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I'd like to hear more about this. I've been thinking of getting more into photography myself. It seems like wedding photography is a bad idea as it's way overdone. I was thinking architecture or portrait photography. What did you all end up doing?
I think an avatar photo business would be a good idea. Think of all the twitter users with resized photos of themselves that are unflattering, cryptic, or just plain bad.
The trick with headshots is enough finding people (close to you) willing to pay enough money to make it worthwhile. That usually means actors, authors, or executives.. but I'm sure increasingly wide-eyed young startup kids and software developers make the Bay Area an interesting target.