Well if you are disrupting old established markets then they will have already coated themselves with political armor, that the livery business goes back several centuries its not surprising that this is so. That said, it would behoove more companies that are attacking such markets (music distribution, and publishing come to mind) have a person who does exactly this, they look at public policy and the way it is being manipulated by the 'competition' and work to counteract that manipulation. John Gage at Sun had the title Chief Science Officer but his day to day duties involved understanding government processes, political movers and shakers, and how those processes worked for, against, or neutral with respect to Sun's goals. He was instrumental in getting me access to the NSA when we wanted to ship strong encryption in an interpreted language.
I wonder if the necessary consequence of this is to get involved with lobbyists. Not necessarily to lobby, just to pay them for an understanding of how the local politics work.
This would also be a big bonus to YC, if they managed to provide domain knowledge in this respect. Because what the hell are you supposed to do in a situation like that as a fledgling start-up?
Well, when you're doing things that violate the spirit of the law (if not the letter), I think it's probably wise to invest in some lawyers and lobbyists.