Things you should know about Damon: He works at Google (as their "in house philosopher," whatever that means??). He's a Columbia grad. He may or may not be at least part robot. He's disgustingly smart. Oh, and he became a millionaire when he was like 24 or something for selling some startup he made. He doesn't talk about that stuff in class, but it definitely clarifies some of his weird professorial idiosyncrasies. Damon knows the material well and expects you to, too. Being able to participate in discussion is a big deal. Damon isn't the kind of professor who will fill awkward silences with rambling lecture; he sits, he waits, and if no one says anything, he'll give a little disappointed sigh and ask another question.
He expects you to do the reading, but he's not evil. He went here, too, and he's pretty familiar with the Columbia workload. If you can read enough to participate in lecture and know at least one idea from each text backwards and forwards, you're in good shape. His midterms are easy, he grades papers fairly (especially if you go in to talk to him about your ideas), and he's a generally nice guy.
Not very engaging as a lecturer, though (he puts weight on you as often as he can), so make sure you have people in the class that do the reading. 2 hours of crickets does not a CC class make.