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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When I was 20 I thought I was 30 - but I was so far from it. When you're young you want everything to happen now. As you mature you can look back and see all the great things you achieved with time and patience.