HowAboutWe Cofounder Aaron Schildkrout thinks you're delusional - Brooklyn

HowAboutWe Cofounder Aaron Schildkrout thinks you’re delusional

An essay from the dating app cofounder offers some #realtalk on how to navigate startup growth strategies. HowAboutWe was recently acquired by IAC.


(Image via

Aaron Schildkrout is a cofounder of HowAboutWe, the online dating site that opted to put experiences ahead of compatibility. It built up a big enough following to get acquired by IAC this year.

Schildkrout wrote an essay for Andrew Chen’s startup newsletter on how he managed to make a new dating site that worked despite the fact that the startup graveyard is littered with dating-site failures.

Here’s some of the top level takeaways from his analysis of the ways in which magical thinking in online dating startups delude founders into inevitable failure:

  • Everybody thinks their site will go viral, but it won’t.
  • See above: Tinder was a unicorn. Also, see below.
  • Entrepreneurs put too much faith in press coverage. It’s less important than you think. (LIES!)
  • If you think you can find partners who will drive you traffic they probably can’t.
  • “SEO: Yeah right.”
  • Advertising is the only reliable, scalable, predictable way of acquiring users for mainstream dating sites.”

If you’re thinking about an online dating business (and really any business where you need to convert individual visitors into paying clients), visit the full essay and read his “Pain Math” exercise. Then do it.

That said, Schildkrout writes that there is one piece of magic that you have to believe in: the magic of your product.

If your product is legitimately special, then that can deliver you to real business success. Tinder — for all you might say about its objectives — is special, Schildkrout writes. It was different.

HowAboutWe, he says, was different. He writes:

At HowAboutWe we created a new way to date based on the incredibly obvious idea that online dating interactions should be based on getting offline. We made dating about actually going on dates, in the real world. This was the newest dating idea since eharmony’s no-search matching algorithm.


The magical belief in what’s special about your product needs to give way to hard business planning as soon as possible, but the product itself is the only bit of magic you should put any trust in. 

Read the full essay  

Companies: HowAboutWe
Subscribe to our Newsletters
Connect with companies from the community
New call-to-action


Technically Media

Sign-up for daily news updates from Brooklyn