http://letsfreckle.com is totally livable for two people right now (about $150k/yr and growing), but since I want to be rich, we're rolling all that money back into expanding it.
You have a very good memory! Yeah, I won RailsDay (the first contest, a 24-hour one, supplanted later by RailsRumble) with a wedding planning app called Freckle. But that never got anywhere as a product. I just reused the name because I like it.