I think being a wealthy member of the establishment is the antithesis of cool. Being a countercultural revolutionary is cool. So to the extent that you've made a billion dollars you've probably become uncool.
My interactions with Sorkin were agonisingly weird. He is by far the weirdest...
I never had a cool older brother or sister to turn me on to cool music. I had...
I failed to make the chess team because of my height.