It shouldn't be a surprise that Air America failed--because it was a poorly constructed, poorly run and in many ways poorly staffed outfit from the get-go. They had a handful of genuine stars pass through their doors at various times, like Randi Rhodes (who they treated badly), Al Franken (for whom it was a way station toward his real love, politics), Rachel Maddow (who is best on the tube) and Lionel (who got there too late to make a difference). But they had amateurs running the front office, the sales and marketing effort, and even the technical operation of the network. And they totally whiffed when they had the opportunity to reinforce their talent roster with people like Ed Schultz, Stephanie Miller, Jay Diamond, Jay Marvin or Joe Madison, all of whom would have fit well and added credibility and luster to the lineup. The people who ran it, did so in a manner reminiscent of college radio--and not in a good way.
It's more surprising that Air America survived for a half dozen years, while most inept organizations fail far sooner. That speaks, not to the failure of progressive radio, but to the fact that a demand for it exists which was strong enough to keep an incompetent organization alive far beyond the time when most such organizations normally sink to the bottom. A well run, professional outfit with depth of talent top to bottom still has a tremendous opportunity to capture a large and loyal audience of people tired of more typical commercial talk radio. Air America proved that much, despite its amateurish incompetence. It'll be interesting to see if anyone with a real understanding of the business of radio is sharp enough and gutsy enough to give it a try.