Jaimie Johnson who filmed the documentary [Born Rich](en.m.wikipedia.org/wiki/Born_Rich_(2003_film) (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.