I know this is a message board and we're all committing message board thinking, but snap out of it for just a second.
We're talking about a real person --- a person who by the way is posting on this very thread --- who runs a real business. From what I've seen of that business, it runs, successfully, the way he describes it. I wish we'd stop talking as if Fried was Chairman Mao and we're really debating global communism.
He's a great CEO (at least in the context of 37 Signals), and has a set of values which are internally consistent, and sits on a board of a company which is inconsistent with those values. I'm not sure how to reconcile this with my belief that boardmembers have a responsibility to exert governance and oversight over their companies.
Based on reading his responses elsewhere in the thread (left the board in 2010, was his first board seat, novelty, etc.), it makes more sense. I guess I am overly sensitized to passive board members from watching HP, Yahoo!, eBay, RIMM, etc.