I think the issue here is that with retirement levels of money existing friendships can become strained.
If your high school friend earns 50k a year and you earn 100 then I mean sure, you have different toys, bigger house, whatever, but you're both existing in the same universe with similar constraints.
If your high school friend earns 50k a year and you suddenly have 60 million like the guy in the post then it's more of a test because your lifestyle can just differ hugely.
Some people can handle it but with others there will be an underlying resentment. There are lots of layers to it. They look for work - you look for suitable employees.
Having said that, in my experience there are only really a few major cut-offs, one between homeless/terminally skint and working, one between working and being able to live off of investment income, _maybe_ one at the sort of bodyguard required super famous level. Inside those it's just sort of like, yeah ok, your car/yacht/jet/whatever is better than mine, cool.