Photo Dennis Crowley, a founder of Foursquare and Chelsa Crowley, a founder of
Stowaway. Credit Winnie Au for The New York Times
"A girlfriend likes to joke that my look is 'aggressively natural,'" said Chelsa Crowley, a founder and the chief creative officer of Stowaway, an online cosmetics company that started last February. "It's natural, but bumped up a notch."
The question was about her makeup style, but her answer was a pretty good description of Ms. Crowley herself: direct, driven and just a little competitive.
She shares a fourth-floor East Village walk-up apartment with her husband, Dennis Crowley, the executive chairman and co-founder of Foursquare, and their two highly social cats, Milky and Sooty.
On a recent chilly Monday, the couple was snuggled at home on the couch: Ms. Crowley, 34, dressed casually in Bloomingdale' s-brand jeans and a Zara cap-sleeve sweater; Mr. Crowley, 39, in Gap jeans and a black T-shirt, liberally sprinkled in cat hair. (His hoodies had been banished, Ms. Crowley said, because they had become too much of a tech-founder cliché.)
The two entrepreneurs, who celebrated their second wedding anniversary in October and are expecting their first child in May, have a uniquely modern marriage. In addition to their cozy home life and shared passion for active sports, Ms. Crowley is a client of her husband's, using Foursquare's location-tracking technology to market her company.
Photo Chelsa and Dennis Crowley. Credit Winnie Au for The New York Times
The Crowleys also cut a dash in New York's tech-social scene, where the most influential people in the room are more likely to be wearing performance fleece than designer suits.
Marcy Simon, an angel investor who became friendly with Mr. Crowley a decade ago and is an adviser to Stowaway, met Ms. Crowley at the Surf Lodge in Montauk, N.Y., a hangout popular with entrepreneurs in their circle. Back in town, the Crowleys' tech set socializes in downtown places like the Soho House in the meatpacking district and Lure Fishbar in SoHo.
"We go out with start-up founders and entrepreneurs," Ms. Simon said of their crowd. "We go out and eat or grab a drink, and then many of us go back to work, whether we have our own start-ups, or we have to talk to the West Coast or China."
The Crowleys' circle includes friends like the entrepreneur brothers Noah and Jonah Goodhart (founders of Right Media and Moat), while encounters at Lure may involve major figures like the Lerer Hippeau venture capital partners Eric Hippeau and Ken Lerer.
Geek mystique gets the Crowleys invited to A-list parties, including the recent James Bond premiere at the Ziegfeld Theater, where they posted an Instagram photo of themselves in black tie. Gossip-column sighti ngs have also placed the Crowleys at events alongside new-media luminaries like Arianna Huffington, the Yahoo chief executive Marissa Mayer and the Hollywood star (and tech gadfly) Ashton Kutcher.
"They are one of the most dynamic and interesting young couples and entrepreneurs that I know," Ms. Simon said of their appeal on the social circuit. "They both make an impact on any room they're in."
On the domestic front, their household conversations may revolve around mundane topics like breakfast or the day's schedules, or can veer into entrepreneurial jargon about geo-targeting customers or C.P.M. (cost per mille, or thousand).
"We have a whole ad product that can identify when people go into a Macy's or a Sephora, and you should put a Stowaway ad in front of them," Mr. Crowley recalled telling his wife one morning, introducing her to Foursquare's Pinpoint service.
"I do my makeup in the bedroom, while he's laying in bed, reading," Ms. Crowley said.
Mr. Crowley shook his head. "I go through my emails," he said. "I'm working."
"He's reading his book," Ms. Crowley said.
"No, I'm not," he said, and paused. "Maybe a little bit."
Such affectionate bickering is familiar to the couple's shared group of friends.
"It's almost like when teenagers really like each other, they're always trying to impress one another by one-upping each other," said Christian Bovine, a longstanding friend who is the user-experience lead at Omnigon, a digital consulting firm. "Whether it's running a marathon or a triathlon, or shooting bow and arrows — all these weird things that they get into — they do it together and they're always pushing each other."
Photo A photo from Dennis Crowley's Instagram account taken at a recent James Bond premiere at the Ziegfeld Theater.
Ms. Crowley started in the beauty business as a makeup artist with Clinique and was most recently an editorial consultant for the cosmetics firm Bobbi Brown. She founded Stowaway with Julie Fredrickson, who had been the digital brand manager at Ann Taylor.
Selling directly to consumers through its website, Stowaway is based on the idea of "right sized" cosmetics: smaller products that are easy to carry and won't expire before the container is empty.
"My co-founder, Julie, and I were chatting one morning over breakfast about frustrations in the cosmetics world," Ms. Crowley said. "She was showing me her bag of tiny little p roducts that she was collecting from every box-of-the-month club. And she was asking me how to get her hands on these products without having to subscribe to all of these boxes."
"I didn't have an answer for her," she said.
Stowaway's Fulton Street offices have the lean ambience of a tech start-up: contractor-white walls, sparsely decorated with watercolors inspired by the hues of the company's product line.
In the conference room, where a stocked bar cart is the most noticeable accent, Ms. Fredrickson said that most customers' first purchase is a $75 six-item kit that includes petite-size lipstick, concealer, mascara, eyeliner, blush and foundation. "We call it the Little Black Dress of beauty," she said.
Also popular is the lipstick ("smaller than your pinkie finger" and "fits in your skinny jeans"), which sold more than 100,000 units over the holidays, Ms. Fredrickson said.
Back in the East Village apartment on East Eighth Street, Sooty and Milky were trying to break out of the spare bedroom, where they had been stashed during an interview and photo shoot. Mr. and Ms. Crowley relaxed with socked feet tucked under themselves on the couch.
"We talk a lot online," Mr. Crowley said of the couple's daily interactions. "The pillow talk, so to speak, is more over instant messenger."
"In the evenings, we're so tired we just need to unwind, and not talking about work is part of unwinding," Ms. Crowley said. "A lot of times, I'm not looking for an adviser in him, I'm looking for a husband, and I just need to vent to him. And he's done this thing where, a lot of times, whenever you freely give advice, it's caused arguments with us …"
"We've learned how to coexist," Mr. Crowley interjected diplomatically.
"And how we've coexisted is, he does this really sweet thing," she said, "which is, he� ��ll ask me, 'Do you want my advice, or do you want me to just listen?' Because, if I say, 'I'd love your advice,' then I've asked for it, and I can't argue."
Perhaps optimistically, she doesn't foresee any such disputes about the separation of roles when their baby comes.
"Clearly, our life is going to change," she said. "But, how we live our life now, clearly all our responsibilities are shared, and everything with the baby will be shared."
Her husband added: "I can't imagine it's any harder than start-up stuff."
