Zeek’s Michaelson reflects personally and politically:

That’s the trick, of course; as soon as something becomes big enough for the mainstream — even the alternative mainstream — it’s lost its edge. This is what’s pathetic about the Jewish institutional world’s belated attempt to jump on the cool-Jew bandwagon: all that effort, and the ive-minutes-behind-the-times style, just makes them look even lamer. What’s more, cool has always had a rebellious, undermining quality. Take away the edge and what’s left is MC Hammer: sanitized hip-hop for white suburban kids. Likewise the attempt to co-opt superficial design elements of “Jewish cool” without its underlying critique of established Jewish categories, assumptions, and sacred cows. Again, it’ll fool some people —
but it can’t be actually cool.

(see also Sh’ma‘s previous article on Marketing Cool)
Jewschool rhymes with cool…does that help? Or does having school in our name just make us nerdy? Oh wait — nerdy Jewish is cool, right?