Photo: tantek via Flickr
For Dennis Crowley, life has always been a game that should be played with friends. Few people could turn that mentality into a $600 million business.Dennis Crowley sold his first startup to Google. His second, Foursquare, has nearly 100 employees, 16 million users, and it is creeping towards a billion-dollar valuation.
Crowley is the poster child for New York’s burgeoning tech scene, but his success didn’t happen overnight.
It was a series of failures and disappointments.
Crowley chronicled the experience on a personal blog, Teendrama. We’ve read through that archive and spoken to Crowley, his family and his friends to learn how the party-prone teenager became one of the youngest, most successful entrepreneurs in the world.
* * *
Crowley grew up in a close-knit family that made everything playful. When they were in church, they’d create competitions to see how many hands each could shake during Peace Be With You.
“We’d flash the number to each other and be like ‘Oh I got 6!’ The family record is 15 or something,” says Crowley.
It wasn’t long before these kinds of social games turned into a social business.As an upperclassman at Syracuse University, Crowley and his friends threw parties for freshmen. Freshmen were unable to get into bars and they were desperate for alcohol. Crowley charged a cover at the door. One party alone made him $1,600.
“We made so much cash and eventually got busted by the cops,” Crowley, then a Junior at Syracuse, wrote. “I ended up having to go to court with Kevin – we were charged with a simple noise disturbance violation and paid nothing. Aw-yeah.”
VIDEO: Crowley's “Getting Hammered Cam” – the first-ever webcast of a drinking game. Pause at 0:03 for a full moon.
Crowley found technology could make social situations better.
He kept a diary online as a teenager. Called Teendrama, it's where we learned about Crowley's early life before sitting down with him for an extensive interview.
The tech-savvy teen was also one of the first Syracuse students to wire a dorm room with Ethernet.
Crowley set up a "Getting Hammered Cam" that transmitted live videos to a video conferencing server at Cornell University. On it, he and his friends recorded and preserved memories of otherwise fuzzy nights.
Despite his aptitude for partying, Crowley had all the makings of a successful entrepreneur. He had an up-for-anything attitude and a sense of humor that promised no moment would be dull. He could corral people and convince them that any idea he conceived — whether it was running with bulls in Europe or seeing how high you could throw a bowling ball in an alley — seem good. He could work his way out of impossible situations and he was resourceful.
Take, for example, the time Crowley almost didn’t graduate.
In June 1998, Crowley received a phone call from Syracuse University. All of a sudden Crowley found himself five credits shy of a diploma.
“It turns out that someone in the recorder's office made a mathematical mistake last semester (a two credit mathematical mistake) that made my transcript seem like I was right on track when I was really a class behind,” Crowley wrote on Teendrama.
"Whose fault? They say me, I say them.”
Crowley convinced the school to let him blog for the remaining credits. Teendrama, where Crowley was already writing about his college antics, became his independent study. Crowley received his degree in January of 1999.
Around this time, Crowley created another personal Web page that would be home to new projects. It was called Dodgeball.com.
* * *
Upon graduation, Crowley moved to Manhattan to work for Ken Allard as a research associate at Jupiter Communications.
Allard says Crowley had a "quiet leadership quality."
"People flocked to Dennis. He wasn’t up in the front of the room saying, ‘Hey, follow me.’ He just did stuff that was fun and people wanted to be with him. He’s always been that way, and that has never changed.”
Even among a staff of 200-300 people, Jupiter founder Gene DeRose could see Crowley shine. “Dennis was absolutely one of a couple that everyone kind of knew they had to keep an eye on,” says DeRose. “You weren't sure if it was because he was always at the center of a social hoard of people or whether it was because this was an entrepreneur. The irony is that, in the end, there kind of was no difference.”
When DeRose heard Crowley might leave Jupiter for a mobile company called Vindigo, he personally took Crowley to lunch. Crowley left anyway.
At that moment, Crowley was on top of the world. He wouldn’t remain there for long.
“I remember thinking, what a cool life this guy lives,” says Jonathan (J) Crowley of his brother. “He was working at a hot tech company, going out all the time, he had lots of friends … and then it all disappeared.”In 2001, the week Crowley turned 25, Vindigo went through a series of layoffs and Crowley was let go. That same week he was evicted from his apartment.
Crowley spent the summer trying to line up interviews, but jobs were scarce.
Then, one September morning, Crowley woke up to a crash.
He wrote about it on his blog.
“I got up, grabbed some juice, turned on my laptop to find a bunch of IMs from people telling me the WTC was bombed. I turned on the tv then ran upstairs to check out the scene from the roof ... The hole on the South Tower (left side) has to be at least 20 stories high.
"I spent the next 15 minutes on the roof waiting for the dust clouds from the first tower to clear. I was up there when I heard the second boom and watched the North Tower crash to the ground.”
On September 11, Crowley watched the twin towers crumble before his eyes.
Crowley's life, it seemed, followed suit.
In a matter of months he lost his job, his girlfriend, his home, his direction and eventually New York City and all the friends it held. Crowley was forced to move home to New Hampshire. He hadn’t a clue where life would take him next.
Crowley remained in New Hampshire for the next seven months. It was a tough transition and his spirits were down.
“He went from living in New York to living in a tiny little ski house in New Hampshire, and from making a good amount of money to making about $6 per hour teaching kids to snowboard,” says J.
Dodgeball had continued to transform as Crowley’s side project, but up in New Hampshire he didn’t have the heart to work on it.
Bored, alone and broke, Crowley survived by making a few ground rules. From his blog:
Note to fellow unemployed kids: (aka Rules to Live By)
1. Leave your apt before noon every day.
2. No drinking before 5pm.
3. No watching TV before 5pm (except during lunch).
4. No taking taxis.
5. No eating meals when drunk.
Resilient, Crowley turned the bad times into jokes and wrote haikus for his troubles:
you never showed up this week.
please come again soon.
every month i throw
eighty dollars towards this gym.
towels should be free.
i already know i'm poor
keep your damn receipt
hello girl from nerve
i wish you were half as cute
as you looked online
99 cent nugs,
junior bacon cheeseburger
and a frosty, please.
send a card - or just "forget"?
my heart she broke. twice.
Finally Crowley applied to graduate school; Allard wrote his recommendations.
Crowley was accepted into NYU's ITP program. He packed up his bags and moved back to Manhattan where he met fellow student Alex Rainert.Rainert and Crowley met at orientation where a few students were gathered around a video game.
"Looking back it's funny," says Rainert. "A lot of elements of the video games we discussed ended up being implemented in Dodgeball and Foursquare."
With their shared interests in gaming, mobile, social, music and sports, the two became fast friends; Crowley would later be in Rainert's wedding. Throughout graduate school Rainert and Crowley worked on side projects like Dodgeball together.
By then Dodgeball had morphed into a crowdsourced alternative for the slow-to-update site, CitySearch.
Crowley introduced the game to other NYU students and worked with a professor, Clay Shirkey, to develop it during an independent study. Rainert and Crowley refer to Shirkey as the Patron Saint of Social Media. With his help they tested out social and mobile features for Dodgeball, like Shouting, where messages were sent within a 15 block radius.
Users would "check-in" to bars or restaurants by sending a text, and all of their "friends" on the service would get a text with the location. Users would get points for checking in.
It wasn’t until graduation in May 2004 that Rainert and Crowley considered forming a company around Dodgeball.
Rainert and Crowley were both interviewing for other jobs at RGA and MTV respectively. At the same time Dodgeball gained traction; a half-page article was written about it in The New York Times. “We thought, ‘Maybe this is supposed to be our jobs,’" says Crowley.
The pair gave themselves six months to turn Dodgeball into a business. That summer Crowley learned about finance and angel investing. Their pursuit of capital led them to Google’s doors in September.
Google was fresh out of its IPO and it wasn't in the habit of investing in startups. When Crowley and Rainert met with Google they were told, according to Dennis, "We don't really finance companies but maybe you guys should just come and work here."
That moment was one of the high points in Crowley’s career.
He wrote about it on his blog, of course.
“Hey kids, my grad school thesis project (and what seems like my life's work), dodgeball.com, was acquired by Google today!
“Special shoutouts to everyone that's helped out. Tallboys for everyone. Forever!”
But the high didn’t last, and selling to Google ultimately put Crowley at another low point.
* * *
Within a year and a half, Crowley and Rainert realized they weren't a fit at Google. Instead of helping Dodgeball grow, Google stifled it.
“I know what it was like when he left Google and that was a really hard time for him,” says J. “Everyone sees this side of Dennis that's so electric but there was a phase when he was in a rut. He was in a tough position. I don't think he could find the energy to get himself excited.”
Crowley says, “It was like, ‘Oh my god we sold a company to Google!’ And then, 'Oh gosh, it didn't work out, now what am I going to do?’ You can't get a job because no one wants to hire the failed startup founder. You don't know what to do."
After Google, Crowley found work at a company called Area/Code. Rainert found a gig too.
The pair now call those jobs "rebounds," but they were pivotal learning experiences for their future company, Foursquare.
In his new role, Rainert learned to grow and manage a product team. At Crowley's, he worked on games and met Naveen Selvadurai.
Selvadurai had a desk around the corner from Crowley.
“He was the one guy who knew how to make iPhone stuff. He liked hacking city apps,” recalls Crowley. “I was doing a lot of mobile work and I also liked city stuff and we just started working together. We were experimenting for four to five months. It wasn't until January 2009 when we said, ‘Let's get serious about this and launch it for SXSW.’”
At this point, Apple's App Store had been around for almost a year. The popularity of the device created a whole new market for what Crowley wanted to create with Dodgeball.
Crowley was inspired again. Technology had caught up with his life-long vision.
WATCH: Dennis Crowley on how he sold his company to Google, how Foursquare came about and his plans for the future (Interview with Henry Blodget from BI’s Startup conference, May 2010.)
The ordinarily social Crowley became reclusive.
“When Dennis stops socializing, you know he’s working on something really big,” says J.
One week in January, a rare event occurred: A Friday and Saturday night passed with no sign of Crowley.
An entire week passed and J still hadn’t heard from his brother.
“Then a group of us got an email that said, ‘Hey guys, I built this, what do you think?’ It was the first version of Foursquare; it was originally called Jimmy Disco,” says J.
Today, Foursquare has 100 employees, more than 15 million users, and a valuation of $600 million.
But Foursquare wasn’t always smooth sailing for Crowley.
“Everyone thinks the Foursquare experience is this rocket ship that started at SXSW 2009 and it hasn’t let up, when in reality it was a little spike and then a summer of nothing,” says Crowley.
It took him and Selvadurai about nine months to raise the first round of capital for Foursquare.
“Then it spiked back up and it plateaued, and it spiked back up and it plateaued,” he says. “Of course if you average it out [the Foursquare experience] looks like a nice hockey stick curve. If you zoom in a little bit it is super, super rocky.”
The rollercoaster that is Foursquare is a good analogy for Crowley’s life.
“My whole career is a bunch of sizzles and spikes,” says Crowley. “I’m still trying to make sense of all of it, but when you look back it all starts to connect. Everything connects in hindsight. Of course you don’t realise any of that going forward, you only realise that when you look back.”
In many ways, Crowley is still the same shaggy-haired socializer he was in college. He still looks to make every situation more fun — last month he traveled across the country with five ridiculous-looking corn cob pipes to surprise his friends in Lake Tahoe.
“I hope he stays the way he is and doesn’t grow up,” says J. “He’s about to turn 36 but Dennis hasn’t slowed down to me. He is somehow able to keep that energy.”
J’s favourite moment with his brother? Winning Family Feud.
As a business person, Crowley has grown up quite a bit. Foursquare has had opportunities to get acquired, but Crowley wants to keep control of his company this time around.
He has learned to strike a balance between fun and business although the two often overlap.
Crowley says he can be “a little bit of a hard-arse;” pushing people to create better experiences than they thought possible.
For Crowley, the quest to make life one big, social game may never be complete.
“Someone introduced me the other day as a serial entrepreneur and I don’t see it that way at all,” he says.
“I’ve been trying to solve the same problems for many years and build software that helps optimise downtime. Of course the problem set keeps evolving and changing.”
Perhaps Crowley’s life-long wrestle with Foursquare stems from the fact that he so deeply embodies the product. Life, for him, is a constant game of checking in with people he loves. The personal reward he gets from being with friends and discovering new ways to have fun is what he wants every Foursquare user to experience.
At one point in our long interview, Crowley said: “I don’t socialize more than the average person — maybe I do maybe I don’t.”
Told he almost certainly does, Crowley smiled and asked: “What do people normally do after work?
“Do people just go home? I feel like there’s almost wasted time when you’re not enjoying things with friends.”
For more on Crowley’s life don’t miss: IN PICTURES: The Life And Awesomeness Of Dennis Crowley, founder of $600 Million Foursquare
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