I think you are making some pretty broad assumptions about a whole bunch of things.
First, this very article is about an immigrant, with no status, money or connections, creating opportunity for himself.
Obviously, I am gonna be somewhat biased by my own upbringing, so I can't be truly objective (other than knowing that I grew up in a vastly different upbringing that the folks you describe, yet still feel there are some rules that should be broken and others that shouldn't be crossed.
My only two points I would make are:
1. YC Funds a pretty diverse crowd from all over the world if I understand correctly (I have no direct knowledge.)
2. Founding a successful startup isn't for everyone, and maybe it favors some over others due to life circumstances, but that doesn't change the reality that to innovate and succeed, you might need that "naughty" mentality, regardless of whether it came from a place of privilege or not.
Finally, In my experience, persistence is by far a more important trait for success than almost anything else, and the most driven, focused, persistent people are often the ones that fought against all odds to break free from their underprivileged circumstances, much like the immigrant you described. I am not sure they feel a need to play by arbitrary rules or not, but even if they do, they often rise above through sheer force of will...and often that persistence, and will power brings them to do things that open doors by ignoring propriety and breaking down barriers and limitations that live in their head more than anywhere else.
I might be biased about all sorts of privilege and might be blind to the class bias you refer to, I do not know...but my gut and experience tell me that individuals and their personal decisions matter much more than their class and circumstances. (Not discounting those other factors, just discounting the role they actually play in reality relative their own choices and of course colored by my own bias.)