Brian Schechter and Aaron Schildkrout – Co-Founders of HowAboutWe

[quote style=”boxed”]We created version 1.0 of HowAboutWe without thinking about or understanding distribution. That was an error. A big, painful error. We learned that filling the funnel is the name of the game. #neveragain[/quote]

Brian Schechter is the co-CEO of

Brian runs marketing and business development and is constantly thinking about how to create a way to use the Internet to find love that reflects contemporary lifestyles.

Brian grew up in Newton, MA, just down the street from Aaron Schildkrout – his best friend and co-CEO. Between ages 16 and 20, Brian became passionate about urban education, theology and meditation. From 20 to 30, he dove in to these passions, teaching high school, volunteering and leading yoga retreats around the world. At 31, he started working on HowAboutWe with the goal of creating a dating site to help people find modern love — a site that he’d actually want to use himself.

Aaron Schildkrout is co-CEO of

Aaron oversees product development and spends his days leading a team of engineers and designers to create a fundamentally new way for people to find love online…one date at a time.

Before HowAboutWe, Aaron was a high school educator at Codman Academy Charter Public School in Boston, MA. Aaron’s work was featured in a variety of publications, including the Gates’ Foundation “High Schools of the Future” curriculum and conferences, Massachusetts Charter School Association publications, the Boston Globe, and the Maury Povich Show.

What are you working on right now?

Making the world’s premier dating site.

What does your typical day look like?

We have very similar days. We each start the work day with a meeting with our teams. Aaron manages the development of our site and Brian manages marketing. After a full day, we both go to the gym, go out on dates (Brian is dating someone and Aaron is just dating) and/or hang out with friends.

3 trends that excite you?

1) Actualism: the rise of a new worldview that merges modernist insights about the value of realism, style and individuation, the premodern recognition of ultimate importance and concern, and a twist of postmodern irony. Something like: a celebration of what’s actually happening.

2) The New Friendship: It seems like people are valuing friendship in a new way. There’s a new openness and jubilance in the air. We like it. Friendship might just be the primary value of the post-millennial generation.

3) The Date is Back: People are going on more – and cooler – dates than ever before. Time for a new kind of dating site.

How do you bring ideas to life?

Wireframe. Test. Talk. Critique. Refine. Share. Laugh. Party. Return to pure focus on filling the funnel. We like surrounding ourselves with people who are smarter, better, and more inspired than we are. We like arguing about what should be done and trusting that the synthesis of our positions will be markedly better than any prior idea.

What inspires you?

Making an enormous company and having the freedom to create beautiful things — rapidly. New ideas. Meditating in the rain on a Vermont farm. Chilling with friends and loved ones.

What is one mistake you’ve made, and what did you learn from it?

We created version 1.0 of HowAboutWe without thinking about or understanding distribution. That was an error. A big, painful error. We learned that filling the funnel is the name of the game. #neveragain

What is one business idea that you’re willing to give away to our readers?

Our first web idea ever: MindSwap. A community where people can share ideas they think are decent but that they know they’ll never use. Kind of like what we’re doing right here. For instance, we come up with funny scenes for movies all the time. All gone to waste.

Why not have a place where ideas can be offered democratically to a community, who then builds upon them. Questions can be asked of the community – by individuals or by brands — and the community can freely offer answers. Credit is the currency. It’s an interesting idea that’s existed in a few different guises, though it’s yet to be well executed. We’ll probably never do it, but we’ll contribute if someone else does.

What do you read every day? Why?

Our analytics reports. The New York Times. And the brilliant graffiti on our street in The Snakehead. Props to “You Would.” (example:

What is the one book that you recommend our community should read, and why?

The Gay Science by Friedrich Nietzsche – a science for happiness and resplendent iconoclasm.

What is your favorite gadget, app or piece of software that helps you every day?

Brian: This is simple, the iPhone.

Aaron: Mt newest favorite thing is SizeUp – magic for anyone managing way too many windows and tabs.

Who would you love to see interviewed on IdeaMensch?

Aaron’s mother. She’s been an ongoing product inspiration and is unusually awesome.

What has most pleasantly surprised you about HowAboutWe?

The date ideas that people post on HowAboutWe exceed, without fail, our best ideas. We tend to think of ourselves as having good ideas – but it turns out that the smartest thing is to create a platform that allows passionate users to express themselves and define the community. Just check out the HowAboutWe date stream and you’ll see what we mean.

You’ve both worked as teachers. Now you’re running a consumer facing web product. How do the two relate?

Classroom teachers are constantly designing experiences for students. The experiences need to guide students to a goal of some kind. Sometimes the goal is very concrete and specific. Sometimes it is lofty and abstract. Every student is different and every day is different. Sustained, repeated, high-value engagement is the key. The tricks of the trade: effective new user experience scaffolding; frequent, real-time feedback; building supportive and generative communities; setting realistic but high expectations; creating experiences that are exciting to get them coming back for more but substantial enough to garner meaningful learning…etc. If you’re a product manager, this will sound rather familiar. Designing web products is hugely similar to designing classrooms. Spending years thinking tirelessly about how to succeed in the classroom (and being punished by our students when our curricula sucked) has been incredible training for building HowAboutWe.

What’s comes next?

Heads to the grindstone, can’t think about what’s next … Yet.

Brian Schechter, @bschech
Aaron Schildkrout, Co-CEO, @schildkrout

[box size=”small” border=”full”]This interview was brought to you by Rohit Jain who works in business development. You can follow Rohit via his blog and on Twitter. [/box]