I worked for a trust fund kid. It started off great until I realized he had no understanding of how money worked. Despite him saying / thinking he cared about the bottom line and the well being of the company, he really only cared about his ego and if his (rich) family thought he was successful.
I worked for a guy who was given his family's company. When I told him my 4th birthday was approaching he tried to relate to me by asking if I was getting a boat over 40 ft because "a man's age should never be less than his age.". Because not only did he think I had a massive boat, he also thought I would buy a new one as I grew older.
This guy also refused to hire actual employees if he didn't have to. Everyone was "temp".