I used to do a lot with small regional papers (I worked for Freedom Communications). They are a tough sell. Super slim margins, very reliant on and subject to t

I used to do a lot with small regional papers (I worked for Freedom Communications). They are a tough sell. Super slim margins, very reliant on and subject to the whims of the local economy and were completely disrupted by national (or multinational) online players. The race to the bottom in local advertising markets in terms of low value, high return and high volume plays through broadsheet classifieds, craigslist, daily deals, etc has put the ethos of what a "small town" paper was out to pasture. It used to be communities were defined by their media, and these newspapers existed to help define them through editorial voice and amplify the community through advertising. That's a tough game now. Consolidation killed the independence (Freedom for instance bought up all the local Orange County papers), nationalization and the ability to localize the global killed classifieds. It is however a field ripe for some disruption, as the need for local media and localized sales-forces is there, but the ability to address the need with a sustainable business is tough.