The Entrepreneur Lifestyle

English: Dennis Crowley in Foursquare's New Yo...
English: Dennis Crowley in Foursquare's New York office, USA. (Photo credit: Wikipedia)
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."
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