"$1000 to do something awesome": the Toronto Awesome Foundation
awesometo.wordpress.com
awesometo.wordpress.com
You can read about some of the things funded by the Awesome Foundation at http://awesomefoundation.org/blog/ .
(Why did I link to the Toronto one? One reason only: that's the one I happened to come across first. I guess SF or NYC would be of direct interest to more HN readers. The Boston one was first.)