In reality all he has are street smarts, a collection of miscellaneous bits of procedural knowledge, and several half baked stacks of business self-help tidbits. He makes many mistakes but never owns up to them, passing over them impatiently and reasserting his arrogance on the next subject. He has managed to build a company over the last twenty years, loosely following emerging trends and emulating entrepreneurs around him, and this is something, at least to him. He has the gall to bully people into subordinate positions and manipulate them to suit his ends, which has worked out for him. At least he can buy his iPads and watch his favorite reality TV shows and vote Republican to preserve the empire he has built all by himself, no thanks to the multitudes of morons and incompetents that have worked for him.
He is classically American. And he has no idea how small his world is.