Names: Aaron Schild-krout and Brian Schechter
Jobs: The 34-year-old co-founders and co-CEOs of next generation dating site HowAboutWe call the business “the first company dedicated to helping people fall in love and stay in love.”
Initially, the duo focused on providing a forum for singles to post their dream-date ideas and connect with each other offline to make it a reality. A year ago, they introduced a second site, HowAboutWe Couples, which provides a curated selection of couples’ activities to help solve the “ordering Chinese and Netflix every night” dilemma.
The childhood friends, who grew up near Boston and worked as teachers after college, launched the business in 2010. They’ve raised $22 million so far to power their vision. They boast more than 2 million users across both sites and are in the midst of rolling out internationally.
The entrepreneurs’ hip, open-plan office in booming Dumbo is modern and seems to be populated entirely by 20-somethings.
The pals have a lot in common, including statement socks — Schildkrout offsets a gray sweater and gray pants with purple plaid socks, while Schechter, in a blue button-down and jeans, dons pink.
Schildkrout, a curly haired Harvard grad, says he and Schechter were inspired to create a dating site based on real-world experiences after their own “dehumanizing experience” trying other dating sites. Schechter is single, but Schildkrout is now in a relationship.
Routine: The entrepreneurs’ skills complement each other: Schildkrout oversees the meat and potatoes of the site (product design and strategy); Schechter handles the business side (promotion and partnerships).
They arrive by 9:30 a.m. Their days are typically meeting-filled, so they’re away from their desks the majority of the time.
One of the perks offered at HowAboutWe is catered lunches on Mondays and breakfasts on Fridays, as well as a fully-stocked kitchen, so the co-founders usually have lunch in the office dining area. When they do venture out, they hit Dumbo food trucks and haunts — Foragers, Mexico Blvd., reBar, and Superfine, among others.
They leave work “when the inbox is empty” — which sounds like never, but Schildkrout claims they’ve “gotten better at work/life balance over time. It’s about efficiency and prioritization.” He goes on dates with his girlfriend and squeezes in a workout at Equinox in Soho. Once a week, the partners meet from 5:30 to 8 p.m.
Décor: The 6,000-square-foot space on the ninth floor is sunny and streamlined, with a wall of oversize windows providing views of Dumbo. It’s divided in two, with offices situated on either side.
The choppy setup is a by-product of the startup’s rapid growth. The primary area is home to the tech, product development and finance teams. The secondary office is predominantly editors scouting for adventurous dates and packaging their finds to make them appeal to their active, tech-savvy audience.
One wall of the space showcases colorful images of the site’s dates — from a dumpling-making class in Tribeca ($115) to a fencing lesson in Harlem ($45). Tongue-in-cheek descriptions package the product. “How About We express ourselves on the mat and on the canvas?” is the come on for a Brooklyn-based yoga and art class ($85).
Desk: The CEOs sit at facing light-colored birch Ikea desks. They say they see each other for a combined 45 minutes a day on many days.
Schechter has a real-world inbox with a handful of documents in it, and a giant B — for Brian — that
Schildkrout bought him online. A bonsai and lavender sachet create a mini Zen zone. Schildkrout has three pieces of paper on his desk. “That feels to me like a problem,” he says. “My ideal is to leave the office with my inbox at zero — and that includes my e-mail’s inbox. I’m an aggressive archiver.” A U-shaped magnet, a gift from Schildkrout’s girlfriend, is one of the few occupants permitted in the space.
Commute: When the pair first moved to New York City three years ago, they were roommates on the Lower East Side. Schildkrout stayed in that neighborhood — it takes him 18 minutes to get in. Schechter moved to Nolita and skateboards to work.