How the Windy City won our hearts

We just got back from a fantastic weekend in the Chicago, where we partnered with Braintree to throw a weekend-long App Challenge. As we continue to recover from the 28-hour marathon of hacking and fun, we thought we’d share some thoughts with the world.

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Chicago’s got it going on

From the moment we left O’Hare, we were welcomed with open arms. Braintree took us into their beautiful office and set us up with workspace for the day, in a treehouse, nonetheless. We’d never speak badly of the community in San Francisco, but we will say that we were floored by the kindness we encountered every minute of our trip – from strangers, new friends and old friends alike.

Then, on Saturday morning things really got exciting. As scores of entrepreneurs filed into the office, the building energy was palpable. From the moment the pitches ended, we knew we were going to see some cool stuff on Sunday.

The projects

After staying up late and waking up early – or, in some cases, never going to sleep at all – the deadline hit on Sunday and it was time to demo. The only rules were that the project was built in the allotted time and that you used one of the sponsor APIs: Singly, Braintree, Tout, Path.To and Venmo. Here are just a few of the fantastic apps:

  • Twizzlio turns your social media connections into a competitive sport. Your social media savvy is tested as you predict which of your own friends, favorite celebrities, and preferred brands will rise in online popularity across Facebook and Twitter.
  • ForGift: Aimed at solving the problem of people forgetting loved one’s birthdays, ForGift tells you who had a recent birthday and makes it very easy to send them some money (with Venmo) and a video postcard (with Tout).
  • Nocti: This mobile app answers the age old question: “What should I do tonight?” By drawing facebook interests, geo-location and more, Nocti suggests the thing you’d most like to do tonight.
  • RacyBike: A mobile app + hardware hack that allows two friends to place a bet on a bike race, and then allows the loser to pay the winner (with Venmo) directly in the app.
  • Blackmail For Friends: Build on the premise that 15 seconds is enough time to blackmail anyone. You shoot an embarrassing clip of your friend, and they receive a message saying they must send you money within one hour or else the video will be posted to that person’s Facebook wall. (Legal review pending)
  • And much, much more.

The results:

Throughout the weekend, we had some bugs filed and fixed, Beau built a new connector for our API (Tout), and one of the teams even committed open-source code to Singly. Beyond all that, we were truly impressed by the caliber of work that was done. Here are the winners:

  • Best use of Singly:
  • Best use of Braintree: YourPhotoWall
  • Best use of Venmo: ForGift
  • Best use of Tout: NFC Geeks
  • Overall winner of App Challenge Chicago: ForGift


This was our first big out-of-town event, and it went very well. In the coming months, expect to see more Singly, in more places!

With more than a dozen prizes awarded, many people walked away from the weekend with cool new stuff. For us, the coolest part was to return to San Francisco with a new community of friends in the thriving tech community of Chicago.

Special thanks to Braintree, Tout, Venmo and for collaborating on this event.

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