After selling his first startup MicroSolutions to CompuServe in 1990, a 32-year-old Mark Cuban celebrated in his own unconventional way. Instead of splurging on luxury cars or real estate, he picked up the phone, hungover  and called American Airlines to ask if they sold lifetime flight passes. “They did,” Cuban later recalled on the Club Shay Shay podcast. “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 g ...