Was F. Scott Fitzgerald's "Gatsby" right about the rich being "different from you or me"?

Not necessarily. There are plenty of wealthy people on the West Coast who are clotheshorses, because they want to be. To them, that’s one of the things that money’s for. Or because they have an image to maintain, so it’s an obligation to wear the newest latest. And on the East Coast, if we’re talking Old Money in New England and certain places in New York state, those people often dress casually because they don’t have to prove anything.

(A certain kind of casual, mind you. I remember the Official Preppy Handbook describing go-to-hell pants and the go-to-hell blazer, and concluding, “There is not a go-to-hell shirt.”)

My father grew up rich in the 30’s (hired help around the house, nanny raised him). He never developed the work ethic. Once that money didn’t trickle down to him, he never found a way to work and make money and be happy. He was obsessed with get rich quick schemes and wanted to simply invest his way to wealth. He job hopped and started a few businesses, but he told me on more than one occasion that “hard work is for suckers”. Thank goodness my mother instilled work ethic in me.

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There was a recent thread on the “Worst wedding announcement ever” drawn from the NYT’s “Society” pages. If you read stuff like that - and you won’t be able to for long - the unadulterated douchbagginess of the generationally rich is just astounding. It drips from them. People who BECOME rich can get pretty bad, but not necessarily, and most remain reasonably decent human beings.
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Depends on what you define as generationally rich. I’ve dealt with quite a few and the children of rich people tend to fall into two categories; the daddy made money, nouveau riche, who certainly qualify for what you say and old money who generally don’t. Individual milage may vary of course.

Old money seems to me to be different from everyone else in one major way. Middle-Class people know stuff, these old money types know people. You can mention anyone and they have direct or indirect connections to them. You vote for the PM, they play golf with him and are besties with members of his staff. And that make all the difference.

Pretty much anything they need to do, can be done with a phone call to the right person. From the small. Tickets to a hard to get play/musical? Well they donate to the theatre and the owner is too happy to oblige. To the big. They need to convince a large cooperation to invest in their son’s start up? Ask the CEO who is an old friend to take a look. (Thats how Bill Gates got his shot with IBM signing on Microsoft).

There is also a big difference between “rich people” and “people with a lot of money”. The latter can live lives of comfort and spend money on frivolous things and get noted. The former see their fortunes as bedrock for their own endeavours; and to mitigate risk. Lets start the new business, worst case scenario it fails; they are not going to starve.

There is a reason that mostentrepenuers come from wealthy families.

One of the best examples of how the generationally rich (old money types) are different from the newly rich who made a fortune is in Jeffery Archer’s Kane and Able. The contrast between the two men, billionaires (inherited and self made-sort-of) is stark. Every choices they make is informed by that.

Nouveau riche made their own wealth. The only thing old money did was pick the right parents to be born to. Everything else is just trying to appear better than everyone else to justify their existence.