Its funny, I went to a private high school which was filled with kids like this, sons and daughters (lol) of top executives of Companies like AOL during its prime, and even members of The Marriott family, But whats interesting is that the ones with the MOST money were usually the ones who least flaunted it.
I think of one of my dad's friends, not going to name names but he is one of the richest men in Egypt/middle east, sure he has rich people toys and a masssssssive yacht (I've stayed on it) which he charters and rents out to celebrities....and I'm not talking B listers, I'm talking Madonna and Jennifer Lopez (to name a few)..... but this guy is one of the nicest most humble human beings I've ever met. If you just saw him standing on a street you wouldn't think anything of it... he doesn't dress flashy or extravagent, wears a simple $50 watch, very easy going and the people who work for him absolutely love him.
Nothing wrong with being rich and enjoying it (I think that's what we all strive for) but flaunting it all the time like a douche bag tends to show that there is some type of insecurity and a deeper issue in my opinion.