Microsoft Sidewalk

» see sidewalk.com as it lived, on the wayback machine

~ the eulogy ~

Sidewalk was Microsoft's pitch at owning the local web. The domain had been registered in 1995 by C.D. Bell of Los Angeles, Microsoft bought it in 1996, and the service launched in 1997 as a city-by-city portal with restaurant listings, event calendars, movie times, and a magazine layer of features written in a tone meant to compete with weekly newspapers like the Village Voice or LA Weekly. Microsoft wanted Sidewalk to do for local what Yahoo was doing for the directory layer.

The economics did not cooperate. Paying local editorial staff in roughly a dozen US metros at once turned out to be expensive, and the ad market for online local was not yet a real category. AOL had its own Digital Cities. Citysearch had a head start in the same lane and Ticketmaster had bought it. By 1999 the math no longer worked, so Microsoft announced on July 19 1999 that it was selling the entertainment-guide portion of Sidewalk to Ticketmaster Online-CitySearch for a combination of stock and warrants and taking a stake in the merged business.

The first time i heard of Sidewalk was years later in a Steve Ballmer interview clip. The product never crossed into Turkey. It was an American product covering American cities for an American advertiser base, written in the voice of an American weekly. By the time i had broadband and the kind of attention span that could have used a local-events portal, the category had collapsed into Yelp on one side and Google Maps on the other. Sidewalk lived and died in a window i had no view into.

~ the dossier ~

~ what it tried to be ~

Sidewalk's editorial bet was that the internet city guide could read like a real magazine, not a phone book with extra fields. The writing was hip on purpose. There were opinion columns, themed packages, neighborhood walking tours. The MSN brand sat on top because Sidewalk was an MSN product, but the city pages tried to feel local rather than corporate. For a couple of years the New York and Seattle and Boston editions were treated as legitimate alternatives to the print weeklies they were competing with.

~ what Ballmer regretted ~

In 2007, eight years after the sale, Steve Ballmer told an interviewer that Sidewalk had been pointed at what the industry by then called local search, and that selling it had been one of the things Microsoft should not have done. By 2007, Google was already turning local search into a real business through Maps and the place-listing layer underneath it. Microsoft's own attempts at local under the MSN and Bing brands kept falling short of what Sidewalk had set up to do a decade earlier. The regret was specific. Sidewalk had been an early local-search platform with real editorial weight, and Microsoft had treated it as a magazine venture.

~ what it left ~

The Sidewalk URL stayed under Ticketmaster Online-CitySearch and later passed through CityGrid Media and Ask Media Group with progressively thinner content. The actual lessons it left are not on that URL. They are in the gap between what Sidewalk was set up to be in 1997 and what local search became under Google in the late 2000s. Microsoft saw the shape of the market before anyone else did, then bailed before the market existed.

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