[Hogg]

The Dating Ring (YC in 2014) tried to do that. It didn't quite work out, at least not how they hoped. The second season of Startup Podcast was all about them.

I heartily recommend that podcast. Even if you're not all about startups, I think it's fascinating that they give you a first-hand look into the subjects' attempts to start their company, with recordings and interviews about things as they happen, rather than in retrospect.