It was all working according to plan for Mark Cuban. He had sold his first business, MicroSolutions, in 1990, retiring handsomely rich at age 29. He bought a lifetime, fly-anywhere-with-a-friend forever pass from American Airlines and had envisioned an immediate future of reasonable if dedicated debauchery. The plane-and-party proposition gained some altitude, but as sometimes happens, a woman kept diverting him back to his adopted hometown of Dallas.
“I was having a blast. But there is always that girl who gets in the way,” Cuban told me via email, a medium in which he is famously responsive. Pity that romance didn’t work out, but then again, spending more time in Big D to be near “that girl” would lead to him cofounding, with Todd Wagner, Audionet in 1995, just as…