I love this video. I love all of Casey's videos, please check them out.
I'm intrigued by Chatroulette, not by what it is now, but by what it could be. What if there were some structure to the site? I love the face-to-face aspect and its randomness. I would love there to be a system of categories so that you could filter the kind of people you might want to have a conversation with. For lack of a better term, I see this as a way to host a digital office hour. I think the categories could be simple like Craigslist. Build in some networks and this service could actually be useful.
What if there was a medical section and doctors volunteered their time to give medical advice? Want a second opinion? Next. What if your professor hosted office hours with this kind of service and you didn't have to wait hours outside of their door to ask your question and show your work? What if a politician hosted conversations with constituents? Or what if there was an option to publicly host your conversation?
I'd like to see topic categories as well as geographical categories. Maybe you want to talk with people in other parts of the world, or maybe you're best audience is within your own town? Maybe this could be a way to share our conversations with one another?
There is a lot of value in face-to-face interaction and I think this idea could go somewhere. Right now it's just a bit disturbing. There's not a lot happening there and it's not constructive.