People have moments when they splurge a little after a success, but for billionaire Mark Cuban, a night of celebration after selling his first startup led to a life-changing purchase.
While sharing his story on the “Club Shay Shay” podcast, Shark Tank‘s famed judge recalled the celebratory night, stating, “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.’”
In a tipsy moment, he dialed American Airlines, slurring his words as he asked if they offered a lifetime flight pass.Much to his surprise, they did.
In 1990, fresh from selling his software company MicroSolutions to CompuServe for $6 million, a 32-year-old Cuban found himself celebrating with friends in an unusual way. Instead of fancy cars or luxury homes, he made a late-night call to American Airlines — and walked away with a lifetime flight pass.
After sobering up, Cuban followed through on the deal, purchasing the pass for $125,000 — a sum that would be worth around $300,000 today. “I signed up, hungover as hell… it gave me almost unlimited miles for me and somebody else for the rest of my life,” he shared during the interview.
The AAirpass, which was launched in the early 1980s, allowed unlimited first-class travel for life. Cuban made full use of it, generously offering trips to friends and even transferring the pass to his father before eventually passing it on to a friend after his dad passed away. Unfortunately, American Airlines discontinued the AAirpass program, ceasing renewals and new memberships in 2022, and bringing it to a complete close in 2024.
This wasn’t Cuban’s only major splurge. In 1999, after selling his next company, Broadcast.com, to Yahoo for a whopping $5.7 billion, Cuban bought a $40 million Gulfstream G5 jet. The transaction still holds a Guinness World Record as the largest e-commerce deal ever.
“Other than the plane, which is a big splurge, I’m still a slob,” he told Money in 2017, noting that he’s lived in the same house for 18 years and drives the same cars.
Cuban also advised others on the podcast. “Live like a college student,” he urged people, particularly athletes who face uncertain financial futures due to potential injuries.