Found this (h/t BusinessPundit.com) blog entry that tells of the trials and tribulation of a startup — mycarpoolstation.com — that is struggling. Lets learn something from their difficulties. From the entry,
We did not find the perfect product/market fit.
My original vision, circa 2005, was “to supply web-based, community-run carpool stations to schools, workplaces, and regions in the U.S. and Canada” (i.e. to build a Facebook clone but for carpooling). We would make money off ads exclusively. By the time we finished building our Alpha in 2007, we ran out of resources and realized that we needed to build something different to execute my 2005 vision in 2007/2008: we needed to build a Facebook app, an OpenSocial app, a stand-alone website, and offer enterprise-branded carpool stations with an API. Of course, if you’re bootstrapping you’re going to have to build traction and release these one at a time. The business model would probably change as well. It would be ad-based for app users and membership-based (with no ads) for website users and enterprise users. There’s also the possibility of a token-based economy.