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He's a YC guy who made a lot of money in tech and this is a YC website full of people wishing they made a lot of money in tech.

I think you will get downvoted soon (and I for mentioning this) but this is the simplest and most logical explanation on this thread by far.

It is a bit of a cultish environment no doubt. But there are a lot of very very nice people here too.

I would not say nice. Smart, and sometimes cordial, is how I would describe people here.