Scott Weiss

At the core, coaching authenticity is complicated - some might say impossible. Telling someone to be authentic sounds pretty low calorie, especially to a founder plowing through a list of product and operational goals. But it's important.

One of the rookie mistakes first-time entrepreneurs often make is to be too guarded about their idea - in fact, many will actually spend their first $25,000 on patent lawyers without ever fully vetting their product.

Being a good Hans Haacke student, part of his influence on me is that there's no difference between a gallery show and a film - or even an ad and a T-shirt-in terms of cultural legitimacy. They're just different contexts in which to have some sort of communication.

Unlike the LeBrons and A-Rods of the world, anointed as special from pre-K, Matt Leinart exudes an approachability rarely seen in superstars. It's why kids on the autograph line chat him up like a buddy with whom they could stay up late playing Xbox.