More generally I made an effort to leave out things that weren't relevant to the main narrative themes of the book namely that there were two sides to Steve Jobs: the romantic poetic countercultural rebel on one side and the serious businessperson on the other.
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.
People are at their happiest if they are true to themselves. I think that applies to their chosen profession friends and relationships. It goes for your health too. If you are true to yourself it seems to me everything should work out pretty well.