What impresses me is that you described a good ability to deal with failure, and called it "less able to deal with failure". Because if you can ignore setbacks and achieve what you want, such that it's a "real advantage" where "the rich stay rich", that's a good quality to have.

Imagine if you said that at a job interview. "What's your greatest weakness?" "I think I can achieve great things (or make money, or whatever) and I don't let failure stop me." That's not a weakness.