Jaimie Johnson who filmed the documentary Born Rich (and its sequel) pissed off enough of his family and peers that he was almost thrown out of high society for exposing its underbelly. He also lives a pretty normal life echewing his family fortune which is pretty dope. Might be along the lines of what you’re looking for. Good films either way.

ETA check out The One Percent as well, his follow-up from the first film.