During his career working for Wall Street investment banks, the Yale University Law School graduate had collected Picasso artwork, driven a Rolls Royce and flew his own plane.

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To get an idea of the gulf between the ivory tower and Main Street, take a look at the essay by Yale professor Robert Shiller.

FORBES: Taking the Plunge

He started getting calls from Wall Street firms and media businesses (he won't name names), and also one from a Yale alumnus who told him the school's football team was searching for a new coach.

FORBES: Careers