Sidewalk: Insider's view of why & how it was killed (aka sold) and why Steve Ballmer now regrets it

I was one of the first dozen or so members of the Sidewalk team at Microsoft that swelled to over 300 at one time. Personally speaking, it was the best of times and the worst of times. In my dozen+ years at Microsoft, it went from being the strongest team I'd ever seen assembled at Microsoft to my first evidence of Microsoft being infected with politics and big company shenanigans. In the 12 years or so since Sidewalk's inception, I've yet to see an accurate story of what really happened with Sidewalk. The local newspapers who reported on it not only didn't have an inside view but they also had a clear agenda to cheer Sidewalk's demise (e.g., the Seattle Times would never even publish Sidewalk's name). The industry trades simply took the story that was spun by Microsoft's PR and didn't dig deeper. Even astute industry commentators like Jeff Jarvis, Tom Evslin (an ex-Microsoftie), Frank Barnako, Stowe Boyd, Dan Gilmor and Fred Wilson, who often comment on the local Internet scene, aren't aware of some of the sordid history of Sidewalk.

I hadn't thought much about Sidewalk since I left that team in late '97 after spending a couple years on the team. However, a few things have brought back those memories and I thought people might find it instructive or at least somewhat entertaining to hear the story and share some perspective on the application of those lessons in today's web environment. It also shows how hard it is to incubate a new business inside of a behemoth corporation given the lack of patience that is often exhibited.

The following is an excerpt from a recent Herald Tribune article:

In 1999, Microsoft sold Sidewalk, an online city guide service. It seemed a wayward foray outside Microsoft’s software business at the time. “But Sidewalk was really aimed at what we now call local search,” Mr. Ballmer says. “Sidewalk is one we should not have gotten out of.”

Sidewalk was purchased by Citysearch in 1999 which is now a part of Barry Diller’s empire (along with Expedia, also started by Microsoft...he tried to purchase other Microsoft assets but that's another story). I recently had the pleasure of meeting Charles Conn (founder of Citysearch). Coincidentally, we now live in the same town and are on a non-profit committee together. Though I’d never met Charles, I was very aware of who he was (one of my Sidewalk colleagues had been a McKinsey partner with him) and we always had respect for Citysearch as a strong competitor that had some innovative go-to-market approaches. After sitting down for a coffee with him and sharing some battle scars, I realized that as the acquirer of the business, he’d gotten spun a good story that didn’t mirror reality yet that story is what is broadly understood to be the “real” story about Sidewalk. The reality is quite different although Charles shed light on things from Citysearch's perspective which was enlightening.

I realize that describing what led to Sidewalk’s demise is a bit like a blind man describing an elephant. There are several perspectives but I had a pretty well rounded view not only from my own experience but that of several people in other parts of the organization that stuck around longer than me. I jumped off what I saw was a sinking ship when I got the opportunity to fulfill a career goal of being a general manager of a business at Microsoft (Encarta.com).

One of the impressive things about Microsoft is its patience and determination. However, this tends to apply to traditional technology businesses (e.g., Windows and the Server businesses for Microsoft took ~ 10 years to pay off) versus the customer side of the business or media businesses that it has yoyo’ed in and out of. If I had a nickel for every time I heard Ballmer, Gates et al say “we aren’t in the media business”, I’d be a very rich man. I always felt this was naïve or disingenuous and would say to others “if it looks like a duck and quacks like a duck, it’s a duck”. Ballmer was quoted in the Herald Tribune article as saying “One of the biggest mistakes I’ve made over time,” he acknowledges, “is not wanting to nurture innovations where I either didn’t get the business model or we didn’t have it.” I saw this in a previous role when I was one of the first two people in Microsoft doing vertical industry marketing. Ballmer would ask us, "why don’t you guys handle more than one industry per person" when we’d grown to all of eight industries (e.g., I started Microsoft’s healthcare business). We’d just shake our head when we knew our competition had anywhere from 20 to 300 times as many people tackling each industry as we did. Thankfully, Ballmer finally got it when he saw how much money we were bringing into the company with this approach (last I heard, the healthcare industry effort I started was ~$500M in annual revenue). Believe me, when Ballmer gets something watch out as he is wicked smart and relentless...it just takes awhile. The successor to that vertical industry marketing org now has 2,000+ people in it. Unfortunately, it was going to take Sidewalk a lot longer to bring in positive cash flow as it had large product development costs (and this was known from the get-go).

When the original “founders” of Sidewalk pitched their business plan to Gates & co, there was an expectation that we’d sink $500M before making a profit but that we were building for the long haul and that the $67B or so spent on local advertising was a prize worth going after. Unfortunately, a few factors transpired to prevent that vision/plan from being realized. At the same time, MSN was a complete cluster*&$# and was hemorrhaging money with some failed experiments such as Bob Bejan’s “shows” that were about 10 years ahead of their time and countless other wacky content plays such as “Microsoft Dogs”. Meanwhile Sidewalk was hemorrhaging money (as planned) and there were many other media/e-commerce plays that were driving the senior execs crazy particularly when some of the them presented conflicts with corporate customers. These customers threatened to stop buying Microsoft software if Microsoft didn’t kill or spin-off some businesses (e.g., a key reason Expedia was spun out as it was an irritant to major corporate customers such as United Airlines). Barry Diller , Charles Conn and others were savvy enough to realize there was some "throwing the baby out with the bathwater" effect when Microsoft was trying to get out of content oriented businesses (some it later had to duplicate investment in later such as in Entertainment, local search, etc.).

Around this same time, Microsoft had acquired a company named eShop for the technology that became Microsoft Merchant Server. eShop also had “eShop Plaza” that came along with the deal and became MSN Shopping which was part of the still-flawed model of “online malls”. Nonetheless, one of the founders of eShop (Matt Kursh) was enamored with his “online mall” and wanted to fulfill his vision of being the predominant “online mall” on the web (to this day, MSN Shopping is a 2nd or 3rd tier shopping site that has had, at best, modest success). However, Microsoft had no intentions of staffing that in a way to win on the web. As I recall, for a long time, eShop had one employee and a contractor or two who heroically kept the thing going. Meanwhile, the technology guys (Will Poole and Arnold Blinn) were what the Merchant Server product team wanted so Matt was put into a staff position working for John Neilson who oversaw Sidewalk, Expedia, Carpoint, and HomeAdvisor. Unfortunately, at a critical juncture in Sidewalk's history, its executive champion (John Neilson) was tragically struck down with non-Hodgkin's lymphoma. John was a phenomenally talented guy who was inspiring to work for and also happened to be good buddies with Bill Gates (e.g., in Bill's wedding party) and Steve Ballmer. There's no doubt he'd be one of the three Microsoft presidents now given his talent, passion and connections. On a personal note, the day I was finalizing my new role working for John in a role that spanned his four businesses happened to be the first day he was out "sick" (I later learned just how sick he was when he didn't come back).

Matt Kursh came into lead Sidewalk at a time when his dislike of content businesses such as Sidewalk was consistent with many senior execs such as Ballmer who were questioning why we were doing content. From Matt's perspective, there could then be a happy coincidence of cutting costs on content businesses and make the case that some of those resources should be redirected towards the online mall concept. The fact that Amazon.com was in Microsoft's backyard probably made the shopping angle that much more attractive vs. media businesses where Bill, Steve and others had no experience. It should also be noted that the online ad business hadn't matured to where it was clear you could make a boatload of money.

Sidewalk had a super strong group of city General Managers such as Kevin Eagan, Cella Irvine, Doug Heinrich, Chris Hearne, Anne Karalekas, Moya Gollaher and Brad Struss. They had all gotten past what was the toughest interview process I’d seen of the legendary Microsoft interview process. It was Microsoft’s heyday and it could basically get anyone it wanted to join the company. One of the key premises that Frank and the founding team of Sidewalk had was that Sidewalk was going to experiment like crazy and let these high-powered GMs have a lot of freedom to innovate. This led to a natural tension between Redmond and the cities fighting for who controlled what decisions (Redmond product people were used to having the final say on all product decisions). Having now worked with many startups, Matt was typical of many entrepreneurs I’ve worked with who by the sheer force of will, they succeed. Implicit in this is they have a group of people who rally behind them to pull it off. Matt didn’t have this advantage at Sidewalk where you could get people to rally behind you as the city teams and many in Redmond were deeply skeptical of him and questioned his understanding of the local/media business where he had zero experience. This led to the Redmond vs. cities war to escalate.

Just prior to Matt taking over, one of the least pleasant things I had to do in my career was shutting down the Montreal Sidewalk office which Frank had decided to do. While it wasn’t pleasant, I 100% agreed with the business rationale. I was on point to ensure that it went smoothly from a human resources and PR perspective. It wasn’t a career highlight but I was told afterwards that it was the most successful “RIF” (reduction in force) that the company had gone through. The RIF’ed employees were treated well, there was barely a PR blip, etc. My reward? When Matt took over, he was familiar with what I had done and basically offered what I viewed as making a deal that was at odds with my beliefs. I would take over management of all of the cities (I was managing half of them at the time) with the goal of progressively reducing the city teams to non-existence. In exchange, I would take over a substantial portion of the product team. It was the first time in my career where I had an explicit fork in the road where I could either be true to myself and what I believed made business sense (Ballmer's comments provide a measure of vindication on that front) or maximize the opportunity for promotion by being someone's hatchetman. To that point, getting rapid promotions was my primary career goal and it had worked very well for me. Ultimately, I politely declined the offer. The guy who took on the responsibility I declined became the GM of MSN Shopping. He’s a guy I like a lot but didn’t have the issues I had with killing off the city teams and was rewarded handsomely for bleeding the cities.

Matt felt he had to reign in the cities and the pendulum swung from decentralization to centralization. Some of the GM’s such had creative ideas that were money-making ideas they’d teed up in their market, however most of those ideas were killed. The byproduct was constrained revenue growth and innovation which made the case even more solid why Sidewalk should be eliminated. The case became even stronger when acquisition discussions with Citysearch were enthusiastically pursued . This would free up resources to redirect towards MSN Shopping and recoup some of the investment Microsoft had made in Sidewalk via the acquisition. To his credit, the corporate development team played their hand well as the Citysearch guys knew there were issues inside of Microsoft regarding Sidewalk but not the extent of those issues and had little idea that they didn’t have to buy Sidewalk to eliminate a competitor. The Sidewalk acquisition increased the attractiveness of Citysearch’s stock (Ticketmaster Citysearch went public December 8, 1998) and has gone on to success.

The stated purchase price for Sidewalk was $240M, but $150M of that was in a clever warrant security the Citysearch guys called the "weedwacker". This warrant was designed by BD's vice chairman, Victor Kaufman, and it had a strike price that decreased as the value of TMCS stock increased, potentially delivering huge value. But it expired unexercised when the bottom went out of the market (TMCS' stock declined to $14 at one point in the crash, well above their IPO price, but below the trigger point for the warrant). In the end they paid less than $100m for Sidewalk and once again Barry Diller et al saw the value of properties that Microsoft didn't.

Postscript: Several members of the original Sidewalk team went on to become successful CEOs outside of Microsoft while a few of them stayed at Microsoft. I worked with many great people during my Sidewalk tenure who have gone on to great success in and out of the work world. Google people like Michael Goff, Richard Tait, Frank Schott, Laura Bordewieck (later Rippy), Jan Even, Mike Gordon, Dan Fisher, David Harrington, Gayle Troberman, Peter Atkins, Cella Irvine, Peggy Brown, Bill Furlong, the aforementioned city GMs and many others and you’ll see that the caliber of the team was amazingly high. It’s too bad Ballmer didn’t have more patience for that team to realize its full potential. In fairness to Steve, he was sold a story that he bought that wasn’t the complete picture of Sidewalk, however he was very open to hearing that story. Microsoft’s Internet business would be in much better shape than it is today as that talent largely left the MSN arena or the company altogether.

As for me, I dipped my toes back into the local online space last year becoming an investor in SunValleyOnline.com (a local news and information site for the Sun Valley area resort community).To my knowledge, SunValleyOnline is one of the few local online properties anywhere in the country to be making money (e.g., Citysearch is now making a profit) and is applying many of the lessons (good and bad) from Sidewalk. For example, the web user of today is much more willing and able to contribute content to a site if the right tools are in place. If you check out a site like SunValleyOnline, you'll see that 3/4 of its content are provided by the community it serves. SunValleyOnline can also leverage off-the-shelf tools rather than have to build much of the technology on its own (it still has to have some proprietary tools but far from 100%). Whether it is leveraging blogging software (WordPress) or utilizing infrastructure of others (e.g., YouTube), it can bring new tools to market rapidly. Let me share one example of the power this has had in the greater Sun Valley area.

Blaine County is the county that Sun Valley is in. For 17 years, Blaine County had tried and failed to get a new jail built including 3 failed jail bond elections. A jail bond election took place earlier this month. Prior to the election, the Sheriff and County Commission Chairman were reaching out to the local media in an attempt to raise awareness of the issues regarding why a new jail was needed (the list was long and compelling). Traditionally, if you tried to win an election in Blaine County, there were the typical tactics (newspaper ads, letters to the editor in the newspaper, etc.). SunValleyOnline (SVO) suggested a different approach leveraging the tools of the citizen journalism movement. There were two tools in particular that were suggested to the sheriff and commissioner that they took advantage of.

1. Video. The sheriff and commissioner offered to give tours of the jail to any citizen who wanted as he knew that anyone who saw the conditions his people worked in and the liability exposure the county had would vote for the jail bond. Realizing that very few people voluntarily want to go into a jail, SVO suggested shooting a video tour and posting it on YouTube/SVO. In other words if people won't go to the jail, take the jail to the people. It was far from a Spielberg production but it got the point across.

2. Blog. Naturally, voters had lots of questions about the true need for the jail and there were some conspiracy theories about the jail (e.g., it was going to enrich the sheriff) that they wanted to explain. As a voter who was neutral on the vote, I had several questions so I offered to post the questions in my blog I had about the jail. This spurred a tremendous dialogue between citizens and the commissioner answering questions, responding to rumors, etc.

The ads the jail bond campaign purchased on SunValleyOnline simply pointed to the videos and blog.

The end result? The jail bond passed overwhelmingly with nearly 80% of the vote. The sheriff credited the video tour based on the large number of comments he got as he was out in the community. It was apparent from the comments on the blogs that people who'd previously been against the jail bond changed their vote as well. The cost of using the aforementioned tools was negligible yet it had a demonstrable effect on the community. These are the sorts of things that weren't feasible in the early days of Sidewalk.

I searched my hard-drive for some of the early Sidewalk documents (back when it was still code-named "Cityscape") and found the original business and product plans. It's interesting to see how the opportunity was described and what the product vision was. Had Microsoft stuck to the plan and let the talented team pursue the opportunity, things might be very different today. Here are a few excerpts...

"We intend to play a similarly trusted role as the yellow pages and newspapers do today in consumers’ lives, by being the first best to look for an answer or a purchase. By developing a loyal set of consumers, we will create the best online advertising vehicle for local merchants and national advertisers, and capture a portion of the $67 Billion local advertising opportunity."

"To reach the comprehensiveness described above we expect will take 6 years." The reality is the plug was pulled in essentially 2-3 years before the yellow pages/local search opportunity could be tapped and before user-generated content became mainstream and would have made the cities far more cost-efficient (something Citysearch figured out) not to mention being able to do what I'd originally been hired to do -- scale Sidewalk in more efficient ways a la TV networks/affiliates after gaining insights from the so-called "owned & operated stations".