Air America's biggest problem was that its passion far exceeded its professionalism, both on the air and behind the scenes.
A few people who were genuinely talented star broadcasters were on their schedule at some point in their nearly six year existence--Al Franken, Randi Rhodes, Lionel and Rachel Maddow come to mind. But Rhodes got fired due to an overblown incident in a San Francisco personal appearance, soon to find her way to another syndicator and a brighter future. Al Franken went to the United States Senate. Lionel came on board too late to pull a substantial number of clearances from stations to pull a struggling network out of the mud. And Rachel Maddow, who hung in there the longest, clearly outclassed everyone else remaining on the roster and is now a star of cable TV. I don't mean to disparage the others I didn't mention; some of them in time might have grown into compelling radio personalities. But some were hopeless and so many of them, even those who in time might have developed into outstanding hosts, came to the table with little or no experience in what makes a good talk show work. The network failed, when it had the chance, to recruit other experienced, talented broadcasters who would have fit in well and added to the network's strengths, like Ed Schultz, Jay Diamond, Joe Madison, Jay Marvin or Stephanie Miller. Add to that some senior administrative, marketing, programming and technical people who were long on passion but very short on practical experience, and you had an operation which resembled a college radio station (and not in a good way).
Hey, I don't claim to know everything about it myself, who does? I'm still learning new things about what works and what doesn't, like everyone in this business. But at least those of use who've been doing it a while have a clue as to what needs to be done to keep things going and keep their stations in the game. And we sharpen our skills as we go along. Air America lacked that growth on just about every level you can imagine, and never seemed to get its act fully together.
In the end, it shouldn't be a surprise that it failed--because it's more surprising that it survived for a half dozen years, while most similarly jerry-built broadcast organizations usually 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 a VERY poorly run organization afloat far beyond the time when most such organizations normally sink to the bottom. A well run, professional organization with depth of talent top to bottom still has a tremendous opportunity to capture a large and loyal audience of people tired of the same old, same old from 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.