Trump has been not been a successful businessman, Consider this:
Trump’s net worth has grown about 300% to an estimated $4 billion since 1987, according to a report by the
Associated Press. But the real estate mogul would have made even more money if he had just invested in index funds. The AP says that, if Trump had invested in an index fund in 1988, his net worth would be as much as $13 billion.
http://fortune.com/2015/08/20/donald-trump-index-funds/
In other words if he had done nothing but invest his inheritance in index funds he would worth a lot more than he is now. These numbers represent the litany of failures that Trump has done over the years. Trump is not really an entrepreneur, he is a dilettante playing with his inheritance money. He is no Warren Buffet or Bill Gates.
So what "skill set" are we talking about here? Show biz skills? The ability to project an image that bears no resemblance to reality? The problem with that is that people see through it eventually, and then they realize this emperor truly has no clothes.