Mark Cuban drunkenly called American Airlines after selling his first company—and bought a lifetime flight pass for $125,000

Some people send risky text messages or go sing karaoke after having a few drinks with friends. Entrepreneur and investor Mark Cuban took it a few steps further, spending six figures to buy a lifetime flight pass.

It was 1990, and Cuban — age 32 at the time — had just become a millionaire by selling his software startup MicroSolutions to CompuServe for $6 million. “My buddies and I went out and just got destroyed,” he told the “Club Shay Shay” podcast last week. “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.'”

Cuban didn’t know if lifetime flight passes even existed, he said, but he grabbed a phone and dialed up American Airlines anyway.

“I called them up and just slurred my words, ‘Do you guys sell lifetime passes?'” said Cuban, now 66. “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.”

The AAirpass, which debuted in the early 1980s, gave members unlimited first-class travel with the carrier for the rest of their lives — for a price that depended on their age at the time of purchase. In Cuban’s case, his $125,000 in 1990 would be worth roughly $300,000 in today’s dollars when adjusted for inflation.

In 1994, American Airlines replaced the AAirpass with a similar membership, Airpass, which offered fixed-rate flights for frequent business travelers. The airline halted new memberships and renewals in November 2022, and stopped honoring the Airpass’ unlimited travel perks in March 2024, according to its website.

In the years after buying his AAirpass, Cuban shared his flight privileges freely: “I’d be out in LA or Dallas like, ‘You want a road trip? Let’s call American Airlines.'” He eventually transferred it to his dad — and later, after his dad died, to a friend, he added.

After all, in 1999, Cuban made another impulse purchase. Newly minted as a billionaire after selling his audio streaming platform Broadcast.com to Yahoo for $5.7 billion in stock, he bought a $40 million Gulfstream G5 jet. The transaction still holds a Guinness World Record for most expensive e-commerce transaction ever.

“[Buying a plane] was my all-time goal because the asset I value the most is time, and that bought me time,” Cuban told Money in 2017. “Other than that, I’ve lived in the same house for 18 years and still have the same cars.”

“Other than the plane, which is a big splurge, I’m still a slob. Not all that much has changed,” he added.

Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank,” which features Mark Cuban as a panelist.

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