I don't doubt his intelligence, actually. His mother seems pretty smart, tbh, even if she's an angry, abusive person. It's not that he isn't smart, per se, but rather how he chooses to use it and where he gets his "facts" to base his decisions. I think that with better advice and education in business he would actually make more "intelligent" appearing decisions, but he is very young and easily influenced.
I guess it comes down to how his moral compass works. If he thinks, I am in demand, therefore I can ask for more with little consequence (solid contract if they say no, prospective pay increase if they say yes), then why is it dumb to push the issue? If you take a step back and think with less ego, you might start to reflect on your public image, or how people perceive your move.
In the end, I think this is pretty much how businesses operate: how can I make more money, and what position am I in to squeeze more profit? Nestle has a shit reputation, but avoiding their products is hard for the average person, and so they continue to earn even when they're
shown to be raping the planet.