Hilton CEO Chris Nassetta says selling his black Porsche 944 was the best financial decision he ever made.

That's because buying it in the first place was his worst. He was in his 20s and fresh off a breakup when he saw the sleek model in a used car lot near his home in Arlington, Virginia. He had a third party ensure the car and the deal were legitimate, then paid $20,000 for it, taking out a loan to cover part of the cost.