I suspect people who transition from working class (and I mean it in a sense that you have to work to earn an income to keep a roof over your head, be that $30k/yr or $300k/yr) to capital class (meaning their assets fund their dynasty without sweat, in good times and bad, $100m+ type people) struggle to realise what it actually means to not have to worry about money, and that money is just a way of keeping score.

Likewise a lot of the wealthy people have no real concept of the fact if you don't work, you don't eat. Maybe you've got savings that tide you over for a year or two, or even a 401k that keeps you going for the rest of your life, but that's not really the same thing.