The following is an interview with Brad Flora, editor of WindyCitizen.com, about the Real-Time Ad product they’ve launched.

Download Interview with Brad Flora of WindyCitizen re Real-Time Ads

Brad Flora explains in more detail how WindyCitizen.com came up with Real-Time Ads, how real-estate businesses were already coming to the site to try to promote themselves, and how they became determined to offer their clients something more useful than banner ads.

At about 8:05, we also have an interesting discussion about the future promise offered by doing more robust targeting of the ads, so better match the advertiser with the user by means of leveraging the personal user data that a quasi-social networking site like WindyCitizen.com can gather.

At about 13:30, we address how to strike the balance between too much control of the conversation on a site vs. allowing things to get out of hand. He talks about the “broken window” theory of policing the site of a niche aggregator.

At 18:00 we talk about how crucial it’s going to be for sites to have simple, self-service ways for your users to buy advertising and give you money. At about 26:10, we address the issue of whether or not Real-Time Ads could ever grow to the point where they would start replacing the revenues newspapers have lost to Craigslist.