Trump has more understanding and insight than his opponents realize. For a man such as Trump to risk acquiring so many powerful enemies and to risk his wealth and reputation, he had to have known that the people's dissatisfaction with the ruling establishment meant he could be elected president.
The great problem with corporate capitalism is that publicly owned companies have short time horizons. Unlike a privately owned business, the top executives of a publicly owned corporation generally come to their positions late in life. Consequently, they have a few years in which to make their fortune.