I grew up surrounded by rich ~~assholes~~ people, and can anecdotally confirm that a lot of them, especially those born in it, live in a parallel world, so far removed from the average person's lives that they just can't relate, even if they try very hard. So few of them even seem able to (or want to?) realize how much of a kickstart they had in life just by being born in the right family, how much liberty they had having the opportunity to fail without ruining themselves.

We weren't private jet rich, but still, we went on family trips more often than my friends, had a big house, parents had nice cars, we partook in expensive competitive sports such as golf/tennis/ski, etc... Despite having pretty grounded parents, who taught us very young about how unconventional our lives were, I still severely underestimated the value of money in this world. I had a rude awakening when I met my now wife, who grew up in a much poorer environment. I cut contact with pretty much everyone from my childhood neighborhood.