On August 7th of last year, Crain_’s ran an article about SketchFactor, an app that was set to launch the next day. It would allow users to report having seen or experienced something “sketchy” in a particular location; these reports would then be geotagged and overlaid on a Google map, creating a sketchiness heat map of a neighborhood or city. The idea was to help urban walkers be more street-smart, but the implications seemed insensitive at best, racist at worst. Allison McGuire, the app’s co-creator, had recently moved from Washington, D.C., to the West Village. Both she and her co-founder, Daniel Herrington, were white and in their twenties. At one point, the Crain’_s reporter asked McGuire whether her company “could be vulnerable to criticisms regarding the degree to which race is used to profile a neighborhood.”
“We understand that people will see this issue,” she said. Still, she argued, “sketchy” can mean many things. “As far as we’re concerned, racial profiling is ‘sketchy.’ ” She was confident that the app would reflect her good intentions.
A few hours later, Gothamist published a more pointed piece, under the headline “Tone-Deaf App Helps Naive Travelers Avoid ‘Sketchy’ Neighborhoods.” McGuire didn’t mind. “We were just excited to be mentioned somewhere else,” she told me recently. “Then I started getting texts and e-mails saying, ‘Have you seen the front page of Gawker?’ ” The headline there was more blunt: “Smiling Young White People Make App for Avoiding Black Neighborhoods.” There was a photograph of McGuire and Herrington, back to back, grinning. It probably didn’t help that the app’s icon was a black bubble with googly eyes.
The writer Jamelle Bouie tweeted, “Are you afraid of black people? Latinos? The poors? Then this app is just for you!” Maxwell Strachan, writing for the Huffington Post, pointed out some of the problems with establishing a “rating system based on the personal views of Americans, a people historically known to mask the occasional racist view behind words like ‘dangerous’ ”—or, for that matter, “sketchy.” Many people pointed out that the app, which was ostensibly designed to “empower everyone,” would, in practice, empower only people who owned smartphones. SketchFactor’s Twitter feed was inundated with such hashtags as #racist, #classist, and #gentrification. The next day, the same journalist at Crain’s wrote an article about the Internet’s “full-throated condemnation” of the company. “I was in shock,” McGuire said. “And the app wasn’t even live yet.”
SketchFactor never fully recovered. Businesses are path-dependent—what happens early has a disproportionately strong effect on what comes later—and this is especially true of businesses that rely on user-generated content. Unlike, say, a Web publication, whose tone can be set by its writers and commenters, the tenor of a social platform is largely determined by who is doing the socializing. SketchFactor was unexpectedly popular—it was, for a time, the third-most downloaded navigation app, behind Google Maps and Waze—but many of its first users were drawn in by the controversy. Some early “sketch reports” were actually pleas for the app to be taken down. Others were jokes (116th and Broadway: “pretentious undergrads”) or incomprehensible clutter (Atlanta: “This’s guy just kicked his dog ahhhhhhhhhhh”); still others were puerile outbursts or racist screeds. McGuire and her team encouraged users to downvote or report offensive posts, but they couldn’t remove them fast enough. Whether the idea was inherently racist or not, the app began to seem irredeemably toxic. The company released an update the following week and another one in October, but by winter they had stopped working on the app. In February of this year, they acknowledged that SketchFactor was not going to succeed. They decided to pivot.
Like “disrupt” and “10x” and “culture fit,” “pivot” is an overused bit of tech-world jargon; but it’s also a useful word with a simple definition. Let’s say you try to start a company and the idea doesn’t take hold, as most ideas don’t. You can disband the company. Or you can keep your staff and some key part of your idea, jettison everything else, and rebuild. This is a pivot (though a better term might be “flatworm,” after the invertebrates that can be cut in half and then regenerate themselves). In 2005, Noah Glass and Evan Williams launched Odeo, a podcasting platform. The next year, they pivoted—Glass and Williams stayed on, but they worked on new platforms that had nothing to do with podcasting. Eventually, they changed their name to Twitter.
Most companies pivot when they receive too little attention; SketchFactor’s pivot came after receiving too much negative attention. In February, McGuire changed her company’s name. (Had SketchFactor been named more innocuously in the first place, it might have attracted a different kind of audience; then again, it might have attracted no audience at all.) She and Herrington hired new staff and rebuilt around what she claims was always her core proposition: making city streets more walkable.
As of today, SketchFactor is gone. The new app will be called Walc. It recently closed a half-million-dollar round of seed funding, and it will launch in the fall. In the new app, users will not be asked to submit reports, and sketchiness will not be mentioned.
Tech entrepreneurs like to talk about failure, but they usually do so in the gauzy, uplifting tone of teleological hubris. Successful entrepreneurs fail up. They fail better. They move fast and break things. Starting a company is difficult, but the travails that befall a founder—the “trough of sorrow,” for example—are mere way stations on the path to glory.
McGuire bristled at the suggestion that her company’s pivot was a concession to public criticism. “We realized that we had built a social platform, and what we wanted to build was more of a utility,” she told me. “So we corrected. It’s that simple.” She did not express any self-doubt, and she gave little credence to the notion that SketchFactor was racist. “I’ve only ever been about helping people,” she said. “The fact that we were misconstrued was really painful for me.” I asked whether she had ever considered moving out of the West Village—say, to Brooklyn, where “sketch reports” were more plentiful—to field-test the app, or to see how locals responded to it. She said that she hadn’t.
When we spoke, in June, she referred to SketchFactor in the past tense; but it was still live in the Apple, Google, and Amazon app stores. Hundreds of people had downloaded it since February, and sketch reports continued to trickle in, like graffiti in a ghost town. I asked her why she hadn’t removed the app. After all, it was not generating income—it cost nothing to download and contained no ads—and she did not plan to transfer SketchFactor’s user data to Walc. Ed Smith, an entrepreneur who has launched a handful of major apps including the ride-sharing service Sidecar, told me that, if he were in a similar situation, he would take down any dormant app that had the potential to “hurt my brand.” This is a “very simple” process, he said. “It can take just a few moments.”
McGuire’s explanation, essentially, was carelessness. “As soon as we decided we were pivoting, we just didn’t touch SketchFactor at all. It takes time and energy and resources to do anything—editing it, pulling it, whatever. Our focus was on Walc.” In general, entrepreneurs who are moving fast and breaking things are not always equally concerned about cleaning up after themselves.
As I talked to McGuire, I tried to gauge how chastened she felt. Was her pivot only an economic decision, or was it also an ethical one? Did she think of herself solely as a victim of cyberbullying, or could she understand why her critics saw her as a perpetrator of it? Those questions seemed to rest on another: was SketchFactor just a failed business, or had it caused enduring harm?
One Friday a few weeks before my interview with McGuire, I walked through Bedford-Stuyvesant, a traditionally African-American neighborhood in Brooklyn that is undergoing rapid and contentious gentrification. I had SketchFactor open on my phone. On the map, my route was riddled with red bubbles, indicating a five on the app’s one-to-five “sketchiness” scale. When I found myself at a location corresponding to one of the bubbles, I approached the people near me, showed them the map on my screen, and asked for their thoughts.
Location: Nostrand Avenue at Myrtle Avenue, near the Marcy Houses
Sketch Report: “Same guy asks me about once a week to buy milk for him, follows me for a bit. Feels threatening.”
Early afternoon. No beggars in evidence, lacteally inclined or otherwise. Instead there were, from east to west: a Duane Reade; a deli; Lucky Liquor & Wine; Brooklyn Cooperative, a credit union; and Brooklyn Stoops, a new-looking burgers-and-beer place. Four middle-aged women waited for a bus. I showed them the app. “This corner ain’t so sketchy,” one of them said. “You want sketchy? Go down to Marcy and Greene. Don’t tell them I sent you.”
A young woman named Lupe Chino walked by, popped out her earbuds, and wrinkled her brow. Her companion Terrence Harper, a young man wearing a Billionaire Boys Club T-shirt, said, of the app, “Theoretically, it sounds good. If my friend tells me someplace is sketchy, I might listen. But a stranger?”
A man in his fifties, wearing a chocolate-colored chef’s apron, walked outside and introduced himself as Chef Jay, the proprietor of Brooklyn Stoops. “I know these people,” he said, gesturing toward Chino and Harper. “They come in all the time. I know they’re good people. But if you just look at an app and it says ‘sketchy,’ you’d just avoid a place without going to see it for yourself.”
Chino and Harper headed inside the restaurant. Chef Jay continued: “I’m from Harlem. I have four restaurants. I targeted this location a few years ago because I know this neighborhood is coming up. To me, an app talking about sketchy places? That’s basically judging people before you know them, which is pretty much the worst thing you can do, in my opinion. People can go on Yelp and find out whether I make the best chicken in this neighborhood. Which I do, by the way.”
Location: Nostrand Avenue at DeKalb Avenue
Sketch Report: “Lots of people making up stories on sketch factor and trying to annoy other races.”
An awning on the northeast corner: Sugarhill Supper Club, Restaurant & Disco. Up a flight of stairs is an old-fashioned ballroom: mirrored walls, a grand piano on a raised stage, a framed photo of Hillary Clinton with her arm around the owner. Dawn Albert, the manager on duty, said, of the app, “That is not a good idea.” She raised an eyebrow. “We’re not on there, are we?”
A few blocks south is The Civil Service Café, a smartly appointed coffeehouse with rough-hewn wood tables and a Strada MP espresso machine. Behind the bar, the owner, Ayo Balogun, held a piece of pound cake in his hand. “Does this place look sketchy?” he said. “I’m eating cake.” He looked at SketchFactor and scoffed. “Look, I’m conflicted,” he said. “I’m a black guy. I understand why this kind of thing is offensive. But I also own a business that caters to hipsters.” The app could, in theory, be good for business, signalling that the area is safer than it used to be. “Obviously, you hate to see the old-school, politically driven, redlining kind of gentrification. I’d like to think that what’s happening here is a less aggressive, more organic process.” He shrugged. “I moved here from Chelsea, so who am I to talk?”
Location: Herbert Von King Park, Marcy and Tompkins Avenues between Lafayette and Greene Avenues
Sketch Reports: “I’ve been solicited several times to buy drugs in this park, and in the mornings the recent ex-cons collect here to do pull ups on the playground equipment.”
“A little Hispanic girl threw a socket wrench at me while I was jogging. She didn’t want any white people playing in her park.”
Every Friday afternoon, on the corner of Marcy and Lafayette, at one of the entrances to the park, an anarchist collective called In Our Hearts gives away clothes, books, and kitchen supplies. Lisa Weir, one of the volunteers, sat in a portable lawn chair. She wore a jean jacket, bright green socks, a nose ring in her septum, and a loose Afro shaved on the sides. “Look around,” she said. “I’m in this park multiple times a week. I see people walking their dogs at the dog park. I see people teaching yoga classes. Is that sketchy? Look, I understand that now everyone wants to move here, and they’re right—Brooklyn is dope. But for them to come from wherever and immediately start judging what goes on here? I would ask them this: what’s sketchy, thirty black people on a corner, or six squad cars on a corner? I might have a different answer to that than Al from Seattle would.”
An S.U.V. parked nearby. A woman got out, crossed the street, and kissed Weir on the cheek. “Namaste,” Weir said. The woman handed her a wad of cash, ran back to the car, and drove off. “See, she owns a restaurant, and I’m a bike messenger, and I just did some work for her,” Weir said. “What if you didn’t know that? Would that seem sketchy to you?”
I strolled through the park. Tiff Baldomero, a young woman with a tight ponytail, waved her hand dismissively. “Frankly, if people want to be worried about this neighborhood, that would be great for keeping my rent low.”
Lisa Weir jogged past me. “African-American female running through the park!” she shouted. “Sketchy!”
In our interview, I asked McGuire where SketchFactor had gone wrong. “Was there anything you could have done differently?” I said.
“Was there anything that I could have done differently?” she said. “To make Gawker not write what they wrote about me? No. I have no control over Gawker.”
I pointed out that the headline had referred to “Smiling Young White People”; if her co-founder had not been white, people might have seen her company differently. She changed the subject. Later, she said that, before she met Herrington, she had planned to found SketchFactor with two female friends. “One of them is gay and one of them is black,” she said. “We all had our own experiences, our own ideas about what we wanted to help people avoid in the streets.” I was surprised. I had read everything I could find about SketchFactor; if the company’s origin story included two other co-founders, this was the first I was hearing about it. I asked McGuire several times to share their names, or to make them available for comment, but she refused.
Some of the people I met in Bed-Stuy, and others on Twitter, had suggested that SketchFactor was a cynical attempt to profit from bigotry. It seemed to me that McGuire’s motives were innocent, or that she thought they were. Still, inadvertently or not, the app had played on racist stereotypes; and it might have reduced local businesses’ profits or poured fuel on the fire of gentrification. The concept of sketchiness is inseparable from prejudice: if American cities were not riven by inequality and fear, there would have been no market for SketchFactor. In light of all this, it seemed that the best way for McGuire to fail up would be to acknowledge some culpability, and to promise that Walc would do better.
“Is there anything you regret?” I asked.
“I regret that we were misinterpreted by the media,” she said. “I lost twenty pounds in two weeks.”
McGuire, who received unwelcome attention from Internet trolls, has reasons to feel aggrieved. Still, I was surprised at how she was choosing to frame her story. In the recent book “So You’ve Been Publicly Shamed,” the journalist Jon Ronson meets several people who have been brought low by online hordes. Some of them are indignant; others are self-lacerating. All of them, with one exception, offer some sort of apology. (The exception, a man who was accused of hosting a Nazi-themed sex orgy, is so unflappable, so anomalous in his inability to feel shame, that it becomes one of the book’s central mysteries.) Not all of the apologies are good ones. The one offered by the monologist Mike Daisey, whose work conflated truth and fiction, is particularly evasive. But even Daisey, at one point, manages to spit out the words “I’m sorry.”
This was the first interview McGuire had granted in months. Setting it up had required weeks of negotiation. She had clearly spent time and money crafting a media plan; yet that plan did not seem to include a one-sentence apology, even a qualified one of the “I’m sorry you got upset” variety. Perhaps she had been advised to project unalloyed confidence. This seemed, at the very least, like a bad tactical decision.
Many tech founders appear to inhabit a world without accountability—if not above the law, then above the social convention of occasionally eating crow. For all their talk of failed elevator pitches and failed redesigns and failed companies, they are loath to talk about interpersonal or moral failures, which are both more embarrassing and more important. As one entrepreneur, explicitly channelling the spirit of Steve Jobs, wrote on Medium, “Dive in. Do. Stop over-thinking it.” In this world, there are no bad ideas, only bad market fits.
In life, if not in business, not all ideas are good. Some cause real harm. Talking about race can be uncomfortable, and white people, who have the luxury to opt out of such conversations, often do so. It’s unpleasant to admit that you’ve made a mistake, and it takes work to do better in the future. It would be dangerous if the tech élite got into the habit of dismissing such work as weakness, or as a waste of time.
For the rest of our interview, we talked about Walc. McGuire said, “Google Maps makes you figure out where you are by looking at a blue dot and turning around and around—we call this the smartphone pirouette—until you figure out which way the arrow is facing. Our innovation is to give you landmark-based directions: walk away from the Chase Bank, toward the McDonald’s. We plan to do integration with those businesses, consumer deals that pop up seamlessly as you pass storefronts. We want to be a friend in your pocket. There are some shortcuts that every New Yorker knows: You don’t have to walk around the block—you can just cut through the playground. That’s the kind of thing that can help you walk smart.”
“So let’s say it’s midnight,” I said. “You want to walk from the Upper East Side to the Upper West Side. Clearly, the quickest route is through Central Park. But many New Yorkers would say that’s unsafe. Would your app take that sort of thing into account?”
“Right now, we’re not focussed on that,” she said.
