What should I ask him?
Carr's newest book is The Big Switch, which applies an overarching metaphor to the Web-ification and the broadband-ization of today's world--he finds it analogous to the development of the electrical grid. (His book is, obviously, much more nuanced and textured than that grievous oversimplification.)
On his excellent blog Rough Type, he's written (along with many other things) his doubts about the Web 2.0 economy and the wares it produces.
I'm looking forward to this conversation immensely. But, as always, I'm curious to hear what you think would be an interesting question or two to ask.
(The obligatory disclosure: My wife, Laurel Touby, founded Mediabistro.)