I don't have much time for people who are jealous of the "playboy" image. He's earned the money (ok, inherited the family firm, but he's worked hard to keep it earning money - it's not always a given, when son takes over from father, that son has the same business drive as father), so he can spend it how he wants.

As for the obnoxious - successful people do tend to be very sure of themselves - that's what makes them successful.