Hyperlocal 1.0: Matt Kursh Remembers Microsoft’s Sidewalk

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This is a the third installment in a series about hyperlocal past and present. Read here about Digital City / AOL and CitySearch.

A serious contender and moneyed innovator, Microsoft Sidewalk took to the local Web the way the behemoth did most things: with lots of muscle. It quickly squared off with CitySearch over advertising share and rapidly expanded its editorial footprint across the nation – carrying itself with arguably the most style among the hyperlocal contenders.

Microsoft’s Sidewalk at the top had 300 people going after the nascent local market. And it’s relatively strong run, before being sold to CitySearch in 1999 (now part of IAC), was marked by smart teams relying more heavily on what would become commodity data rather than an abundance of community voice. Still, Steve Ballmer, current Microsoft CEO said in a Herald Tribune article that called Sidewalk a wayward foray outside Microsoft’s software business, “… Sidewalk was really aimed at what we now call local search… Sidewalk is one we should not have gotten out of.”

Matt Kursh, GM of Sidewalk

Street Fight caught up with Matt Kursh who was there at the beginning and had a few insight to offer on the service, it’s goals and challenges.

When was Sidewalk conceived?
Matt Kursh: When I arrived at Microsoft in mid-1996, Sidewalk had been under development for a year or so.

What was the initial goal?
Matt Kursh: Our goal was to make Sidewalk the best destination for local content.  Though the founding vision was broad, the initial service was entirely focused on arts and entertainment coverage.

Though the founding vision was broad, the initial service was entirely focused on arts and entertainment coverage.

Early plan for Sidewalk in the mid-'90s, then called Cityscape. (Courtesy of Dave Chase, one of the first members of the Sidewalk team)

How much focus was put on delivering local advertising vs. local content (soccer scores and hyperlocal news)?
Matt Kursh: Sidewalk had advertising from the start, and we had a large sales force dedicated to selling it.  We felt that advertising was a highly-valued form of local content.

Were you more successful selling to national brands across the network or local mom and pops?
Matt Kursh: At launch, we were in about eight U.S. cities, so our footprint made it difficult to sell to larger chains.  Sidewalk 2.0 added yellow pages and a wide array of buying guides.  It also gained a national footprint overlaid with deeper content in larger markets.  This allowed us to sell to larger advertisers. Challenges: The standard issues – advertisers wanted exposure, and we were a new service.

What were some of the biggest challenges in those first years?
Matt Kursh: We grew out our city teams very rapidly and we had to quickly evolve the best ways of balancing the needs of the network vs. the competitive goals of a given city.  Most fundamentally, though, we knew we wanted to do “local”, but we had to figure out what that meant – just like everyone else!

When did you become aware of CitySearch / Digital City and were they competitive?
Matt Kursh:
We were always aware of CitySearch and Digital City.  It felt like Digital City was doing something very different from us, so they didn’t feel that competitive, but CitySearch was clearly running the same race as we were.  In the end, we felt like the arts and entertainment category wasn’t a good fit for Microsoft and we sold that part of the business to CitySearch, retaining the shopping-related categories for our future development.

How did Sidewalk overcome challenges of getting content across multiple city sites?
Matt Kursh: Our technical platform was always built to share content across the sites, so the big challenge was dealing with the editorial and cost issues.  For example, at launch each city planned to write its own movie reviews, but we quickly realized this was a cost redundancy with no value to readers.

What would you recommend to “hyperlocal 2.0” players starting out today?
Matt Kursh:
I think that the big challenge is often that you need to skip the “big concept” cliches – “local”, “social media”, etc. – and focus intently on delivering a very clear set of benefits to your customers.  Investors often bet on a team or a category, but consumers are only interested if they love your site.