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Featured on Feb 03, 2011

Brian Schechter

"...all in all and on the whole: some day I wish to be only a Yes-sayer. - Nietzsche"


I secretly want to be a theorist for the new Humanism. Starting a business seems like an essential first step. The background: I grew up in Newton, MA., down the street from Aaron Schildkrout - the other Co-Founder of HowAboutWe. Between 16 and 20, I became passionate about urban education, theology and all-things fun. From 20-30, I dove in to these passions, leaving all-things fun to the side more often than not. At 31, I started working on HowAboutWe with Aaron. And now, to my constant surprise, I am passionate about getting people to know about HowAboutWe - the only dating site out there I'd want to use.

  • Title: Co-Founder and Co-CEO of
  • Age: 31
  • Location: LES
  • Contact: @bschech

You co-founded HowAboutWe with your childhood friend, Aaron Schildkrout, and your dad is an advisor, what are some of the pros and cons of working with “family” day in day out?

Having my dad as an advisor has been invaluable for our business, and it's been an amazing thing, as a son, to experience personally.

The pros: he's been through it... empathic to the highs and the lows; astute when it comes to what is and is not a big deal; connected when it comes to networking and pretty wise when it comes to the important stuff - timing, hiring, cash-flow, core strategy, etc.

The cons: we can get pretty all-consumed with HowAboutWe and forget to find traditional father-son time.

I've also gotta add here that we've gotten tremendous support from all our family members. Aaron's mother is basically the conscience of the HowAboutWe product and watches google analytics more than Aaron and (I) combined.

What other ideas did you and Aaron kick around besides Waymark, for finance + for lifestyle, before you guys decided to build HowAboutWe?

Hah. So first, Waymark is still an amazing idea and it was way bigger than Mint + UrbanDaddy. It was a little more like Facebook + Life-Enhancing Value (not just ego-boosting, at times, distractions).

The origin of the term Warmark was hiking in Turkey - looking for red and white "waymarks" to guide our way. And WayMark was supposed to be like that…like a trail-guide.

And then there was MyXi (short for my information, a personalized stream of life-style information); and then we had a business idea that I'm not going to explain here but the tag line is "Where everybody wins.

We thought about a new kind of search engine (really before I even understood what that was) and...then another one called Status. It was all about sneakers, people working in McDonalds and status updates.

There was a common theme in all of our ideas – web-to-world, real life value, activity, information sharing, creativity and applications that would make you say – “Wow, I actually want this.”

The term “online dating” sometimes has negative connotations associated with it, but nowadays everyone from teens to widowers are finding love online. How have people attitudes about online dating changed throughout the years? Do you think HowAboutWe would be as successful if it launched in 2000 instead of 2010?

I think HowAboutWe would have killed it if it launched in 2000. It's a better way to organize online dating. It's easier, faster, more fun, more natural, and more enticing. But the industry has become extremely competitive. I've talked to guys who started sites back in the early 2000's and talk about getting clicks through Google for 5 cents off dating keywords, whereas those same words are like 6 bucks now. And the rates people pay to online date have stayed largely the same.

That said, part of what excites people about HowAboutWe is that they think the site is mirroring something going on in our society - going online to get offline.

HowAboutWe became very popular in a relatively short period of time, is this the first company you've started? Why do you think the site got so popular as quickly as it did? Just the awesomeness of the idea? Great execution? The blog and marketing? What’s your secret sauce?

This is our first company. The initial buzz was definitely about the product and how it resonates with people. Chiara Atik, who used to write for GuestofaGuest and now works full time for us wrote the first piece about us. The title was, "A Dating Site We'd Actually Use." The next day there was a piece in The Frisky, "Finally a non-lame dating site." The idea really sold itself.

But getting in the New York Times, Thrillist, on TV, in Groupon, all of that has required a huge amount of hustle, patience and strategic thinking about how to tell our story.

The secret sauce is that people absolutely want better ways to meet for dates….they want the process to be fun, sexy, easy, enticing….they want it to be about doing things you want to do, creating memories and meeting amazing people. And they want it to be serious. They want to feel like they’re meeting people with whom there’s a real chance that a deep and meaningful relationship could emerge.