Brutal honesty: You have around a zero percent chance of winning solely based on technical merit. Don't get me wrong - you're going to need to get technical m

Brutal honesty: You have around a zero percent chance of winning solely based on technical merit. Don't get me wrong - you're going to need to get technical merit down, you're going to need to offer some great functionality on the technical side. But if you really want to take Craigslist down, you're going to need to take over ONE MARKET effectively and branch out from there. You're going to need to pick one city and walk all around it getting people to use your service, putting up flyers, doing a radio interview, trying to get the mayor of the city onboard, convincing college kids to swap their stuff on there or to meet for board games... you'll have to seed that one city with your own offers, meetup groups, get your friends to post their resumes or job offers on there, etc, etc, etc. This almost certainly can't be done from behind a keyboard. Craigslist isn't winning by its technology - the technology stays out of Craigslist's way while the site wins by community and network effects. You need that. You can't get there via technology, you need to take over one city Craigslist is underserving, then repeat the process a few times until you've got some solid beachheads in place.