As a young military pilot, I ofter heard the sniping comments about rich guys flying planes that exceeded their skill level. Of course, I couldn't afford much but a flying club plane while on active duty.
Over the years, I built a business and have been able to quench my flying addiction by owning my own plane.
A young CFI made a comment when I was in an FBO about rich guys flying turbines and didn't realize I had a KA on the ramp. So, I asked him how much he thought one of those cost. He was way off. I asked him if he wanted to fly one, and of course he did. I asked if he couldn't afford one, how he expected to have someone hire him if they or their corporation weren't well off (in his opinion). He didn't seem to have an answer. Nothing like burning bridges. I do fly my own plane, but I know I'm not a full time pilot and don't want to be. I really train to be good and don't push the limits.
Early in life my challenge was to build skills and qualifications along with building a business. Hopefully, along with doing that I developed enough wisdom and judgement to use those skills now when I can afford to fly something nicer. Be careful with broad generalized statements; one may come back to bite you <g>
Best,
Dave