When the people who work for the $billionaire stop working for him, he fails. Why? He doesn't have enough practical experience doing things for himself to know how to do them... because he has had others do the things for him.
Reality check, they don't quit because they need money for survival so the rich get to richer and it goes on forever unless the billionaire himself sets him to lose all money on something that has a success rate of 100% being a failure.