It's 2 a.m. and Dennis Crowley is wired.
We've just left Foursquare's South by Southwest party at the Hype Hotel, a warehouse-size space in downtown Austin where nearly 1,000 revelers were drowning in deafening club music and Tito's Handmade Vodka. Crowley, 36 at the time in March, played host, quadruple-fisting Miller Lites and hanging out with his startup's leadership team, including design director Ian Spalter, then also 36, who wore earplugs and a hoodie tied around his waist. "I'm getting too old for this!" Spalter yelled over the bedlam.
Outside on the sidewalk, streams of partygoers hail pedicabs and stumble home as the night comes to an end. Crowley isn't ready to call it quits just yet. He's leaning against a nondescript door, flanked by a small crowd of twentysomethings. Turning his head like a secret agent checking his six, Crowley flashes his trademark puckish grin. "You're coming to the after-party, right?" he whispers. "Just play it cool." The door suddenly pops open, and Crowley exchanges a few hushed words through the crack. Then the group races inside and up six flights of stairs as if a pot of gold awaited them at the top. (In reality: more bottles of Tito's.)
That Crowley still commands such a following at the Austin tech conference is a testament to his willpower. It's not just Foursquare's fifth annual SXSW appearance but Crowley's eighth—a point at which he might feel like the high school football star still grasping at the glory years. Crowley debuted his location-based service here in 2009 to much fanfare. The app lets users "check in" to venues via smartphone and share their whereabouts with friends—a tool perfectly designed for discovering hot bars and parties during the weeklong festival. Foursquare's launch heralded the idea that broadcasting our location could unlock invaluable information—not only for users searching for a nearby coffee shop but also for merchants looking to entice them with instant deals and rewards. The press hailed Foursquare as the next Twitter, which also had blown up at SXSW, in 2007, and soon Crowley's New York-based startup was rocketing toward superstardom.
That path has taken longer than expected. "If you know where everybody is, where they're going, and what they're going to do when they get there, and you can't make money on that, you're a fucking idiot," says notable web entrepreneur Anil Dash. He first expresses that sentiment to Crowley during their SXSW keynote interview this March, and delivers it as a joke. When he repeats it to me a few months later, it begins to sound like the truth. That's because after 4 billion check-ins, plus 35 million users and partnerships with brands such as American Express, Foursquare can't seem to fulfill its promise. It reportedly pulled in a paltry $2 million of revenue last year, and user growth has slowed. There's been some measure of internal dissension, peaking when cofounder Naveen Selvadurai abruptly left the company in March 2012.
Crowley is now a lightning rod, making news (or what passes for it in the tech scene) for tweets or public appearances. He spent much of this year's SXSW dogged by rumors that Foursquare was bleeding cash and struggling to raise additional funds. Yelp board member Keith Rabois has been Foursquare's most vocal detractor, calling its potential a "myth" and suggesting the company's only hope is a Hail Mary acquisition. Crowley has spent more than a decade pursuing his dream of building the world's social GPS. (Foursquare is his second startup to chase the idea; he sold his first, Dodgeball, to Google, but the search giant let the product wither.) Some now wonder if Foursquare's true Achilles' heel might be that Crowley's bet, his life's work, has been flawed from the start: Maybe users simply don't like sharing their location the same way they love sharing a photo or a status update.
But Crowley has never been more convinced of his mission—or more pugnacious in responding to critics. "Over the last couple of years, we've had to build a lot of stuff just to fight for survival, so we don't get crushed by a Facebook or Google," he says. "It's been like working our way through [video game] Mike Tyson's Punch-Out." Since securing $41 million in debt financing in April, Foursquare has reinvented itself as a local search and discovery engine, distancing itself from the check-ins and virtual badges it had become known for. It's finally opening up its advertising tools to the 1.4 million merchants already using the platform. And its location data are powering a slew of services such as Uber and Path, making Foursquare a dangerous competitor to the $2.2 billion Yelp (and perhaps explaining why Rabois, who declined an offer to comment for this story, has been so rabid in his attacks).
"We're now at this point where it's really hard for us to go away," Crowley says. "People will say, 'Oh, you're not killing it like Google.' Well, Google's got 50,000 people. 'You guys aren't as profitable as Facebook.' Yeah, well, they have 4,900 people and have been around for 10 years. We're [four-and-a-half] years old with 160 people: Give us a chance to grow into what we are."
Crowley isn't blind to the challenges. He's a constant self-evaluator; his scale even tweets out his weight once a week (holding steady at 165 pounds!). Foursquare has brought him a long way, further than most startup founders ever get to go. But he knows that somewhere, somehow, this leg of the journey has to end.
If you didn't know him, you might think Crowley was experiencing an early midlife crisis. The chief executive just got his motorcycle license. Vintage snowboards line the walls of his East Village apartment. At a wedding not long ago, one friend remembers a tuxedoed Crowley sliding on his knees under the legs of his dance partner. Chalk it up to a boyish earnestness—a contagious enthusiasm that drives him to sing karaoke with coworkers into the morning hours (his poison: Guns N' Roses singles) or to organize all-day PlayStation 3 tournaments on the weekends, to the frustration of his fiancee, fashion stylist Chelsa Skees. "Dennis never stops," says Christian Bovine, a close friend. "His classic line is 'Let's just do one more.' No matter how late it is—even if we've already done six one-mores—he'll be like, 'We can do one more.'"
Though Crowley is often the life of the party, his true social grace is his underlying humility. He loves dive bars, complains about pricey food, and it drives him "fucking nuts" when people treat him differently because of his high-profile gig. (At a recent tech gathering in Brooklyn, a wide-eyed attendee didn't recognize Crowley and asked what he did. "I work at a tech startup," he replied.) Crowley contends the high visibility of running one of tech's most-watched startups—a life that comes complete with ads for Gap and Best Buy and Annie Leibovitz photo shoots—hasn't changed him. Unlike many of his startup-CEO contemporaries, he's been hardened by years of failure and once had to survive on unemployment checks. Says Crowley, "You get knocked down, get back up, and just start building again from scratch."
Crowley grew up in Medway, Massachusetts, a middle-class suburb of Boston; his father owned an electrical contracting company and was nicknamed "Big Dig" for his work on the interminable construction project. Crowley didn't focus much on getting good grades but fondly remembers using his dial-up modem to find subscribers online for Dystopia, a fanzine he created in high school to cover everything from The Legend of Zelda to skateboarding.
At Syracuse in the mid-1990s, Crowley didn't have the prerequisites to take computer science courses, but he was happy enough having a high-speed Internet connection and scanner to share photos. ("That was my jam!" Crowley beams, trotting out his oft-dated lingo.) He learned Photoshop to create flyers for the parties he threw, at one time raking in four figures overnight for a particular rager. He blogged about his antics before blogging was hip and even set up a webcam to broadcast his dorm-room drinking games—a then-novel idea that landed him in Wired. After graduation, he worked at the tech firm Jupiter Research, and then Vindigo, a pioneering city-search service for PalmPilots. Online city guides were huge at the time, but Crowley found them boring. They never seemed to know about the cool places he and his friends were going. "I was like, This is so broken. Fuck it, I'm going to build my own," Crowley recalls. He taught himself to code and developed the project on dodgeball.com. (He tried to purchase foursquare.com back then, but it was unavailable.)
"Dodgeball was so closely a distilled version of what fascinates Dennis," says Curbed founder Lockhart Steele, an early user. "His passion is discovering new things, like the hot dog with weird toppings, or that bar with the secret trap door."
Soon, however, the dotcom bubble burst, and Crowley was laid off from Vindigo and forced to move. "I went from feeling like the shit with my high-paying job to getting laid off, evicted, and dumped by my girlfriend," Crowley says. "It was like, Fuck, I'm 25, and I'm moving back in with my mom and dad?" He instead retreated to New Hampshire, where he became a snowboard instructor making $6 an hour.
He applied to grad school and in 2002 was accepted to New York University's ITP program, where he met Alex Rainert. The two soon dusted off Crowley's Dodgeball ideas for their thesis project. They built a text-based service that enabled location sharing: Text "@AceBar" on your cell phone, and Dodgeball would bounce a notification to your friends. It gained a cult following among their crew, who loved using the social tool to meet for drinks in downtown Manhattan, and it "quickly went from 5 to 10 to 22 cities," Rainert says.
A chance encounter turned Crowley's life upside down again. On a 2004 trip to San Francisco, he planned to crash on his friend danah boyd's couch. But boyd, then an intern at Google, couldn't pick him up from the airport while she was at work, and Crowley couldn't afford the taxi. "I concocted this ridiculously stupid plot to get Dennis invited to Google, to basically justify his cab fare," boyd recalls. Her boss, future Twitter cofounder Ev Williams, approved, and Crowley was soon in Mountain View, California, giving an off-the-cuff talk on the future of mobile, which caught the attention of Google's team. By May 2005, Google acquired Dodgeball for an undisclosed sum. ("It wasn't set-for-life money," Crowley stresses.)
Crowley had high hopes for Dodgeball at Google yet remembers few who appreciated social's benefit to search. "I would be like, 'Show me all of the places where my friends go on Saturdays around noon in the East Village,' to see the most popular brunch places," Crowley says. The search giant devoted few resources to Dodgeball, and Crowley quit in less than two years. "It was like watching a kid's science-fair project get squashed," recalls Crowley's friend Will McDonough. "I remember wondering, God, does he just get a regular job now?"
Crowley ended up at a startup called Area/Code; he spent most weekends snowboarding, hooking up clunky GPS equipment to his body so he could track his location as he bombed down the slopes. "I was in a really shitty place—depressed for nine months," he tells me over dinner and a half-dozen bourbons at Lafayette, a trendy Noho restaurant that Crowley arrived at wearing running shoes and a track jacket.
The only saving grace came from meeting Naveen Selvadurai, who worked in the same office. Selvadurai was also obsessed with location tools. He worked at a startup that tagged digital "sticky notes and stories" to locations, and in his spare time created a browser bookmarking service for his favorite spots in the city. The two started hacking projects together. Recollections vary, but Crowley points to a friend's birthday party in January 2009 as a turning point. During the gathering, news broke that Google was shutting down Dodgeball. "Everyone was freaking out," Steele recalls.
"I have this vivid snapshot in my mind of standing at the bar, and the news traveling back and hitting me like a rock-hard weight," Crowley says. "They're going to turn Dodgeball off? Naveen and I were like, 'Let's stop dicking around and build another one.'"
Two months later, Crowley and Selvadurai introduced Foursquare at SXSW, where it stole the show.
In late 2009, Crowley arrived at Tres bar in San Francisco to meet Tristan Walker, one of his first hires. Minutes after Crowley checked in on Foursquare, a group of two dozen people surrounded their small table, and Crowley soon led them to a brewery down the street. "He was like the Pied Piper," says Walker. But to him, it wasn't just a sign of Foursquare's increasing popularity and Crowley's growing celebrity. "At that moment, I also realized Dennis was the embodiment of his own product."
Startups are always tied to their founders; rarely has the identification been so close as Foursquare is with Crowley. It has worked in his favor during the beginning of the hype cycle—a process every hot startup goes through—from the magazine covers Crowley was featured on after Foursquare surpassed a million users to the television coverage he received for raising a $50 million round from Andreessen Horowitz and Union Square Ventures. But even as Foursquare topped 15 million users and 500,000 businesses in late 2011—with brands like Starbucks flocking to the service—the polish was already starting to wear. The struggles of the past year in particular have turned into not just a referendum on Foursquare's potential but on Crowley's tenure as CEO. "It's inevitable with such high expectations that everyone will turn on you," says Foursquare employee No. 4 Nathan Folkman, now the CTO of Path, which is experiencing its own honeymoon period. "People are in love with you, but then all of a sudden, they can't wait to watch you fail."
Digging out of the pessimistic muck isn't impossible, but Crowley's mistakes have made his job more difficult. Foursquare is a more evolved Dodgeball, offering features such as badges and rewards to incentivize engagement—check in to four different bars in one night, say, to earn the "Crunked" badge. But the app got stuck with the perception that it's nothing more than a juvenile game. "We didn't want to be known as the badge company—that could have gone horribly wrong," Crowley says, although that's arguably what happened.
Foursquare also has struggled to connect with advertisers: It had no local sales team and uninspired merchant tools, and its money-generating search ads saw little traction when they were introduced. Multiple sources confirm that Facebook and Yahoo attempted to acquire Foursquare early on for around $100 million, but Crowley and Selvadurai declined and the offers dried up. Meanwhile, the similarly minded local search company Yelp went public, and its stock soared 64% on its first day of trading in early 2012.
Those close to Crowley say the stumbles forced him to mature. "I've watched him grow from this giant boy into a man," says chef Sarah Simmons, who has known Crowley since the early aughts. "We're not just children anymore having a good time." Crowley, who once thought he'd never need more than 20 employees, had to revise his long-held vision for what Foursquare should be. He even sought CEO coaching. Danah boyd calls it the "canonical story" of a startup. "Like, 'I'm no longer building an excuse for my friends to get together to drink beer; I'm now accountable for building a sustainable business,'" she explains. "He had to make really hard decisions about the company's direction; about new rounds of investment and the possibility of an exit; about management issues that were really uncomfortable. That weighed on him—big time."
The most significant test for Crowley came in March 2012, when he split from his cofounder. They had once shared duties, but as the company made more hires, Selvadurai was lost between roles, and it appears Crowley decided to go solo. "Naveen got pushed out and it sucked," one source close to both parties says. "But it was a turning point for Dennis as a leader—it was probably the hardest thing he's ever had to do." The event wasn't publicly discussed, and Crowley will only say Selvadurai's departure was "part of the company maturing." The tech press saw the episode as a sign of the company's brewing internal struggles, and thus started what Crowley calls the company's "hazing period." Headlines parroted Foursquare's funding and revenue woes. PrivCo, a research firm focused on private companies, said Foursquare was in a "death spiral" and would go out of business.
This summer, over dinner at a restaurant only 400 feet from Foursquare's headquarters, Selvadurai had his first on-the-record conversation about the exit. He's still visibly hurt by it, like a man not yet over his divorce, and yet spoke politely, if hesitantly. "It was definitely a surprise. I wanted to stay," Selvadurai says. He'd look away and take long pauses, trying to find the words. He wouldn't go into detail. "This was my baby. To leave everything behind—it was the worst kind of breakup ever. I truly feel like an orphan." Though he remains a shareholder, Selvadurai left the board in October. When asked if he's on good terms with Crowley, Selvadurai only says, "We haven't talked in a long time, since that last conversation."
For the rest of 2012, Crowley set about transforming Foursquare, deemphasizing check-ins and highlighting its tools and information to search for and discover great places. The company completely overhauled its user interface, bringing its search engine to the forefront so that new burger joints or taco trucks are only a tap away. Search usage doubled in two months. Its venue web listings received their first refresh since 2011—a smart shift to recapture forgotten users—and now 50 million monthly visitors scour Foursquare's expansive library of reviews. The company also seamlessly integrated Visa and MasterCard to offer merchant discounts, and the app now comes preloaded on a string of smartphones. "It doesn't bother me that other people can't see what we're doing, because they couldn't see it when I was in grad school, and they couldn't see it at Dodgeball," Crowley says. He now has numbers to help him tell his story: Every metric the company tracks—active users, sign-ups, check-ins—is up at least 10% to 30%.
By April 2013, the company raised $41 million in convertible debt. The savvy move by Crowley bought his company more time while halting talk of Foursquare's demise. His pitch to investors now is about opportunity: "There's no doubt in my mind that what we're building will be used by hundreds of millions of people," Crowley tells them. "The question is: Does it have the Foursquare logo on it or does it have another logo on it, because someone beat us to it?"
One chilly night in early June, Crowley texts me: "In SF, want to hit a sushi bar?" He arrives at Ryoko's, his go-to spot, wearing a New York Cosmos hat (Pele's old soccer team) pulled low like a celebrity hiding from the paparazzi, with his Justin Bieber-style mop of hair exploding from all sides. We grab two seats at the bar and go "splitty-split" over tall bottles of Kirin and fat cuts of sashimi. Crowley is in town visiting Foursquare's San Francisco office, but he also wants to show me the company's future.
As a tray of juicy Kurobuta sausage arrives, Crowley dives into the next iteration of the app. He tends to slouch his head when talking, sporadically making eye contact to be sure I'm still with him—more often as he gets excited and begins talking faster. He walks me through not just "Panda Time," the code name for the latest internal build of Foursquare, but also an even more secretive version of the product, which at the time only five employees have seen. The gist is that Foursquare no longer requires you to tell it where you are; the app is now smart enough to sense your location and offer recommendations for what to do while you're there or after you leave. "I want the next Foursquare employee who comes in here to get a message that says, 'Dennis was here two weeks ago—whatever you do, get the sausage,' without having to open the app," Crowley says, locking me into his gaze.
It's a compelling prospect: If Google has built a $294 billion business based on your explicit searches, Foursquare's bet is that the data behind your implicit intent are just as lucrative.
Foursquare introduced a similar feature in 2011 called Radar, but it was plagued with problems. Not only was 24/7 GPS a serious battery drain, but Foursquare didn't have enough interesting content to deliver. Now, with billions of check-ins and 33 million user-generated tips (which is creeping up on Yelp's 42 million reviews), Crowley says Foursquare has evolved to the point where it knows whether we'll want to head to a cocktail bar or get dessert after dinner. Engineers have been working for about eight months to calculate when to fire up your smartphone's sensors—its gyroscope, accelerometer, GPS—to determine what you're doing while keeping energy use low. "We can tell when it's warm out; that you've been to ice cream shops in the past; that it's the middle of the afternoon; and that you just left the office because your phone is moving," says Crowley, who can be a dynamo salesman, his hands moving faster than the sushi chef slicing fish behind the bar. "That's an opportunity to serve an ad like, 'You gotta come have one of our milkshakes.' We should let merchants compete for your business."
Crowley stresses that the product is still in development—he planned to introduce it to the entire Foursquare team that week for internal testing. After Crowley's iPhone had been resting on the bar long enough during our dinner—about 10 minutes—Foursquare buzzes the device, guessing with 30% confidence that we're at Ryoko's. The question now is what content to show and when. "It's at that Frankenstein moment: 'It's alive!'" Crowley says.
That's not to say explicit search and check-ins are going away. They still remain Foursquare's bread and butter, and the company is currently testing myriad advertising products. In April, Gawker published an internal Foursquare document revealing some of these tools, such as banner ads that would pop up after checking in, taking advantage of your location to target such demographics as the "mass-market mom." Check in to a Lower East Side nightclub, for example, and Foursquare might trigger an ad for Stolichnaya vodka. Crowley confirms the company is experimenting with the essence of that idea. "If you check in at Walgreens, should we show you an ad for toothpaste? We're not sure," he says. "Does that dilute the experience?"
The biggest near-term revenue will likely come from the 1.4 million local merchants on the platform. The company plans to start charging them for its ad products on a cost-per-action basis later this year, which could prove a boon to its bottom line. "Maybe you're slow during the day, so when people search for a lunch spot, you run an ad in the neighborhood for your rotisserie chicken salad. Say we showed the ad a hundred times and six people showed up within the next three hours—that's a pretty good conversation rate," Crowley says. "So maybe we pick up $200 per month from that venue. Take that from 10% to 20% of our million venues, and that's $20 million to $40 million a year."
Crowley's math isn't outside the realm of possibility. Later that month, when I press Foursquare investor Ben Horowitz about the startup's meager $2 million haul in 2012, he tells me the company has already exceeded last year's revenue by roughly four times. A back-of-the-envelope calculation indicates Foursquare is thus on track to take in around $15 million to $20 million in 2013—and the revenue growth could speed up as the company begins to charge more merchants and roll out more ad products.
That turnover still pales in comparison to Yelp, which saw $46.1 million in net revenue in the first quarter of this year alone. But Foursquare's location data is proving an increasingly hot commodity and now powers products including Facebook's Instagram, Twitter's Vine, and Yahoo's Flickr. (Right now there's no money involved; Crowley is just sharing with these services, because their users help Foursquare learn which businesses are popular—and when.) Reports surfaced recently that Apple senior vice president Eddy Cue was in preliminary talks for a data-sharing deal to help its troubled mapping service, and Facebook and Google went to battle this spring to acquire Waze, the social-mapping startup, which Google managed to snap up for $1.1 billion.
The changing landscape offers vindication for Crowley. "People are always like, 'We're rooting for you! You've been at this for so long!'" he says. "I've never liked that attitude. We're finally close to showing them like, 'Whoa, this isn't a toy. This is something that's going to change the way we interact with the real world.'"
Crowley says he rarely feels old, but his bones ache more now after snowboarding. His younger siblings are married, and his kid brother has a baby girl. Yet he is frozen in a moment many startup founders experience in their twenties: the big push. "This job is exhausting," Crowley says. "My buddies are like, 'You live the most amazing life!' Well, I'm working like a dog. I come home most nights and pass out on the couch."
Crowley says it's been "super-stressful" on his relationship, too, but Skees, his fiancee, knows this life. They've been together since shortly before Foursquare's founding, and friends describe her as his rock—one that has tamed his out-all-night lifestyle while still supporting his dreams. They're currently planning their October wedding. A friend recently told Crowley that if he could go back in time, he wouldn't have put off having kids to do a startup. And Crowley is well aware of what's become of him: His identity is his company; he is only as mature as it is. "I've thought about it for a while, and to me it's like I've got to close this chapter in my life before I can go on to the next one," Crowley admits over beers in Cobble Hill, Brooklyn, one Saturday afternoon, as parents stroll by with baby carriages. Earlier that day, we bumped into Alex Rainert, Foursquare's current head of product (and his Dodgeball cofounder), who was taking his daughter to ballet. "It's like arrested development—when you're stuck in the same place where you were at 26," Crowley continues. "My mind-set is of the person who is still unsure whether they have enough money in their ATM to go to another bar. I lived that way when I was unemployed, when I was a snowboard instructor, and when I was at NYU. A lot of my personality is stuck in those five years, and I don't know if that's ever gonna change."
Perhaps it's the cruel burden of near-success—like a Triple-A baseball player, losing his youth waiting for a call-up from the majors but unable to quit because he's so close. The Jack Dorseys and Kevin Systroms and David Karps were all here, and then a step further. Crowley insists he didn't get into business to make money. And he claims—perhaps not that believably—that it doesn't matter to him whether he's a "mid-level PM [product manager] somewhere or the CEO of an independent company." But no matter what, he does intend to keep shaping Foursquare—or at least the idea it's premised on. That's what he believes in the most.
Anil Dash says he's seen this before: Crowley is a rare breed of founder obsessed with the problem he's trying to solve. "The thing I fear, which would be devastating for the industry, let alone Dennis, is that he gets rushed and Foursquare can't monetize, they can't raise [another round], and they have to sell to Facebook or Google or whoever," Dash says. "And then at 40, Dennis has to start over. Because he'll do it again—there's no question. But then the world will have to wait another goddamn 10 years for this thing."
And so every next step is important; the service must evolve so that Crowley can as well. At a product meeting earlier this year, the Foursquare team gathered to discuss its new "ghosting" feature. In the old version of the app, a check-in stayed visible until a user checked in somewhere else; if you went to Starbucks at 10 a.m. and didn't check in anywhere else all day, the service believed you were having a really long coffee break. Now those marks would fade away if they stayed too long in one place: The older they are, the less useful—and therefore less visible—they become. Crowley sat in on this meeting looking confused. He was squinting at a map of the neighborhood they were in, but his last check-in wasn't on it anymore. "I don't see any ghosts," he said.
"You won't be ghosted," a product manager explained to him. "You'll just be gone."
Crowley thought this over for a moment. It made sense, so he approved.
[Photographs by Gus Powell; Axel Dupeux (Spalter)]
A version of this article appeared in the September 2013 issue of Fast Company magazine.