National efforts at hyperlocal media seem to consistently face the same challenge: how to find hyperlocal advertiser willing to pay enough to support the content with a few bucks left over for profit.

Unfortunately, this has been a challenge for a number of reasons.

How did we get here? I'm pretty sure the evolution of local media went something like this:

First the Earth cooled. And then the dinosaurs came. A few years later, a guy named Robert (disputed) started chiseling out a news tablet. It turns out that some of the local traders (let's call them all Hank) wanted publicity alongside the news, so Robert started taking ads.

The traders who took ads found that they paid off since Robert was distributing his news-tablets to a hyperlocal community. Robert's news tablets were published so regularly to such a predictable audience that they often became the advertising venue of choice for local traders (and service folks like wagon towers). Robert's readers found the ads valuable as well, since it made it easy for them to find someone local to call them their roof leaked.

Fast forward a disputable number of years: A guy named Al (disputed) invented the Internet, and he guys like Robert - why by now had switched to driving trucks full of paper around their towns rather than hauling tablets - had the option of publishing their news on this Internet thing.

It turns out that it wasn't particularly difficult for guys like Robert to move their media to the part of the Internet called the Web since they were already using computers to create the content.

UNFORTUNATELY, local traders like Hank (and folks like roofers, real estate agents, and restaurant owners) were a bit slower to make the move to the Web. They didn't use computers in their day to day work and didn't have web sites. If they did have websites, they weren't proud enough of their sites to justify spending money driving traffic to them.

That's where things broke down. Hank wasn't in a position to spend similar dollars on online advertising as he'd previously been willing to spend on paper or tablet forms. Robert's distribution costs are now lower, but he still needs a lot of ad dollars to cover the costs of his staff.

If you were advising Robert, what would you tell him to do? How does Robert create an online media site that deserves a similar level of advertising investment from Hank as Hank's used to paying? How does Robert recreate the value his offline newspapers online, both from an advertiser and consumer roll. Robert knows his readers find the ads valuable in the print edition, but hasn't figured out the formula for recreating it on this Internet thing.