Tomorrowland: How AOL’s Digital City Foreshadowed More Than the Future of Local

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As Aol prepares to dial in Verizon’s mobile growth, the acquisition milestone serves as a reminder of another property that once upon a time peppered the online juggernaut with scrappy, prescient and sometimes just kooky digital innovations: We called it Digital City.

A bold mid-‘90s foray into online city guides, at a time many were still figuring out how to get online, Digital City was a joint venture between the Tribune Company and AOL, and it was here that I started as editor of the Philadelphia outpost. The focus was on creating platforms for local content partners such as city magazines and weekly newspapers, in which the sales team could deliver value with banner ads, sponsored content — yep, “native advertising” —  and regional anchor tenants. (Oftentimes our poor sales leads would spend as much time explaining “online advertising” as they did selling, but that’s another story.)

And as it turned out creating and operating city guides for all major U.S. markets turned out to be something of a cover. What we were really doing was running a skunkworks project with few boundaries on creativity — where success or “failing-fast” were not the goals: Conjuring the new, the not-yet-done, the captivating that would hook and hold visitors was the point. AOL members visiting Digital Cities at the time were often presented with the future of AOL, and by extension a bit of the future of online interaction.

BBSs-to-Big Boards
My perspective was formed by years of participating in and writing about electronic bulletin board systems (BBSs), which were dial-up online services preceding the Web, AOL, Prodigy, etc. If I learned anything in those early days of online communities it was that the “users” were in charge. People dialing in and tapping away in clunky forums and chat rooms generated the most important content — their voices. Not much has changed in 25 years.

It was through this lens that I viewed AOL: A fast-growing electronic bulletin board where the people drove the content and the product innovations emerged a half-step ahead of where members were trying to go.

At Digital City we quickly realized that many features our visitors wanted (usually before they could articulate it) were simply not invented yet. I learned this in part by attending in-person parties thrown by members of local chat rooms, many of whom knew each other only by screen name, and by watching online behavior 16 hours a day — we had little automation at the time so we were manually slinging content and ads at all hours. Many months on that schedule and one tended to develop a sixth sense for what people truly desired after the modem stopped screeching.

Pics and Blogs
For instance, we knew members wanted to share and consume photos, particularly in the service of securing relationships of one kind or another — virtual and otherwise. Shockingly obvious today, but it wasn’t always. Digital cameras might as well not have existed, given their price and lack of availability, and the local copy shop was charging something like $5 to digitize pics. So we offered our members a deal: let us use your pics to fill our photo galleries where everyone could enjoy them and we’ll scan your pictures for free. Needless to say we were inundated — thank goodness for sharp interns.

When it became clear that people wanted their voices trumpeted on hot local topics as well (which sometimes went national, a la the 2015 incarnation of local news called Ratter), Digital City responded creating the first live polling mechanisms that clearly illustrated how every voice counted in real time. This led to an early formula for handling all hot local news: present the context of a story, usually gleaned from a local content provider like the city papers (or borrowed from a city tabloid), a changing live poll, photo galleries, message boards and something new borrowed from the Web’s “graffiti” boards, dubbed comment boards, which sat on the page below the story.

These boards were a new thing — a place to give knee-jerk, instant reactions to whatever the topic was. Often the members’ voices became the story as much at the story itself. It was the radio talk show where everyone could simultaneously be heard. And sports? DCI editors, particularly in the sports town of Philadelphia, created context for members to spend untold hours typing to each other about the latest controversies on and off the field. Digital City used the new platform and its access to provide members unprecedented, behind-the-scenes connections to players and coaches. The velvet rope was cut.

It brought out the best and worst in neighbors and they couldn’t get enough, frequently battling modem-to-modem into the early morning hours (AOL received plenty of complaints from people about their pre-flat-rate monthly bill!)

To acclimate people to come back frequently, we needed a model that provided local content updated every day, preferably multiple times a day. It was something our “information providers,” as they were called at the time, could not do. City magazines, weeklies and even local TV affiliates simply were not set up to provide fresh daily context — even the big local papers in many markets were not there yet. So from this emerged what would be known as blogging: We brought in local notables in the areas of sports, news, politics, etc. to write posts, tap to members in the message boards and host a live chat at least once a week. The formula worked, helping to get people logging in morning and night.

Getting Personal
On the lighter side, Digital City (DCI) tried many things that appealed to people’s emotional sides. Local personals was an obvious product, and one that proved incredibly popular for those looking for love nearby as well as those just browsing (usually far more of the latter). It was in this context that we tried developing early “geo-social” experiments that might match people based on triangulated locations and preferences, but much of that did not see the light of day in the U.S. for more than decade (read: Tinder, et al.).

And when the last updated profile was browsed we’d move members onto the next, related experience. These included products like “I Saw You” where people could type about missed local connections in hopes that person would read their appeal — many did); in our Philly office there was “Dumpadelphia,” where visitors would spend hours writing about how they were “dumped” or how they ditched a significant other; “The Confessional” gave people a place to anonymously post and read about, well, confessions; a widget allowed members to write missives that we’d deliver in Morse code, requiring a visit to our sponsored Relationships site for quick translation (hey, DCI editors never promised high-mindedness, nor a completely “local” focus). In fact, when we needed traffic to our sponsored health section we’d gin up gems like “Healthy Bodies” where members would upload pics of their buff bods for everyone in town (or any town) to admire. A little later we experimented with very early facial-recognition software with the intent to connect people based on desired physiognomical features, in addition to location and profiles, but AOL pulled that tech away in favor of a more practical implementation: fighting spam.

There were nascent Video Personals being trialed at DCI (again, this was 1997) as well as a local musician’s network where bands could upload their songs, a “Trading Post” that launched about the time of Craigslist, and “Name That Song” that served up a few seconds of a song from a local-notable band and asked members to guess the artist … and on it went, with deeply meaningful places for member interaction living alongside silly distractions.

Tip of the Spear
It wasn’t long before execs at AOL HQ took notice — some kindly, some with a sniff. AOL was going a 100 miles an hour in the late-’90s, and folks at the Dulles, VA headquarters  were taxed, to put it mildly. Process and bureaucracy had crept in, causing the rate of innovation to slow a bit. This was not yet so at DCI, where the naive belief was still “anything is possible,” if not probable, as long as a sense of wonder remained. Soon DCI was regularly creating localized features for AOL, or delivering products that both didn’t exist at the service and were magnets for usage. Not all flew, of course, like the online concierge service created for several cities in the DCI network. Members could type questions to a live concierge and have all kinds of services rendered on the spot. But the business model for a free concierge service could not support a national rollout and thus it was dropped. (Enter Operator 16 years later.)

DCI became the tip of the spear on broader innovations as well, delivering some of the first content and technology behind AOLbyPhone and becoming the first city guide available as an interactive service on early data-enabled cellphones — the first “Local App” you might say.

Eventually AOL bought out the Tribune and the DCI network of city sites was renamed AOL Local, with a focus on delivering core local content cities in every zip code. Innovation continued for sure, with a focus on providing members the quickest route to the best local information, but it was more about delivering an excellent and scalable commodity than keeping members engaged for as many minutes as possible (the initial model).

AOL broke ground on an unmatched scale before and after the spark of Digital City — much of it cloaked by its proprietary software, and thus lost to time as the Web and broadband surged. But for a few years, shortly after the emergence of online as a destination, little Digital City and its scrappy force of editors, producers and developers plunged headlong into the dark, emerging as pilgrims of a digital future that has finally arrived.

RickRRick Robinson is SVP of Product for on-demand roadside assistance startup He is also an advisor to Street Fight. Follow him at @itsrickrobinson