I don't know if Air America is struggling or dying or doing fantastic. Depends on who you ask, like everything these days. But I do know that it hasn't been the bang-up success that its initial founders thought it would be.
I think the answer is twofold: one from the negative side, and one from the positive side. They're really just two sides of the same coin.
The positive: I don't think people on the left have to be coddled and reassured of their opinions every moment of every day, like people on the right. Righties seem to need constant assurance that yes, they are of course right about everything, and damn those traitorous bastards who are cheeky enough to think otherwise. On the left, largely, I think people have come to their positions over time, through actually thinking about them. Right-wing ideology, to me, seems to be more the product of indoctrination and imposition. That's not to say that some on the left can't be just as rigid and doctrinaire as any Michelle Malkin or Dean Esmay. But overall, I think the idea holds.
The negative: People on the left are so beaten down by the dominant right-wing ideology in this country that even they flinch when confronted with people and ideas that the right finds abhorrent. It's practically stylish in my Commie bubble called Madison to be openly scornful of Michael Moore, for example, even though he's one of the few pop culture figures who have forcefully rebelled against the horrors of the neocon worldview. Lefties can be so conciliatory that they won't support people on their own side if they are too "strident." Let's just get along, be nice and smile, and maybe everyone will hold hands and buy each other a Coke.
To which I say: HELL NO. That time has passed. Fight back. Get in their face. Stand up for what you believe in, goddamn it. Get a bloody nose, and give two back. We didn't start this fight, but we better damn well win it.