Mark Cuban's childhood was "as middle class as you can get," he told Dale Hansen on Dallas News channel WFAA.
After graduating from Indiana University, he said, he set off for Dallas, moved into a three-bedroom "dump" with five friends, and worked as a bartender to make ends meet.
Cuban earned his first million by age 32 when he sold his first company, MicroSolutions. Less than 10 years later, he sold his second company, Broadcast.com, to Yahoo for $5.7 billion and became a self-made billionaire at age 40.
It's safe to say the "Shark Tank" investor and Dallas Mavericks owner is set when it comes to money — but how much money does he think is "enough"?
"'Enough' is what it takes to not worry about the bills," Cuban said in his debut monthly column in the October issue of Men's Fitness. "'A lot' is enough that you never have to worry about working again."
But it doesn't stop there. "'F you' money means you can rent a jet to go wherever you want, whenever you want, and no party is out of reach," the billionaire explained.
"'F everyone' money means you can have your favorite band in your backyard, not care how much it costs, and lend them your jet to get there."
Cuban seems squarely in that latter category and is loving every minute.
When Men's Fitness asked about his smartest purchase, he answered, "A plane." When asked about his dumbest, he said, "Let's see. ... If I could remember them, I could list you a couple hundred bar tabs with my buddies."
Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."