Almost exactly five years ago, I went out to lunch with my old friends Mark Bailey and Andy Karsch, and somehow over the course of our meal I got to talking about this idea I'd been harboring for several months about building some sort of web service that would organize local bloggers by neighborhood and zip code. By the end of the meal, Andy and Mark had convinced me that I should try to build a prototype, and had offered up seed money and other help to get my little hunch off the ground. Within a month or two, I found myself actually sketching out a user interface and talking database structure with two exceptionally talented ITPers: John Geraci and Cory Forsyth. By the end of the summer, we'd built a working version of the service and decided on a name: outside.in. The first public beta went live in October 2006.

Last Friday we announced that outside.in has been acquired by AOL, joining forces with their hyperlocal network, Patch.

It has been a fascinating, humbling (in both senses), exhausting and exhilarating ride. I served as CEO for about a year and a half, and built up an incredible investor base, with a mix of smart and supportive angels like Richard Smith and George Crowley, and wonderfully engaged venture investors: Union Square, Milestone, Betaworks, and Village Ventures. Working with Fred Wilson over the past four years has been one of the great experiences of my entrepreneurial life; he is even better up close as an investor and partner than his already stellar reputation would suggest.

A few weeks after I had somehow convinced the Board that I could continue as CEO and still write The Invention Of Air, I was introduced to Mark Josephson, and after twenty minutes of talking to him on the phone, I knew he would be a much better leader for the company in its "grownup" phase. It's not easy for a new CEO to replace a founder in the role, but somehow Mark did it with real grace and skill and good humor. I can't wait to see what he and the team build at AOL.

In the end, we built some powerful tools for organizing and curating local content at outside.in; hundreds of traditional media companies have used our platform to share neighborhood news and conversation with their audiences. (We continue to power the local news on the front door of CNN.com, a great milestone for our little startup.) As a business, though, outside.in was never a runaway success, and part of that stemmed, ultimately, from the limitations of a purely algorithmic approach to organizing local content. The best solution, we've come to realize, is a hybrid model that brings together all the existing sources of local information from the around the web, and uses it to support and augment original reporting and commentary. And that is the beauty of the AOL/Patch deal. We have the automated platform and they have the neighborhood-level journalists. For several years now, we've been watching each other, with some mix of competitiveness and admiration, but as we were announcing the deal, I realized that outside.in and Patch were just following the old romantic comedy script: "When are you two crazy kids going to realize you need each other?"

My favorite part of this whole experience, though, has been the people I've worked with over the past five years: some old friends, like Mark, Andy, and Bo Peabody; and dozens of new ones who worked at OI; all the twisted conversations on our endlessly amusing group list, [email protected]; our "hipster army" days in Brooklyn and our more professional Flatiron digs. I told the team last week when we announced the deal that founding a company and watching it grow in all these surprising new directions was the closest thing I'd experienced to building a family. The thing is, except for very rare circumstances, you almost never get the opportunity to sell your family to a large Internet company. So this is a new thing for me.

Since they are family, I'm not just waving goodbye as they join the good ship AOL/Patch. I'm going to stay involved in some capacity. I remain as committed as ever to the importance of bottom-up, hyperlocal journalism, and the opportunity to continue exploring that vision with the resources and audience of AOL behind us is too great an opportunity to watch entirely from the sidelines. But clearly, this is the end of a chapter, and thus worth pausing to thank everyone who helped make this one of the great adventures of my life.