Trump is not an entrepreneur in the sense that he has done anything new, innovative, or particularly useful. Casinos are counterproductive to society. He is simply a huckster, a promoter, and he has a huge ego and feels this compulsion to be Number One.
A lot of his schemes have flopped. He has usually managed to leave others stuck with the losses. He is ignorant of both the political system and foreign policy and would be a horrible disaster as president.