I love Chuck's piece, not least because I know this guy and have met his equivalent too many times: narcissistic hipster, flake, self-centered, deluded in the way only the rich can afford to be deluded.
These types may be smart and personable as necessary, but, once burned by their kind (well, maybe thrice burned) you no longer give a damn how much money, brains, or ideas they have. Just not worth the association and the disappointment.