Startups Rival Craigslist for Online Classifieds Market Share
betakit.com
betakit.com
It's much easier to market to a small geographic area first. One great tip I heard in a Mixergy podcast came from the founder of GrubWithUs. To get started, they printed 10,000 flyers and went around stuffing them into the free daily papers in their hometown.
Once you get going in a small area, then you can expand out. This is the only way to win against craigslist.
(for the record, I think that the way Craigslist runs things is both admirable and idiosyncratic: it works very well for them, it wouldn't necessarily work well for others)
It also realizes that sustained profitability is achieved by leaving so much money on the table that any possible competitor is going to have a really hard time covering expenses.
Generating positive social goodwill isn't a bad side-effect either.