When I graduated from Northwestern in 1995, I wanted to be a national sportswriter. Like, right then. I resisted the notion that I had to go off to some podunk town and cover JV volleyball and if I was lucky, in 20 years I would be a columnist at a newspaper.
And so I was living in Wrigleyville with my gainefully employed roommates, slowly sinking into a bit of a despair over my joblessness. At one point, I had an unpaid internship in the PR department of the Chicago Rockers of the Continental Basketball Association. I think I stuck around for two weeks before figuring that it wasn't really worth the effort.
In late October, I got a call from a friend in my journalism school's career center. She wanted to connect me with two Kellogg drop-outs creating a sports media company online (What's "on-line?")
I met with them in one of the partners' apartments. They explained that after a summer spent interning at AOL, they got some investment money from AOL, which was then growing for its proprietary service a network of original content sites, under the management of Ted Leonsis.
Their goal was to create the sports destination for this network. And while they were savvy b-school students and had a few ideas about content, they wanted fresh (perhaps code for "cheap") eyes from a person who understood content.
For me, despite having zero experience online (not many did), the appeal was obvious: Tons of creative control, reaching a national audience, writing about sports -- for starters, about college basketball, at the time my favorite sport.
Best and most important of all, the founders recognized that the way to go was to approach sports coverage from the perspective of fans -- this wasn't just a competitive imperative when competing with the ESPNs, SIs, Sporting News and newspapers of the world; this was a fundamental understanding of the dynamic between producer and consumer in the new medium. Remember: This was a couple years before Bill Simmons launched his Boston Sports Guy column on AOL. I give the founders -- and Leonsis -- an immense amount of credit for envisioning a fan-friendly approach to sports content.
And so I was being paid to write whatever I wanted about a sport I loved, however I wanted to -- in fact, with a mandate to write like a fan, not a stodgy journalist. It totally fulfilled the part of me that wanted to make an impact on journalism, to do something entirely new, whether that was the tone and voice of my writing, the engagement with users or the "always-on" news cycle.
It was a dream job.
The company was called, at first, "Extreme Fans." It was later changed to "Real Fans Sports Network." If you were on AOL back in the mid-90s, you hopefully remember it. (I think Leonsis would. One day, when I knew Ted was meeting with our co-founders, I led our home screen with tons of content about Georgetown hoops, because I knew he was a huge Hoyas fan.)
It was a crash-course in everything that mattered -- and still matters now, if you keep up with the current environment for start-ups: Being focused, running lean, constant iterations and feedback loops, engaging the consumers.
Remember that at the time, AOL was a subscription service: Its sites got paid based on minutes spent on each destination by users. And so the premium was getting people to come back a lot -- and once they were there, getting them to stay.
And so in addition to writing daily original individual game recaps for every major-conference college basketball team (I did half; Rob Peterson wrote the other half), we came up with ways to let the users contribute to the site's editorial coverage, which users did brilliantly. It was a very early but critical lesson in online programming: Trust the users.
I would like to think that my natural intuition was a big part of my successful contributions to the company, but I remain convinced that it was the constant at-bats, every day, in the company, that helped develop for me an intuitive understanding of successful online content.
Despite the fact that I spent less than a year there, it set the table for everything that would follow in my career. As defining as it was for me to get recruited away to the company running ESPN.com, my biggest regret was missing out on my first company's acquisition.
That was the AOL postscript: To follow up its initial investment, AOL acquired my company to make it the hub of its sports strategy. As part of the team, it is one of the most satisfying points in my career to take a smidgen of credit for it - offset by the fact that I left before my options were issued, let alone vested.
(To put it in the larger context of AOL's quarter-century history, AOL later made my company the hub of its revenue-generating "anchor tenant" strategy and, under that, AOL's first big money-making deal: In exchange for paying AOL millions of dollars to be its leading sports presence, SportsLine made AOL shutter my company. Absurdly, SportsLine didn't even try to get AOL to hand over my company as a content engine. It was, simply, kaput.)
And so on AOL's 25th anniversary, I look back with tremendous fondness on the pivotal role AOL played in my career. And as I plot out what's next, I find myself thinking a lot about that first start-up and how simultaneously thrilling, frustrating and satisfying the experience was.
PS: I could have written a Posnanski-style 7,000 words on this. To spare you, I limited myself to 700. Maybe I will revisit some of the bigger lessons in more detail at some point.