Social sites really aren't easy to monetize without pissing off your users. MySpace imploded, Twitter still isn't profitable, Google backed off'ish from Plus,

Social sites really aren't easy to monetize without pissing off your users. MySpace imploded, Twitter still isn't profitable, Google backed off'ish from Plus, etc... I think Facebook is one of the few that seemed to successfully monetize a free social site. I think the issue is that Pao (et al.) genuinely don't understand their community. That's the major source of the friction. Consequently, they can't figure out a realistic plan to build a healthy business around it. They seem to manage to piss a large percentage of their community off with every minor change they try to make. It's a bit sad because it's a huge community. Possibly Aether (http://getaether.net/ http://getaether.net/) might be something like what you have in mind.