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Featured on Mar 11, 2011

Aaron Schildkrout

"Try to give people what they would want if they knew what was possible. Or just give them what they ask for."


I'm a co-founder of I spend my days working with an amazing team of engineers and designers to create a fundamentally new way for people to use the internet to find date at a time. Before HowAboutWe, I spent a few years focused on meditation. Prior to that, I was a high school educator at Codman Academy Charter Public School in Boston, MA. (Forthcoming - an article about the similarities between teaching and user experience design.) I went to college at Harvard and grew up outside of Boston.

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

You’ve presented at NY Tech Meetup and have been covered by the NY Times, Gawker, Thrillist, and more. Which type of publicity have you found gets you the most number of new users?

The factors are a) the distribution capacity of the publisher; b) how enticing and accurate the representation of the product is; c) how shareable the article is. The NYTimes article - which was on the front page of the Sunday Styles section - drove more leads by far than any other press we've gotten. There's also a multiplier effect--you see an article in Thrillist, then you read about us in the Times, then you're flicking through Gawker and they say HowAboutWe is the epicenter of the new first date movement...and three times is the charm. Click. Lead. Date.

In his famous class of 2000 Harvard speech Conan O’Brien said that if you ever make a mistake, like giving out the wrong amount of change or forgetting that your underwear goes inside your pants, people will always ask, “And you went to Harvard?!” Do you ever get that reaction? What are some mistakes you’ve learned from in the past?

Hah! No, I seldom get that reaction, but I wish I got it more. In general I love being told about my mistakes. (Probably because my ego thrives on improving so as to ensure that I don't soil the illustrious Harvard legacy.) Uh, seriously though, I've made my good share of mistakes and learned from many of them. Relating to HowAboutWe one mistake I made quite often in the early days of product development was projecting my own needs and wants onto the product trajectory. Yes, there are benefits to building a product that you yourself want to use - but what I long for and what's helpful to me is often different from what others need and want...and, very importantly, from what drives scalable traffic and conversions. I think I'm getting better at working with our team to build a product that's a real match for our market.

Another mistake I've (hopefully) learned from has to do with being a solo act - I used to be a teacher, which is collaborative to an extent but ultimately very much a one-person show. Then I spent time practicing and teaching meditation, which again, in some respects, is quite atomized and isolated. HowAboutWe has been an exercise in teamwork - first with Brian (the other co-founder) and then with our employees. I really cherish the experience of collaborating with a talented team of people who are working super hard towards a common goal--in this case to help millions of people find love by going on awesome dates. It's much more fun with a team.

One mistake I make a lot but don't learn from at all is the deadly combination of impatience, grand expectations, and dogged realism... still working on that.

You're from the Boston-area originally, went to college in Cambridge, and worked in the Boston-area after graduation, yet HowAboutWe was founded in New York and only recently launched in Boston and the rest of the world. Why did you guys decide to start the company in New York? Have you found any interesting dating trends that only occur here?

Well, to begin, let's be honest--a big part of why we started HowAboutWe in NYC was because we wanted to live here. That said, we also felt like it was the right place to launch--if we could build a viable Internet dating business in the most style-conscious, saturated, expensive (particularly in terms of paid customer acquisition) city in America...well, that'd be good. Also, when we got here we realized that the NY tech scene was exploding; we've been incredibly supported by the vibrant and generous tech / start-up community.

As for dating trends...New Yorkers are damn good at proposing dates! They're smart, savvy, and active. Every time I go to the date search page on HowAboutWe in NY I get all excited...all these attractive, intelligent, authentic people saying what they really want to do. Tens of thousands of them. I remember early on, we had manually created a database of NY date ideas to give people support in coming up with proposals. Then the site launched and I started reading people's dates and was like---ah, I see, our users are just way better then us at this--more creative, more knowledgeable, less cheesy. This is true everywhere, but particularly in NYC.

Do you have any advice for other teams of non-technical co-founders building a web-based business?

Find someone like John Pignata--our amazing CTO. Seriously.

That withstanding, I do think it's possible, but difficult.

Some simple things first: 1) You've gotta quickly learn how to talk to technical people. Understand the basics of how web and mobile apps are built and the core choices you'll need to make as you work to manifest your idea. Don't be afraid of cold calling people and just asking for help. Whitney Hess, a brilliant NYC UX designer, always reminds of when Brian called her out of the blue from Boston and said, 'I'm wondering if you can tell me how to build a website.'. Whitney is still helping us with that.

2) Hire and pay a very smart technical person who has executive management experience to help you make the early decisions regarding hiring, outsourcing, etc. Win over someone really talented with your enthusiasm and chutzpah. It will ground your decision making, diminish anxiety (which is essential to productivity), and provide a compass for execution.

3) Become an awesome product manager. I think learning how to effectively but roughly wireframe and spec out your idea and manage an agile development workflow is essential. It took me about a year to brgin to really get this--but if I had found better teachers I think I could have learned a lot of it in a week. And that would have saved tens if not hundreds of thousands of dollars, months of development time, and a ton of stress. I don't even think I'm exaggerating here.

Now some other advice to nontechnical (or technical) cofounders. Relentlessly attack your own idea. Make sure it's really good--or really could be good. Is there a real market for it? (And just because people say your concept is cool or smart or dope means NOTHING about whether they will use, buy, and share it. ). Do you have distribution solved? Do you really know how it will spread...very mechanically? Where's the cash? If other people are doing it and you have a different spin, do you really understand the customer acquisition dynamics at play? Etc. Relentlessness, with the willingness to say - this isnt it, we aren't there yet.

Second, I think that as important as technical expertise is product insight, willingness to work until you can't keep your eyes open, communication and networking skills, readiness to ask for help, marketing and distribution understanding, etc. The virtues of the entrepreneur. All of which can be cultivated.

Probably the most important factor to early success is learning speed. You've really got to learn so fast. The speed at which you learn and the speed at which you are running out of money are in a battle. Win!