Leap was a startup I co-founded to be a platform for challenges with friends that create healthy habits and behavior change. We went through the Brandery, were New & Noteworthy in App Store, and got invited to the Clinton Global Initiative.

I was the design co-founder on a three-person team.

We all contributed to product definition, and I did the design work: the iOS app, branding (except for that dope icon though), and the marketing site.

Originally my buddy James had an idea for a corporate wellness product.

It was that time when corporate wellness started getting interesting, and he had experience seeing the need for some kind of intervention at the company where he worked at the time.

There was an opportunity to bring newer tech and game mechanics to health in a way which helped folks start and maintain healthy habits.

He brought in Ryan to build it, me to design it, and got accepted into the Brandery’s second class.

As we went through the accelerator, talked to mentors, and got feedback from the market, we realized something very quickly:

We were young, didn’t understand sales motions, and were too impatient for sales cycles with HR teams, benefits brokers, and health insurance.

Our energy and experience were in consumer products. So we stripped the product down to a single insight: our experience with the flash diet.

At the time we were, quite ironically, eating like shit.

We knew we had to clean it up so we decided to take on the Whole30 paleo diet challenge. It was a strict 30 days of no grains, dairy, processed food, alcohol, or caffeine.

And though the first week was tough, we crushed it without a slip up.

What was our secret?

In our product research we had come across a study on The Flash Diet. It showed that requiring someone to keep a food diary using photos was more effective than a written diary or giving them more nutrition knowledge.

So we set up a GroupMe channel for the three of us to share pics of our on-diet meals—and to talk trash.

We had a blast, sailed through the challenge, and realized this was what we needed to build all along. Leap was born.

Check out the study:

Leap was, as far we knew, the first app for social group challenges.

We designed the app to combine the Flash Diet research with Tim Ferriss’s four conscious commandments from The 4-Hour Body:

Make your commitment conscious

Make it a game

Make it competitive

Make the commitment small

And while the app was born out of a diet challenge, we supported other types of challenges: diet, fitness, walks, social, and some pretty wild stuff.

Everything about the brand and the app had to be fun—bordering on ridiculous.

With just a few taps you could create a challenge around a goal or interest.

Using Facebook Connect (huge at the time), you could see your friends and invite some of them to join you.

Within each challenge, the primary view was a feed. Each post with a photo and optional caption earned you a point.

You saw the scoreboard update in real time at the top. On each entry you could comment (to keep up the banter) and call a foul (if you felt the post broke the rules.

Because these were subjective social challenges with no oracle, we needed a way to enforce the rules.

Playing into the fun competitive principle, we decided to let the group "foul out" a post. If a majority of the participants called a foul on a post, it fouled out and the submitter lost that point.

At the end of every challenge there’s a winner, and we gave them the opportunity to easily post about their win on Facebook or Twitter.

We launched Leap on Leap Day 2012 (+1 for timing). In the first month:

Featured in Apple App Store

20,000 active users

16,000 challenges created

31,000 photos posted

12,000 twitter backlinks

But things ended quickly.

We weren’t able to raise a seed round after a saturation of consumer social startups. None of us had fundraised before, and after a pivot and a winter of building, we were broke.

We knew what our business model would be: facilitating friendly wagers on challenges (and taking a vig). And, with some scale, we could sell sponsored challenges like Strava does today.

But back then the laws were murky. We needed time and money to build, talk to lawyers, and ship it.

We figured we would ship the app, build some momentum, raise a round, then attack that. Unfortunately, that never came to pass.

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