I’m starting up an online paid classifieds advertising website and am looking for some marketing and advertising ideas that are outside the box.
Believe it or not Craigslist doesn’t cover our area, we only have one newspaper which has a monopoly on advertising to a county of 130,000 souls.

Currently the county residents are being squeezed by the local paper, I think I can do better and have already received commitments from local businesses committing to banner advertise on the homepage, so we are beyond break-even before we ever launch.

My real question is as to how to think guerilla in launching my attack on this newspaper that so many residents and business owners have already voiced their disdain for?

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Let’s set aside the issue that Craigslist can quickly take over your market from you (and in fact, if your goal is to fight the local newspaper, this might be the easiest path — contacting Craiglist) as well as having the newspaper launch an online component to their printed advertising.

You’re asking how to advertise your site when the main form of advertising is your competition. I would suggest starting with the early adopters of online searching. Focus on the under-30 crowd (whether they be at high school, college, nightclubs, bars, music stores, book stores, video rentals, and movie theatres) first. Provide not just advertising, but weekly summaries of “what’s happening” (with the ability for them to post free upcoming community events). That will help start the “buzz”.