I may qualify.

We lived in a few different areas, Dad went wherever the money was, but it was always in a big house in the nicest suburb. Private schools, country clubs, ski trips, vacation houses. Rich personal and family friends. I was the neighborhood lawn mower/pet sitter, everyone had big lawns and multiple pets so it was decent money for a teenager.

Went to a top 10 university on scholarship. Majored in engineering, as Dad did.

My problem is that I'm a lousy interviewer. Even trying to compensate for this fact I suck at it. My success rate since college is something like 2 for 50. One of them was just a bunch of math questions.

Worked for my dad for awhile but eventually moved out to a large city. For a few years I had wildly fluctuating income, like between $30k and well over $100k. During the fat years I never ramped up my spending.

Later I more consistently made six figures or close to it. Still lived cheaply, in the crappiest apartment I could stand in the city's nicest neighborhood. I think that's my upbringing talking there -- live in a nice area, but do it cheaply. Dad mostly did well and always put is kids first, but there were times of unemployment and uncertainty and I absolutely wanted to be prepared for that in my adult life.

Quit my job a few years ago to move out West. Thought I'd find another job quickly, but that was a few years ago now. Anyway, I'm left living in a cheap place in a very touristy/upper-middle-brow location. Since moving here I've been spending as if I'll never have a real job again. This isn't a problem because (a) I have always been frugal as an adult (b) I have plenty of savings (c) I've never made a habit of comparing myself to other people re lifestyle and (d) I live in what I consider paradise.

When friends and family come out to visit, I think they discover they're the suckers.