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Success models for city sites have been elusive. But entrepreneurs still believe they can provide a local edge to city sites that can’t be done by portals like Google, Yahoo!, Microsoft, Ask and AOL. And they hope their “not-so-secret sauce” (low salaries, volunteers, hip content, automation, better tools and more compelling salespeople) is better than those that have gone before them.

The two newest candidates to come across my desktop are Pegasus News in Dallas and CitySquares in Boston. Pegasus (named after Mobile Oil’s logo, which has become the de facto logo for Dallas) has been built up from the event site. It is more broadly positioned as an online newspaper with sections called “metro,” “business,” “sports,” “schools,” “living,” “business,” “school,” “arts,” “music,” “movies,” “dining” and “shopping.” It incorporates a lot of press release feeds a la Your Hub and features a steady stream of blog content as well.

For a new site, all that segmentation  not to mention a big push toward personalization via “The Daily You”  usually spells “ghost town.” But Founder Mike Orren, who runs a 10-person team, says “we make sure we have coverage everywhere. It is very easy to find news from a town council or ISD (Independent School District) to fill in where needed.” The site also populates its content with Topix. When there is enough traffic, “we’ll weed out some of the more marginal ones and/or merge them with others,” he says.

In Orren’s view, user-generated content is going to ultimately make or break the site’s usage  and advertising and e-commerce follows. He eventually did well with the music site, which now profiles 1,300 local acts. But he thinks he can do better with a more broadly targeted site. “It took us about three months to start getting over the transom submissions on TexasGigs, but we’re seeing more early engagement here. We already have three good new content partners since launch.”

For sure, I admire the breadth of the Pegasus site. But the question I ask myself is  Iraq coverage aside  is it any kind of substitute for The Dallas Morning News? More important, do I detect a major disconnect between PTA school content and kids exchanging tips on Goth bands? My hunch is they should leverage the music stuff more.

But Orren politely disagrees. “The music focus is just because our archive is stronger there and will balance out over time. But there are surprises there. When it was just the music site, our average user age was 38  older than you would expect. And the local symphonies have always been in our top 10 visited band pages on the site, indicating to me at least that there is less of a disconnect than you might think. Finally, we’ve had more user registrations in the past four days than we had in any month with TexasGigs. I think folks are getting it.”

A different, directory-oriented spin on the city site model is being taken by, a network of 24 hyper-local sites with a focus on events, business directories, and local arts and artists. Site Cofounder Ben Saren tells me he started the site because he couldn’t find “hours open” for stores in Coolidge Corner.

The site initially provided a free listing to every business in its neighborhoods and has a flat 25-cent pay-per-click rate. At this point, it has attracted 300 advertisers. Saren says the site previously experimented with pay-per-call. But the variable pricing was “illogical to most small businesses.”

To date, neighborhoods out of the downtown district do best, like Jamaica Plain and Harvard Square. “There is a lot more of a neighborhood mentality,” says Saren The more homogenized, high-rent businesses in downtown Boston are less likely to pitch their tent with a local city site.

Saren, like Pegasus’ Orren, hopes to take his concept beyond his city’s borders. “Ideally, it would be a Tier 2 or Tier 3 market with a college orientation, like a Burlington or Tallahassee,” he says.

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