Image via Marvel Comics

It was 1995 and Kevin O'Connor was sitting in a basement in suburban Atlanta with Dwight Merriman trying to figure out how to build a business on this new thing called the internet.

"We thought maybe car sales would be big. We figured porn would be huge, but we didn't want to get into that. Eventually we settled on ad sales," says Mr. O'Connor, who along with Dwight Merriman and Kevin Ryan, would go on to build the DoubleClick dynamic ad serving technology that became Silicon Alley's biggest exit and the engine behind Google's profits.

But it almost didn't happen that way, says Mr. O'Connor, who is currently hard at work on FindTheBest, a comparison engine that hopes to combine his deep experience with algorithms and the strength of the social web to provide a service that can help users pick the best private school, find the right netbook and avoid a nasty hotel on vacation.

Mr. O'Connor and his partner Mr. Merriman built the technology for a dynamic ad serving platform in Atlanta, but in 1996 they moved to New York to be close to the action and merged with a local agency called DoubleClick. "We were called the Internet Advertising Network, so clearly they had the better name."

At first times were tough. "At a lot of meetings with ad folks from traditional industries, if you told them the internet was a big opportunity, they just didn't believe you. They thought it was a fad."

By 1997, however, the tide was turning. "Greg Koerner, one of our early sales guys at DoubleClick came to me, he was just shocked. He said, 'Clients are calling me asking to buy ads. That has never happened to me before. I call them, and most of the time they say no.'"

At this point, a large portion of DoubleClick was owned by monster ad agency Bozell, who had cut the young company what was essentially a blank check to scale their technology as quickly as possible. Bozell was interested in selling while the market for dot-com related firms was hot. A number of firms were interested in purchasing DoubleClick. One of the most serious bidders was Yahoo.

"It would have changed the course of internet history," says Mr. O'Connor. At the time Yahoo was still king of search, with its curated portal of links. "They were a top dog then, not an ailing firm. But we were having too much fun and didn't want to sell out." Eventually DoubleClick obtained $80 million funding from Greylock and Bain, allowing the founders to continue running the company and giving them the capital to win in what Mr. O'Connor describes as, "One of the biggest land grabs in history."

As Yahoo struggles to redefine itself as a media company and Google continues to expand its advertising empire into the mobile sector, it's fascinating to look back and imagine what would have happened had thing played out differently. Let us know your thoughts for how this episode of "What If?" would end had Yahoo bought DoubleClick in the comments.

Yeah, dude, they totally saw that Facebook pic.

Back in June, Commissioner Ray Kelly revealed that the NYPD is just as likely as your ex-boyfriend to troll Facebook to see if you've been up to anything bad, at least the public events page. “We look at social networking. We’re very much focused on weekend parties,” said Mr. Kelly. Now, it seems, they've made it official.

Fresh off the heels of the Catch a Looter Tumblr that attempted to out rioters using political strife as an excuse to get a new iPad (or in some cases what looks like a Tanqueray bottle), The New York Post reports that the police have formed a new unit social media unit "to track troublemakers who announce plans or brag about their crimes on Twitter, MySpace and Facebook." In London, rioters have been using both Twitter and BlackBerry messages to find targets and outwit the authorities.

It looks like the NYPD is pretty serious about it. They've tapped one of the departments "online and gang gurus," Assistant Commissioner Kevin O'Connor, to be in charge of the "new juvenile justice unit." (Congratulations, olds! You're free to do as you please.) Mr. Connor has successfully used social media to catch actual criminals (as opposed to hard parties) in the past. If you see a friend request from him, you know what to do.