Radiohead tried a similar experiment to Louis C.K.'s back in 2007 with their album In Rainbows. But after 3 months they decided that the online sales weren't working out and that they should pursue the more traditional avenue of selling CD's out of retail stores. Two similar stories with vastly different outcomes.

I say that it's similar because both are well established acts in the entertainment industry, releasing their work unencumbered by DRM (or other encryption) via a website. As I see it, the main differences are (in very general terms):

- Radiohead said that fans could pay whatever they wanted for the album, Louis C.K. charged $5 - Radiohead are a band, Louis C.K. is a comedian - Radiohead tried it in 2007, Louis C.K. in 2011

Of these 3, the most significant difference that I see is that Radiohead didn't set any price tag on their work while Louis C.K did. By some estimates more than half of the people who downloaded In Rainbows did so without paying a penny for it. Louis C.K., on the other hand, charged $5 right up front. The price tag was so low that it was a pretty easy decision for most who bought it, but it was there nonetheless.

I think that speaks volumes about setting customer's expectations appropriately, an area in which the software industry traditionally shoots itself in the foot. Ask your customers to pay something. If you have something of value, they will.