If that's true, please count me as pseudo intellectual also, because pg is one of the smartest people I've met and I continue to be in awe of how his mind works. I know it's silly to post such a thing, as the bias/conflict of interest is obvious and it will inevitably come across wrong—but I've thought and said this long before I met pg or had any connection to YC, so if there's a causal arrow it goes the other way.
People have had this kind of reaction to his writing for 20 years now and I've been puzzling about why for a long time, because even though I often don't agree with him (sometimes I disagree, more often I have no opinion), I wish I could write like him and know of few other writers who come close.
My current take: I think pg's unusual quality is that he thinks for himself. It used to be a truism that one should "think for oneself" (and even "question authority"!)—not so much anymore—but although we all tell ourselves we do that, mostly we don't. We mostly repeat things we've cobbled from other sources, usually sources tagged as authorities in our minds (and usually also in the culture at large). If you cobble from enough sources and have a bit of taste, that's the sweet spot for getting a good reception. You'll come across as clever and creative, but not weird, because you haven't left the tribe.
When encountering someone who actually does think for himself, the reaction is often a WTF. How dare he do that! Where are the citations?! Thinking-for-self stands out, not in a good way—and in pg's case the ruthless editing makes it stand out starkly. It's off-putting. The reaction isn't "hey, what would it be like if I thought for myself?" It's "hey, you can't do that."
The "rich and famous" aspect is a red herring because pg was this way long before he got rich and famous (except Lisp-famous), and it was by this quality that he got rich... that plus a lot of energy. But the rich-and-famous aspect intensifies the WTF reaction. It's no longer just "how dare you", it's "how dare that rich motherfucker" - which again, gets the causality the wrong way.
I know this sounds harsh about the cobbler type but I know these things by tracking them in myself—I'm no different. The funny thing is that one can notice such things and still feel perfectly sure about "thinking for yourself" or whatever else it is.