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HowAboutWe's Founders Redefine Online Dating -- And What It Means to Be a CEO

HowAboutWe's Founders Redefine Online Dating -- And What It Means to Be a CEO
Brian Schechter (L) and Aaron Schildkrout (R) went from teaching high school to starting the popular dating website HowAboutWe.

In the middle of 2012, Aaron Schildkrout found himself designing a new homepage for the website of HowAboutWe, the dating site he had founded more than two years earlier. Having pioneered the concept of an online dating site that encourages people to hurry up and start having fun offline -- rather than sticking around to trade winks, hearts, pokes or private messages -- he and his co-founder, Brian Schechter, now wanted to bring couples into the fold. But that was easier said than done. "There was a huge question," Schechter says, "of whether we could create a unified brand bringing our service to the full spectrum of relationships."

What you see now as a first-time visitor to HowAboutWe is a bifurcated homepage, with the product for singles on the lefthand side and the couples product on the right. Take your pick. In the upper right is a unifying tagline: "Get together. Be together."

But when Schildkrout was wireframing the design, he says, "I remember writing 'Fall in love, stay in love' in the upper right, and being genuinely moved by it. Which was very surprising to me. There was a moment in articulating it, the core mission of our company, that felt very true. I felt like it was speaking to what we want as people."

Related: Site Says, 'Make Me a Match: I'll Pay You.'

From that crystallizing moment sprang the new HowAboutWe, separate but united. Since launching in New York in early 2010, HowAboutWe has gained 2.3 million users across both its dating and couples services. The dating site is available nationwide and in 30 countries across the globe, while the couples site has expanded to Seattle, Chicago, San Francisco and, most recently, Los Angeles. The company has raised $22.3 million in funding and now employs 85 people full time.

Its thirtysomething founders had no prior background in technology or business. In their twenties -- which they spent teaching at charter schools, thinking about curriculum design and trying to "reform the American educational system," as Schildkrout puts it -- they would hardly have seemed destined for startup greatness.

A dating app about dates
To hear its founders tell it, HowAboutWe grew out of a realization of the power of the consumer web, married to a deep dissatisfaction with the "inauthentic" ways in which it was being used. "Dating was an obvious area to consider along those lines, in that it was too often characterized by inauthentic poking, endless browsing through lookalike profiles -- a kind of banality and lameness that was unattractive to us and, we thought, many millennials," Schildkrout says.

Best friends and now co-CEOs, Schildkrout and Schechter have known each other since they were kids in Boston. Schildkrout stayed in Boston to teach high school students, while his friend ended up teaching in Washington, D.C. But by the summer of 2009, both had left their jobs, knowing they wanted to start a consumer web company. That's when they did something unusual for would-be tech entrepreneurs: They pulled up stakes and headed to Europe. For two months they traveled through Turkey and the Balkans. The idea, Schechter says, was to get "some real head space to think deeply about what's happening with the internet."

At the time, Twitter, Groupon and Foursquare were beginning to come into their own. Facebook's initial public offering was still three years away. But the men's quixotic journey failed to produce any workable ideas. "Our various ideas were dashed against the rocks of our own pragmatism," Schildkrout says. (He believes it is essential for founders to balance "intense, unrelenting honesty with dreaming.") Not until they were back in Boston, hanging out at Schechter's dad's house, did the idea of HowAboutWe arise from those months of relentless self-criticism. "Why isn't there a dating app that's actually about dates?"

Related: 5 Challenges of Being the First to Market

Other dating sites, like Match.com and eHarmony, put too much emphasis on the online component. Schechter and Schildkrout thought they could do better by shifting the emphasis back to the real world, where dates actually take place. What's more, they thought online dating was at a tipping point, about to move from being stigmatized to being mainstream. At first, they worked out of Schildkrout's mother's house, bootstrapping the business with their savings. By the spring of 2010, though, they had raised seed funding from angel investors, friends and family and had left Boston for New York. The site was on its way.

Teaching and leading
On a recent Monday afternoon, the two founders sat down with me in one of three office spaces they occupy on the ninth floor of a building in Brooklyn's Dumbo neighborhood. It was a cold day, but the sunlight streaming through large windows raised sweat on our faces. Outside was a view over the East River, toward Manhattan. Behind me was a kitchen stocked with free food -- an essential perk in modern startup culture. There were pretzels, crackers and potato chips; peanut butter and whole-wheat bread; cheese, cold cuts and organic fruit delivered by FreshDirect. Less than four years after launch, life at HowAboutWe was good.

We began discussing a topic near and dear to both men's hearts: the similarities between being a teacher and being a CEO. Schildkrout, who has a short beard and dark hair sprinkled with gray, wore a blue sweater with the sleeves pushed up on his forearms and thick-framed glasses. His voice was relaxed, his eyes intense. There is a misconception that teaching is something fuzzy and progressive and not rigorous, he says. By his last year as a teacher at the Codman Academy Charter School in Boston, he was giving his students 10 to 20 grades per class, which he added to an online grading system that was accessible to the students. In an unpublished essay, Schildkrout writes, "The kids got addicted to checking their grades. I had essentially created a real-time metrics dashboard for my students and for me."

Related: Forget Love: Your Future Co-Founder Could Be Waiting for You Online

He brings a similar obsession with data to HowAboutWe. "I get 20 of these every single morning," he says, showing me a table of figures on his phone that displays the results of a feature test. When the company wants to find out whether a new site function or design feature will be well received by users, it runs a test -- making one type of function available to some users, and another type available to others. Although he keeps most of the specifics to himself, Schildkrout says these tests go much deeper than the superficial "red button vs. blue button" tests run by many web companies.

In his essay, Schildkrout draws parallels between curriculum design and product design, between motivating students to learn and motivating employees to sell. To be effective, both teachers and business leaders need to keep a weather eye on crucial metrics, constantly measuring their progress. Both can be lonely jobs, he says. No matter how good your support staff, at the end of the day you're on your own. "Teaching is more like being a CEO than our teacher-degrading society wishes to know," he writes, "and being a CEO is a lot more like being a teacher than our CEO-mystified society understands."

Transformational work
Every Sunday, HowAboutWe's founders send out one staff email apiece, each to his own departments, as a way to reflect on the past week and think openly about the week ahead. (Schechter, the optimistic yin to his partner's more cynical yang, oversees sales and marketing, while Schildkrout is responsible for product and design. A few employees receive both emails.) Some of the emails focus on specific goals or projects, while others indulge in "philosophical musings on the nature of work and productivity," one employee tells me.

Related: How Leaders Can Find Their Mojo

A teacher never stops teaching. Michelle Dozois, who in June 2010 became the company's first hire, says that in the early days meetings often took place late at night in Chinatown restaurants. Her bosses were roommates by then, and they lived in the neighborhood. Schechter and Schildkrout continue this tradition as an informal leadership development program, taking core staffers out for dinner or drinks.

And they have adapted methods of student-directed learning -- in which teachers allow students to take the wheel and determine what is important to them in the classroom -- to the tried-and-true company meeting. HowAboutWe retrospective meetings, or "retros," a cornerstone of the company culture, are organized around three categories: things that are going well, things that are not going well and things that should be changed. In retros, employees are completely open about everything from a shortage of snack food to instances of subpar marketing copy. Everyone is heard.

HowAboutWe's co-founders share a belief that it's their responsibility to make work meaningful for employees. "Your employees are spending the majority of this part of their life working in your company, and we only have so long on this planet," Schildkrout writes in his unpublished essay. "So everyone's experience of work should be transformational. It follows that your job as CEO is to make this the case."

Heart plus brains
HowAboutWe itself is undergoing a transformation. Last month, it launched a lifestyle media network and advertising division. As part of this initiative, HowAboutWe acquired Nerve, an online magazine devoted to love and culture that launched in 1997. It also debuted Swimmingly, a standalone website for couples ("lifehacking meets home design," Dozois says), and Famously, which is focused on entertainment and celebrity. HowAboutWe's long-running Date Report, formerly a blog for singles, got a makeover just like Nerve.

Dozois, who started as the company's community manager and has had several title changes since, is now the editorial director overseeing this new venture. Seventeen bloggers and editors work under her, along with a network of freelancers. When it came to staffing up the new division, Dozois, tried to follow the example of Schildkrout and Schechter. "They hire brains rather than narrow specific roles," she says.

Heart plus brains is the recipe by which HowAboutWe has built a successful web company atop the zeitgeist of modern love. (Schechter was once fixated on the idea that HowAboutWe's logo should be a couple dancing on a rooftop.) Along the way, some of the company's efforts have failed, like Flrty, a Facebook app that garnered so many spam complaints that Facebook banned it. "We tried to relaunch it a few times, but it remained caught in Facebook's anti-spam trap, and it never got out," Schildkrout says. "So we killed it." But the company's core mission remains unchanged.

"Nobody's saying that this is about love. But this is really about the fact that you want to fall totally, madly in love with somebody in your life and stay in love with them," says Schildkrout, who has been in a serious relationship for the past year. "That's one of the coolest things you can possibly do in a human life, and we're just gonna say that."

Related: Are You a Good Leader? (Infographic)

Brian Patrick Eha is a freelance journalist and former assistant editor at Entrepreneur.com. He is writing a book about the global phenomenon of Bitcoin for Portfolio, an imprint of Penguin Random House. It will be published in 2015.

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