If they're talking like the person that was described was talking, I absolutely would take away from their success, especially because they've never had to worry about any of the stuff that someone who doesn't come from means has to worry about.
Don't get me wrong; finding success is hard, and whenever someone does find it, it should be celebrated. But those that do find it shouldn't discount the struggles of those who aren't able to try, especially if it takes them several tried to find it themselves.
Why? Because they are an asshole about it? That doesn't reduce their success in any way. If they have offset the losses of their previous endeavors, they have provided a net gain and it's still a success.
Because they're an asshole about it, and because they're ignoring the pure luck advantages they had which made their success possible. And it doesn't matter if they've offset the losses of their previous tries, they still took multiple tries (in and of itself not a problem), which is something most people don't get.
Let me ask a question - what does your attitude benefit you? It seems mostly to make you bitter about things that were never in your control, which seems like an unvarnished negative. Maybe you've found something more helpful.
I don't think many people have an attitude of "we need to recognize built-in advantages, and should call out people who try to play down or hide them" to benefit themselves - it's an attitude and position adopted to try to benefit those without those advantages. E.g. by showing a beneficial side of certain social safety net policies, or the downside of the default position becoming graduating with massive amounts of student debt, etc.
Warren Buffet doesn't discourage and shit on those who haven't been able to do what he has. Again, I would discount the person's success because they're an asshole, and refusing to acknowledge that they were given many privileges and benefits by pure random luck. Buffet routinely acknowledges that he had lots of help getting to where he is today.
Don't get me wrong; finding success is hard, and whenever someone does find it, it should be celebrated. But those that do find it shouldn't discount the struggles of those who aren't able to try, especially if it takes them several tried to find it themselves.