> The solution will probably entail geolocation, semi-anonymity, and perhaps ephemeral (that is, non-persistent) IRC-like chatrooms.
Checkout chatimity.com (my startup). This part of your comment is spot on for us :) It is a geolocation based, pseudonymous IRC-style place with some behavioral tracking and modulation to keep the place clean and civilized.
One way to deal with creepiness of friend requests is to not have them "mutual". Friendship in real life is one-sided relation and so could be on a meet-new-people platform.
This is one of the insights that we have used at Chatimity (www.chatimity.com) - for building a place for making new friends online. It is like old style chat rooms but much more civilized due to a good amount of behind the scenes measures being put in place. We have had fair bit of adoption and continue to flesh this out more.
You could use ticker names and quotes from one of the real stock exchanges to start with. This could act as base prices with some changes due to buying/selling in your engine. Till you get lots of users.
Hardest factor that keeps me away from the "zone" is: the task-at-hand being uninteresting and grungy, which is typically the case at regular jobs. Any tips on how folks overcome this factor? Other than to go built my own startup.
With anything uninteresting, try and come up with a solution that challenges yourself to think. Say, instead of using that plugin you frequently rely on, come up with a solution of your own (of course, keeping time constraints in mind.)
Checkout chatimity.com (my startup). This part of your comment is spot on for us :) It is a geolocation based, pseudonymous IRC-style place with some behavioral tracking and modulation to keep the place clean and civilized.