Persistence pays off in ‘real time’ for Windy Citizen

Persistence pays off in ‘real time’ for Windy Citizen

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Brad Flora

For Brad Flora, the smart Chicago Internet entrepreneur who founded the popular content-sharing website, the third time proved to be the charm.

On Wednesday, Flora was awarded a $250,000 grant from the Knight Foundation’s 2010 News Challenge to develop new uses of digital technology. It came after Flora’s third attempt to win a piece of the foundation’s prize money, which this year totaled $2.74 million.

“I’ve been told I’m one of the — if not THE — most persistent applicants they’ve ever had,” Flora said Thursday. The first time he applied in 2008 he hadn’t even finished his new media graduate studies at Northwestern University’s Medill School of Journalism.

Flora, 28, went on to launch‚ Windy Citizen just after he graduated from Medill in May 2008 and continued to operate and improve the site (which now bills itself as a “web service that lets people share their favorite Chicago news and events with their friends and neighbors”), all the while refining his pitch to the Knight News Challenge.

This time around, he hit the jackpot with his ingenious idea to develop and improve software for “NowSpots,” real-time ads as a way to help online startups become profitable. (“These ads are designed to be engaging as they constantly change — showing the latest message or post from the advertiser’s Twitter account, Facebook page or blog,” the foundation noted.) Said Flora:

“I have no insight into how the winners were picked, but this year’s group includes a lot of people who have already been working on these projects in some fashion and sought funding to take them to the next level.‚ In our case, we’ve been seeing success on a very small scale with our brand of real-time advertising.‚ Funding from the Knight News Challenge will let us spin that off and make these same sorts of ads available to publishers of all shapes and sizes at scale.”

Since news broke of Flora’s good fortune, he’s been inundated with well-wishers. “Response in the last 24 hours has been great,” he said. “People are signing up to our e-mail launch list.‚ I’m hearing from publishers and other startups.”

And no doubt from one or two job seekers as well.