I thought about what books I might recommend, and I realize that I have stopped reading books on information technology. Unless you count Cowen's Age of the Infovore, I may not have read any in this century. I agree that Clay Shirky and David Weinberger are interesting, but I pick up their thoughts from the web.
Last century, I read Microcosm by George Gilder. I imagine it will seem quite dated by now, but it really got me to think in terms of a less material economy, and thus represents an antecedent to From Poverty to Prosperity. I also read Information Rules by Hal Varian and Carl Shapiro, and I continue to recommend it. One of my mantras, "price discrimination explains everything," is in some ways a distillation of that book.
Last century, I wrote essays about information and information technology. Here is a summary of what I was thinking about 12 years ago.