Philip Greenspun tells the story (audo version) about Ars Digita, what went wrong and other things. It’is still worth reading.
It reminds me of all the fun we had at Nua. Learned lots there.
He also makes some excellent points about the problems of open source. The problem is that you have to be extremely efficient at delivering projects and modifications to the software you developed. These modifications and project work are the only revenue stream you have (as opposed to closed-source, where you make money from licenses).
Greenspun’s book on web publishing is still well worth a look.