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.

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One of the amazing things about the Internet is that the content creators are the gatekeepers. We can think of an idea and execute it quickly and we didn't have to pitch the idea to a major network or convince a studio head to sign-off on the concept.