He was surprised when I said that it was well within his ability to do this already. Not in a "woohoo I put up my own website with my own shows" kind of way, but in a "I have become my own virtual CDN via EC2 et al" kind of way. He argued that would simply make Amazon and the infrastructure providers into the new middlemen. Perhaps, though that might be like saying that my computer use is being held hostage by the electrical company. In theory it is, but in practice it does not feel like the very exploitive sort of middle management that exists in the entertainment industry.
I've done some work for this industry and the key point you have to understand is that, whereas "Can we accomplish this?" is a matter of technological feasibility to us hackers, it means something entirely different to entertainment industry folks. To them, it is more of a legal matter. The whole industry is mired in a complex web of contracts governing every detailed aspect of intellectual property. So, when we scoff at how long it took the networks to get something like Hulu up on the Internet, understand it was a bunch of lawyers holding up the process. Then, when you get around some of the service's limitations (e.g., geoblocking) understand that too, was a dumb legal requirement. Everyone involved knows these restrictions are circumventable but, they must be in place for the existing contracts not to have to be re-negotiated.
Talk to anyone that's worked on the iTunes infrastructure. From what I gather, at least initially, getting an album onto the iTMS involved dozens of contracts. It made getting an iPhone application onto the App Store a cakewalk in comparison.
Where a startup could provide tremendous value, it would be in overcoming the legal hurdles to distributing content on the Internet. Spend the money on the lawyers to setup all the contracts that you need, so you can get unsigned artists onto your content distribution network, but more-or-less play by the rules of the current industry. These people are afraid of change, so you don't want to come out of left field in the way you operate. Then, when you become the new boss of the industry, tear down the stupid legal constraints that stifle creativity and innovation, and makes the Internet pretend to be something it is not.
The networks are vulnerable. Writers, actors, and other workers hate working for them because they take huge cuts of revenue and then play accounting games to take an even larger portion. There's a reason the unions there are so strong. They're united in their hatred of the middlemen. On the other side of the coin, us consumers hate the networks too. Most of us are tired of their antics.
So, any startup willing to take on this challenge would have a friendly set of content suppliers, and a captive audience. Just get yourself the best lawyers you can probably find, because you will need them ;)