On the spectrum of adherence to an arbitrary standard of Proper Written English (TM), there's counter-signaling, a great region of "You just can't write well", a region where one writes very well with errors, and then things bifurcate at the top where a) you write perfectly like the New York Times and this signals status or b) you use non-standard grammar, and that is OK, because you're a better writer than any English teacher and everyone knows it.
Just a bit of literary criticism here, take it or leave it: when I read the classic articles on your site, with the ransom-note formatting, the presentation often overwhelmed the content. I mean, anyone drawing that much attention to their rejection of social norms must mean that to be the primary purpose of the performance. I often slogged through -- and it was a slog -- to get at the meaty arguments hidden somewhere in the pink/green/etc text.
I'm totally on-board with grammar being essentially arbitrary and fluid (this is a True Statement about material reality), but given that this is true, the Dave-maximizing approach is probably not to say "stufz da grammerz!!1" but rather to write well-enough-to-be-understood and not care about the occasional transgression or three.
(There are other writers who make the stylistic choice to be near-perfect paragons of English grammar -- that totally works, too. It communicates something a wee bit different, for example that one is really going for university professor levels of erudition, but that works for some people. PG's writing style, for example, causes me to pull out a dictionary if I see a spelling mistake because it means there is probably a word I haven't learned yet. On the other hand, I generally tend to aim for about a 98% on the mechanics of standard English, don't sweat the last 2% all that much, and frequently break the rules for comedic/dramatic/etc effect. It's much more noticeable when you aren't breaking the rules all of the time.)
This is entirely compatible with continuing the iconoclastic Dave McClure branding, because that branding is a consequence of thinking fairly radical thoughts and articulating them, rather than being entirely a consequence of the packaging of thoughts that are under the surface exactly the same as every other VC's.