In 1990, fresh off selling his first company for $6 million, entrepreneur Mark Cuban made an impulsive yet legendary investment after a night of heavy celebration.

Rather than splurging on cars or houses, Cuban decided to secure a lifetime of air travel-an impulsive decision that has become part of his legacy.

After selling his software startup, MicroSolutions, Cuban and his friends went out to celebrate. In a haze of excitement and alcohol, Cuban had one thing on his mind: flying.

Not knowing if such a thing existed, he called American Airlines late that night and slurred, “Do you guys sell lifetime passes?” To his surprise, they did.

Cuban purchased an AAirpass for $125,000, which gave him and a guest unlimited first-class travel with American Airlines for life.

Adjusted for inflation, the cost today would be roughly $300,000. Cuban upgraded his pass over time, and for years he generously shared his flight privileges with friends and family.

Eventually, he transferred the pass to his father, and after his father passed, to a close friend.

Cuban’s Ultimate Splurge

While the AAirpass was one of Cuban‘s early indulgences, it wasn’t his last.

In 1999, after selling his second company, Broadcast.com, to Yahoo for $5.7 billion, he made another life-changing purchase-a $40 million Gulfstream G5 jet, which still holds the Guinness World Record for the most expensive e-commerce transaction.

For Cuban, the jet wasn’t just a luxury-it was a way to save time, his most valuable asset.

Despite his big purchases, Cuban insists that little has changed about him over the years, saying, “Other than the plane, I’m still a slob. Not all that much has changed.”