Having style is knowing when confetti is "Voice" versus "Clutter."
Great small companies have more room to have Voice. It is very hard for large companies to have it. Or the larger they get, the more they worry about offending someone. Tumbler can have Voice. So can Tech Crunch. Hard for Wal-mart to have Voice.
That said--and without having much other context for Fred Wilson's idea of "voice"--having fun with a company's homepage may work for some organizations and not for others.
(And specifically regarding milestones, Facebook has deliberately taken a much humbler public approach. Let's see what happens when they hit a billion users.)
Facebook used to have a distinctively irreverent voice ("I don't even know what a quail looks like"). It's slowly been whittled away as they've gotten huge.
Google, on the other hand, maintains their voice but keeps it out of the main flow - think doodles or bidding Pi billion dollars. So it's not just a function of size.
"Personality" would probably be a more obvious word for it (although I guess "voice" is specifically personality expressed through product rather than through company actions).
It's all or nothing though, either you have these sites which are free to upload and try and clean up after later on or you have everything has to be moderated which is completely unsustainable.
sycophant seems to be the norm for the comments at avc.com On this particular post I wouldn't call them particularly disgusting though. I've seen much worse. And in general any disagreement with his thoughts are very nicely said. You rarely see anything snarky or mean spirited.
People are hoping to get some of the pixie dust. I don't think this is really different than the halo that surrounds any successful person.
In the movie "Born Rich" by Jamie Johnson, Ivana Trump was interviewed (it took place 2003). She was surprised by all the people that wanted to be friends with her and treated her nicely. She said something like "I mean I don't have any money my parents do". That's the halo.
... of the "real id" effect, under democratic conditions. The people who earn their living elsewhere don't care to risk it telling the truth, so you get the sycophants showing up trying to lick brownie points ...
Which just goes to show the Vivek Gundrota (real name, not the spurious Vic he sports) Google+ policy is dumb. And why the whole 'social' Google should be taken out and shot.