Mark Cuban reveals $125k purchase he made after drunk phone call when he sold his first company

Billionaire entrepreneur and investor decided to buy a lifetime pass with American Airlines after a drunken night with friends

Upon selling his first company for $6 million in 1990, entrepreneur Mark Cuban could be forgiven for wanting to make some expensive purchases.

But it was a night out with friends and a drunken phone call that led to a rather unusual buy - a $125,000 American Airlines lifetime pass.

Cuban, 66, told Shannon Sharpe last week on Club Shay Shay that he was the proud owner of the AirPass which gives a flyer top-tier benefits and essentially unlimited miles to fly first class anywhere.

Mark Cuban, the billionaire investor, said he purchased an American Airlines lifetime pass when he sold his first company (Club Shay Shay / YouTube)

He said he chose to invest while getting “destroyed” with his buddies at a steakhouse. Cuban’s friends asked him what he planned to do with the money he obtained from selling his first company, MicroSolutions.

“I don’t care about cars or houses but boy, you know, I fly a lot for work,” Cuban said. “If I could get this lifetime pass – I wonder if such a thing exists?”

Moments later, drunkenly Cuban said he called American Airlines and asked if they sold lifetime passes, which they did.

“They’re like ‘Let me connect you to the Airpass department.’ I’m like ‘What!’” Cuban recalled. He said he hung up the phone before he could purchase it in the moment.

“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 said.

With adjustments for inflation, the Airpass Cuban bought would cost around $300,000 today.

“I’d be out in LA or wherever, Dallas, and I’m like ‘Want to go on a road trip? Let’s call American Airlines and see if they got any flights tonight. Let’s go to Vegas. What’s your name again? Doesn’t matter. Let’s go to Vegas,” Cuban said.

While the Shark Tank investor got some use of it, he said he eventually transferred it to his father who had it until his death. Then Cuban gifted it to a friend.

Cuban sold MicroSolutions in 1990 for $6 million (AFP via Getty Images)

He seemingly had no use for the pass once he amassed a fortune, estimated to be around $5.7 billion, per Forbes, to buy a private jet. He told Sharpe he spent $40 million on a G5 jet after he protected his $1.4 billion in Yahoo stock from the 2000 stock market crash.

The Airpass program debuted in the 1980s, offering members unlimited first-class travel for the rest of their lives. American Airlines stopped offering passes to new members in November 2022 and fully concluded the program in March 2024.

However, members with current contracts are permitted to use it until it expires.