for $6 million in 1990.
2. It's worth being nice to people.
"Being successful entails being able to not only get along with people, but also to give something back," Cuban writes.
When the committee behind Dallas' beloved St. Patrick's Day Parade almost canceled the event after its largest sponsor pulled out in 2012, Cuban donated $40,000 to keep it afloat, adding an additional $25,000 to the committee's fund for local schools. Beyond being a generous gesture to the community, it also won Cuban goodwill and an ongoing outlet to promote his basketball team and investments.
3. "No balls, no babies."
"This is something a blackjack dealer once told me when I asked him if I should hit or stick," Cuban writes. "It is also my favorite line and probably the thing I tell myself the most. Once you are prepared and you think you have every angle of preparation covered, you have to go for it."
4. If you don't set aside time to have fun, your work will suffer.
It's understandable if you're a new entrepreneur who is foregoing vacation time to get your business to scale - Cuban says he went seven years without one when he started - but you need a way to unwind or you're not going to perform to your full potential, he says.
Cuban says his party days are behind him, but he still likes to "blow off steam" with pickup basketball games nearly every week.
5. You can change fear from an impediment to a motivator.
When adrenaline flows through your veins when you're confronted with a crisis or significant challenge, you can frame that rush with an anxious mindset or a determined one. Use that fear to become more competitive, Cuban says.
And if you fail, you'll realize that your life will continue. "I've been fired from more jobs than most people have had!" Cuban writes. But he kept trying anyway.
6. Always be ready for the unexpected.
It's a form of preparation to realize that there are some things you can never see coming, Cuban says. With that understanding, you can prevent yourself from becoming impulsive when events take an unexpected turn and then take advantage of an opportunity others are ignoring.
7. Yelling is OK!
"If someone believed strongly enough in something and I was being passionate about something, I wanted them to match my level of passion," Cuban writes. "So I told people that if they thought it was the only way to get through to me, go for it!"
He does note, however, that while open communication is best at every workplace, yelling may not be.
8. There will be times when you're down, but you'll be judged by how quickly you rebound.
"I can't count how many times I have gotten up in the morning dreading the day," Cuban writes. "EVERYONE goes through those moments," but it's the ones who fight through them the quickest, having learned something from the experience, that become truly successful.
9. "It's not whether the glass is half empty or half full, it's who's pouring the water."
Cuban says that he uses this twist on a common maxim to remind himself that while there will always be unpredictable events affecting him, he is ultimately responsible for his success and happiness.
And that means always striving to gain control of the game so that the competition plays by your rules.
10. Aspirations that aren't acted on are meaningless.
Cuban believes that anyone with dreams can become successful, but that most people keep their goals hanging over their heads.
"When I catch myself daydreaming about how I'm going to do this or that, I always try to wake up and ask myself just how I'm going to get from where I am to where I want to be," he writes.
11. "Pigs get fat; hogs get slaughtered."
Cuban says he first heard this from his business partner Todd Wagner. Making a deal in business is an art, and those whose egos make them too greedy miss out on potentially valuable relationships.
"Every good deal has a win-win solution," Cuban writes. He respects ambition but says "there is nothing I hate more than someone who tries to squeeze every last penny out of the deal." He explains that he's done deals with people who aggravated him so much in the negotiation process that he could never fully trust them and ended up ending the partnership.
12. It only takes one win to become successful.
"The beauty of success, whether it's finding the girl of your dreams, the right job, or financial success, is that it doesn't matter how many times you have failed, you only have to be right once," Cuban writes.