What's interesting to me is that no one seemed to think to formulate a profitable business model before sallying forth. There are plenty of smart Democrats around who could have devised one, particularly among the Hollywood types (they know how to make entertainment quite profitable after all), so why didn't they? I smell an upcoming book about what really went down in all this. Here's hoping P. J. O'Roarke is the one who writes it.
Because this was never seen as a business. It was designed to be nothing more than a 24x7 political advertisement, primarily saying "Bush is bad!"
On the other hand, it's also possible that the people in charge were so incredibly myopic that they never realized that "conservative talk radio" is popular because people need an outlet that doesn't exist elsewhere. Anyone who's a "true believer" simply can't believe that someone else would believe the other side's story. There had to be SOMETHING that the Rush Limbaughs of the world were doing to get the audience. It certainly couldn't be the content of the shows...
Mark