There seems to be a place here for the 'fan' perspective in discovering what works and what doesnt. I have a story of something that emphatically worked from my perspective, and I think from the perspective of its creators.
The Bugle is a weekly podcast made by John Olliver and Andy Zaltzman. It is a political comedy program in which, "They have left no political hot potato unbuttered, and have presided over, and/or caused, and/or commented on (delete according to preference) the downfall of several of the world’s least desirable despots and dinner companions.."
The Bugle began with two major advantages, which it is worth acknowledging: John Oliver's spot on the Daily Show cast gives him high name recognition, and some people must find The Bugle though that. Second, the podcast was sponsored by The Times of London for four years during which it acquired an audience. But the success story is that after being dropped by the Times, Oliver and Zaltzman managed to get funded purely on their fans' goodwill. I'm not going to minimize their advantages, but I think there are specific reasons they succeeded that go beyond those advantages.
Connect with Fans:
The Bugle is a fan of its fans. John and Andy give constant shout-outs to 'Buglers' who make them proud with exuberant acts of nonsense, provocation, and the subtle art of making puns in inappropriate situations. Most episodes include a "Your Emails" section during which the hosts read listener emails and/or ridicule the senders. They treat their audience like the only other interesting kid sitting nearby in class--the one you have to simultaneously impress and outdo. Every artist should feel this way about their fans: you have been lucky enough to find people who love to see you do the thing you love to do. If that's not enough for you, learn to act like it is--it makes a difference.
Reason to Buy
Some time before there was any hint the Bugle would be cancelled, Zaltzman started maintaining a Twitter feed (@hellobuglers) where he would post and interact with fans (If you're on this site I expect this is 101 stuff). When at the end of 2011 they heard they were being cancelled, this channel already had a significant number of followers. That was important, as even at this stage, the Bugle had only a small web page at the Times Online, and a Times email address. Effectively zero resources had been spent on a website that could provide interaction until that point, much less any strategy for monetization. But Buglers had already been turned into a community--there were lots of us out there, and we identified with each other. The hosts sometimes received gifts/pranks from Buglers irl, a sign that people wanted to contribute, to feel like part of the show.
Finally, when word of the cancellation came, they communicated well. On the last podcasts with the Times, they said they were looking at options to keep going, and asked for offers of support. They kept the mood light, but they explained what their costs were: the show needed to use two studios, as John and Andy live on different continents, and they needed to pay their engineer, Chris (who himself appears sometimes in the show). And they were clear that they wanted to be paid as well, without making it sound like an ultimatum. Their last full podcast for The Times should be required listening for everyone in an advertising or PR course: it doesn't feel like a pitch at all. But when their contract ran out, they built a website with a voluntary subscription portal, made an episode and put it on SoundCloud, and explained that they were going to be listener supported. It made them nervous, and that wasn't really disguised, but they were taking a chance.
At the head of the second independent episode, they said they had raised enough 'to keep us going for a few months at least.' I am not sure how this rates in dollar terms, but I will say two things: 1) I think they did pretty well, and I think that if they make it known in a few months that cash is getting low, they'll do pretty well again; and 2) If the listener-supported thing doesn't end up working out, I cannot imagine a better bargaining chip to have on the table when setting ad prices than, "...and XXX of these people have already been motivated to take out their credit cards by this show alone, which they could get for free."
Like I said, they started with advantages. Maybe in a lot of successes, that kind of luck plays a role. They seized it and made it work for them. There are a lot of supporting parts on high-profile shows who never manage to get good projects of their own. There are a lot of talking heads in newspapers these days. But they took that into the new economy and parlayed it into a business model. As John Oliver would say, that's not nothing.