It's not just the money. It's finding a web development company, meeting with them multiple times, risking $30k (which is not chump change even to him), and waiting for the site to be developed, giving feedback, etc.
They used PayPal + S3 to do Louis CK's site. This kind of thing isn't very technically challenging anymore with the infrastructure that's available now.
I agree that there's a huge opportunity for digital publishers in this area. I just think it's going to be a market driven by the companies that can take someone from material through polish, production, promotion and then distribution.
Just as today there do exist companies that press CDs and companies that box CDs and companies that ship CDs from one warehouse to many retailers yet the market is truly driven by those who can take an artist from material to digital master. Everyone downstream is commoditized and generally gets or loses contracts based on shmoozing rather than merit.
I'm sure there's money in being the digital equivalent of the plucky independent CD printer/boxer/shipper. But you're going to have a hell of a time getting business from people who don't have a digital master yet (and most won't), regardless of how attractive your rates may be. And in the process of those people getting a digital master - they're likely going to be steered toward the distribution services recommended by those people who helped them create and promote that master.
They used PayPal + S3 to do Louis CK's site. This kind of thing isn't very technically challenging anymore with the infrastructure that's available now.