Mark Cuban didn’t wait long to splurge after his first big pay day.
The now billionaire bought a lifetime flight pass from American Airlines for six figures while drunk and celebrating his first big deal back in 1990, Cuban explained to host Shannon Sharpe on the “Club Shay Shay” podcast in an interview released last week.
When the “Shark Tank” star sold his first company, a software startup called MicroSolutions, to CompuServe for $6 million, the freshly minted millionaire entrepreneur celebrated by getting sloshed with friends.
“They’re like, ‘What do you think you’re going to do with all this money?’ And I’m like, ‘I don’t care about cars or houses, but boy, you know, I fly a lot for work,’ ” he recalled to Sharpe.
Cuban called American Airlines while slurring his words and drunkenly asked if they offered a lifetime pass – they did.
“I got all that information, hungover as hell, and I signed up. Initially, it was $125,000 and then I upgraded it. I forget how much I paid, but it gave me almost unlimited miles for me and somebody else for the rest of my life,” Cuban told the ESPN personality.
Cuban bought the AAirpass, which launched in the early 1980s and gave flyers unlimited first-class travel for the rest of their lives. Back then, the price was based on the buyer’s age at the time of purchase.
It was the 1990s and the entrepreneur was only 32 years old when he bought it so the pass cost $125,000, which is estimated to be around $300,000 when adjusted for inflation.
Cuban reportedly transferred the pass to his dad and after his father passed away, he transferred the AAirpass to a friend.
Unfortunately, American Airlines no longer offers this unlimited pass.
The airline eventually discontinued the offer and started charging a flat rate for frequent business travelers until recently,
American Airlines stopped accepting new Airpass memberships and renewals in 2022 and closed the program in March 2024, according to its website.
This unlimited flying pass wasn’t the only splurge the businessman made.
In 1999, Cuban also bought a $40 million Gulfstream G5 jet on the internet after selling his streaming platform Broadcast.com to Yahoo for $5.7 billion in stock, according to CNBC. That massive deal is still listed on the Guinness World Records’ website as the “largest single e-commerce transaction.”
Despite his pricey record-setting purchases, Cuban told listeners of the podcast that he encourages people to live like a “college student” and save their money – especially athletes, because if they got injured the money stops pouring in, fast.
Cuban still finds ways to stay grounded. In 2017, he told Money that even though he could enjoy a lot with his fortune, he’s still lived in the same house for 18 years and drove the same cars.
