I don't think that's fair. First of all, in some sense Thiel is one of those "weirdos" you mentioned above as a gay man. But that aside, the more modern versions of those enterprises -- google, facebook, uber -- were all funded by that "button-down conservative culture". It is hard, if not impossible, to call the success of those enterprises as anything but cooperation between "the weirdos" and people like Thiel.
And it is of course ridiculous to say that Thiel isn't genuinely a member of the tech community: if partners in ycombinator aren't genuine members of the tech industry, then who is? Just the engineers?