More valuable than the long tail is that he probably has an email list of ~20,000 people -- and more by the hour -- who have demonstrated interest in paying money for Louis C.K. comedy specials. I trust I don't need to tell you what to do with that if you're the exclusive producer of Louis C.K. comedy specials.
When you go to the purchase screen you can choose between "contact me," and "don't contact me." To Louis' credit the default is "don't contact me," but I as a fan actually opted in to receive future notifications. I fully expect to be notified next time this opportunity arises (and I am probably not alone).
I opted in as well. I was sort of disappointed that the results of the "opt-out sub-experiment" weren't discussed in this statement. He's mentioned it in interviews - on NPR and repeatedly on reddit, at least - that he's got huge feedback on that little decision. It's also something that people, present company included, love to talk about. It would be interesting to see how many people decided to opt-in because he defaulted to opt-out.
I'm curious where you're getting the 20k figure from. He mentions only that he's sold over 110k copies, but not what percentage of people opted in to the mail list.
Its a guesstimate based on what clients of mine or I get for opt-in in similar situations, with a discount based on his customer population disproportionately being Redditors or demographically similar to them. I figured "Meh, 20% sounds about right."