It's pretty obvious web radio died because of usurious royalty fees [1] compared to terrestrial broadcast.
[1] http://usatoday30.usatoday.com/tech/news/techpolicy/2002-07-...
Radio still has to be a wildly popular format, even though I don't listen to it anymore. Otherwise, Sirius/XM wouldn't still be in business, despite having a limited selection of music and terrible sound quality. All those subscribers can't just be there for Howard Stern.
Also, digital music has become extremely popular, just not online radio. That could be an issue of quality (low) compared to selection (high) or just that a lot of people who utilize connected devices for music prefer listening to their music on iTunes, Spotify, Pandora, etc.
By investing in both sides of the fence, on-demand and curated, they can capture both audiences. And by hiring people like Zane Lowe, they are giving people additional reasons to go listen to radio vs. on-demand.
Exactly. Music is one of the most hype-sensitive industries. It's good that Apple is in the space, but they should be very careful about trying to be 'cool' about it. When they had U2 play some hits, that was innocuous enough. When they released a 'few U2 album' that was actually offensive to people (for a variety of reasons). Then, when Bono came on-stage and high-fived Cook, well, let's forget that moment. Surely their PR 'feelers' are aware of this and should've warned them that letting Drake ramble on stage would not be a great idea...
"Web Radio Not Making Waves - An unfulfilled Internet vision: thousands of low-cost stations to challenge the status quo."
as titled by LA Times in December 13, 2001, see the article:
https://web.archive.org/web/20011216053056/http://www.latime...
(Many web radio stations are still alive, but the hype is gone)