Trump isn't a billionaire because he had "what it takes to be successful" so don't make me laugh. He's a billionaire because he inherited his wealth from his father. Every businessperson does not play by the same rules because the super rich have a much greater ability to avoid paying their rightful share of taxes because they have paid lobbyists who "pay" politicians to write tax laws in their favor. The average working person does not have such a favored ear with members of Congress who write tax laws. 
It doesn't matter if Trump saw a homeless man on the street and remarked in a particular year that the homeless man was worth more than he was since, as everyone knows and Trump knew at the time, he still had a great deal of wealth. 
The biggest problem with Americans is there are so many loathsome sycophants willing to do the dirty work of the super rich. Too bad taxation is the substitute for the guillotine, such bootlickers deserve to lose their heads.