Few people could turn that mentality into a $600 million business. But he did.
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.
Crowley and his roommates pose with $1,600 and a police ticket the earned from one party.
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.”
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.