On Falling In Love In “The Real World”: A Q&A With Aaron Schildkrout, Co-Founder of HowAboutWe

Aaron SchildkroutAaron Schildkrout cofounded dating site HowAboutWe four years ago with his longtime friend, Brian Schechter. HowAboutWe began as a site for singles to meet each other and plan dates. Now, it’s expanded to include a service that helps couples plan dates, as well as a series of popular blogs.

The Observer caught up with Mr. Schildkrout to find out what it’s like being the leader of a successful online dating service.

What originally motivated you and Mr. Schechter to found HowAboutWe?

Our core motivation in creating the company was the strong experience that online dating sites were broken —that they were focused on keeping people online and subscribed, rather than offline and in love. And we wanted to change that. That was the original impetus.

We set out originally to solve the “stay online problem” by building HowAboutWe Dating, which was all about getting offline and meeting in the real world, where we thought actual chemistry happened. We did that by building the site around first dates. People suggested coffee shops they wanted to try out, rooftop bars, shows they wanted to see. They could connect and get offline.

So how did you decide to make HowAboutWe for Couples?

[Couples were saying], “Hey, we’re stuck in a rut, we keep going to the same place again and again, we’re looking for something fresh and new in our dating lives. But we’re also really busy, and we don’t feel like spending a million dollars on dates. Help us.”

So we created a product designed to make date night happen. We go out and find the best possible value for your date experiences. We make the booking process and the reservation process extremely easy — you never have to show a voucher, your name’s already on the list. We do all the work for you. We take care of all the details.

Have you expanded in any other ways?

We created HowAboutWe media, which is the third division of our company. We had created a company blog called The Date Report that accrued a lot of organic traffic, and we realized there was a major gap in the media industry around content focused on love, relationships and sex. While there is a Food Network and a Sports Network and a Style Network, there is no network for love content.

It organically grew to somewhere close to a million uniques. People had a deep hunger for that kind of content. So we acquired Nerve.com, and launched two additional blogs. We built out a world-class editorial team, and for the last three months, we’ve been working really hard to create a media wing focused on becoming the authoritative voice on all things love, and have grown traffic dramatically in that process.

Do you think it’s a good idea for all tech companies to start blogs?

No. I think very seldom does content work as a strategy for tech companies. But when you hit a sweet spot where the content is deeply desired by people and is in alignment with your core strategy, it can work really well. And it’s worked really well for us.

Why do you think people are using HowAboutWe to find love, as opposed to other popular dating services like OkCupid or Tinder?

I think if you want to fall in love in the real world, you go to HowAboutWe. If you want to inject yourself into a mathematical matching algorithm, you might to go OkCupid. If you want a lighter weight, more sex-oriented experience, you might go to Tinder. If you want something more traditional you go to eHarmony or Match.com. But if you’re a person living in a city who really wants to find an actual, serious experience, and who wants to do so in a fun, authentic way, HowAboutWe is the best solution.

Are there any leadership tactics unique to running a dating service?

First of all, almost every dating company that’s ever been created has failed. Out of the last eight years, with the exception of companies owned by IAC, I think HowAboutWe is the only successful dating company that’s been created. Tinder is owned by IAC and they’ve done a great job, but other than that, you’d be hard-pressed to name a single other innovation in dating.

[So] you have to have a great product. People are searching for their most important relationship through your product, so it needs to be great. Secondly, you need to be differentiated. You need to really innovate. We created an entirely new category by creating a couples’ product, and by making online dating focused on offline.

You [also] have to be very good at customer acquisition. From a business perspective, dating is a business with a classic empty room problem — if you don’t have great customer acquisition to start, no matter how wonderful your product is, nobody’s going to use it.

And then fourth, I think brands and branding is extremely important — particularly for a product that is trying to help people in such an intimate, emotional way. That’s a competency that you need to have in creating a dating and relationship company.

And then the fifth thing applies specific to dating — it’s an extremely data-driven industry. And so everything from matching algorithms to advertising dynamics need to be driven by an extremely sophisticated approach to data.

HowAboutWe is based in DUMBO. What’s it like working there?

[We] love it. It’s been an important part of our company’s growth and core ethos. I think it’s an extremely creative place. We’ve been here for almost five years, and have seen DUMBO really become a center of tech, design and innovative thinking about modern product. It’s helped us to attract great talent and build out a world-class team.

Do you ever get to see, firsthand, the successful relationships that come out of your product?

I’ve been to weddings. We get people writing to us all the time that met on HowAboutWe, and [now use] our couple’s product. It’s awesome, probably the most gratifying part of the whole thing.