Not quite the same thing, but it is sort of heartening that Marco Arment -- of Tumblr, Instapaper, and now Overcast fame -- was able to build out his own non-scummy ad buying platform for his Overcast app. It seems to be doing quite well.
I know one person who ran a listing so far and they are very happy. It's about putting the right sort of "ad" in the right place. Advertising podcasts in an ad where people are listening to podcasts is a no-brainer and engagement should be high.
Advertising arbitrary services, even if they're good, on arbitrary blogs seems trickier to price and sell. But with the quality of the sites in the network, I'm sure they could all individually find the right, complementary type of advertising to continue to fund them.
What makes podcast ads so much better? I'm not referring to overcast ads.
I think the only thing I've ever bought based on a podcast ad is BackBlaze, but I do find podcast ads for the podcasts I listen to much better, more relevant, etc., I've just never been in the market for most of what they are selling.
Yev from Backblaze here -> thanks for purchasing! I think part of that is when I find places to run a Backblaze ad, I try to find a show-host who is willing to do the read themselves, try the product, and maybe share a personal story instead of just reading blanket copy. That doesn't happen all the time, but when it does it comes off better. Backblaze is a tough thing to market because a lot of folks view backup as a horrendous time-sink - so if the host can drive home the ease-of-use we see folks more inclined to giving our trial a spin!
The way most of them are delivered makes them more like native advertising. As long as a percentage of listeners engage, it has value, and that percentage is higher than engagement via sidebar ads on the Web it seems.
There's also a certain remaining level of novelity in podcast advertising that helps it command a premium, although I suspect this is beginning to diminish.
https://overcast.fm/account/buy_ad