After selling his first company, Mark Cuban purchased a lifetime flight pass from American Airlines for $125,000.

Mark Cuban, an entrepreneur and investor, spent six figures to purchase a lifetime flight pass.

In 1990, Cuban, who was 32 years old at the time, became a millionaire by selling his software startup MicroSolutions to CompuServe for $6 million. He recounted his experience on the "Club Shay Shay" podcast last week, saying, "My buddies and I went out and just got destroyed. 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.'"

American Airlines was contacted by Cuban despite his uncertainty about the existence of lifetime flight passes.

"Cuban, now 66, recounted how he called up the company and slurred his words, asking about lifetime passes. Despite being hungover, he obtained the necessary information and signed up, initially paying $125,000. He later upgraded and cannot remember the exact cost, but the pass granted him almost unlimited miles for himself and someone else for life."

The AAirpass, introduced in the early 1980s, granted members unlimited first-class travel with the airline for life, with the cost depending on their age at purchase. For Cuban, his $125,000 purchase in 1990 would be worth approximately $300,000 today, adjusted for inflation.

In 1994, American Airlines introduced a membership program called Airpass, which offered fixed-rate flights for frequent business travelers. However, the airline stopped accepting new memberships and renewals in November 2022 and stopped honoring the Airpass' unlimited travel perks in March 2024, as stated on its website.

After purchasing his AAirpass, Cuban would often offer his flight privileges to friends and family, saying, "Want to take a road trip? Let's call American Airlines." He eventually transferred it to his father, and after his father's passing, he passed it on to a friend.

In 1999, Cuban made another impulse purchase after becoming a billionaire by selling his audio streaming platform Broadcast.com to Yahoo for $5.7 billion in stock. He bought a $40 million Gulfstream G5 jet, which still holds the Guinness World Record for the most expensive e-commerce transaction ever.

"Time is the asset I value the most, which is why buying a plane was my all-time goal," Cuban said in 2017. "In addition to that, I've lived in the same house for 18 years and still have the same cars."

"While the plane was a significant expense, I'm still a slob. Not much has changed," he remarked.

Mark Cuban is a panelist on "Shark Tank," which CNBC owns the exclusive off-network cable rights to.

To become a successful and confident communicator, enroll in CNBC's online course, "Become an Effective Communicator: Master Public Speaking." Our program will teach you how to speak clearly and confidently, manage your nerves, choose the right words, and use effective body language to make a great first impression. Sign up now.