In a Pickle? There’s an App for That!

“It started in a cold dressing room, as all great things do,” laughs Evan Katz ’15. The admittedly not-so-snappy dresser texted a handful of female friends, asking them to weigh in on his choice of shirts. An app idea was born.

Pickle, the app product that Katz and cofounder Morgan Steffy offer today, is a far cry from the dressing room idea, though, due largely to a series of successes and failures. Learning flexibility from these experiences, the duo adapted their idea until venture capitalists began to take notice. Their story is one of determination and fortitude, of growing a business in a technology field—with an appearance on the home page of Buzzfeed thrown in for good measure.

Predicting human behavior has always been tricky, but that’s exactly what Katz found himself doing during the app’s development, often correctly but sometimes not. Despite achieving some success with his fashion-based app, he soon realized that users weren’t uploading enough images to keep his voters occupied. Downloads of the app waned. He also saw that users were doing other things with the app, such as loading selfies of friends and asking for crowdsourcing feedback on which selfie was the cutest.

After several product iterations, Pickle was, well, in a pickle, about to crash and burn. Katz uploaded variations of the current app to Imgur, a site for uploading images to seek user votes. An up-vote is good, a down-vote is bad. One mock-up was an app for uploading selfies. “I basically said, ‘If I get 50 up-votes, we’ll build this app.’” Katz’s mock-up got 5,000 up-votes, landed on the front page of the Imgur site, where the most popular images go, and had 2,000 people sign up overnight to get the app when it came out. “That was our first real hit of Internet traction,” he says.

By the time Pickle launched in December 2014, 6,000 people had signed up to receive the app, which involves uploading pictures to compare and seeking user votes to choose the “best” one. Buzzfeed, a highly popular news and culture website, featured it on its home page, describing Pickle as a new app that “lets you pit your selfies against total strangers.” “We had 12,000 downloads that day,” Katz reports.

Still, the app business is a constant series of instant-gratification moments, and finding ways to attract capital and keep users coming back has Katz and his team continuing to find that flexibility is their best friend. “With the app, we need people to use it every day—millions of people. That’s been our challenge all along: How do we make this cool enough that you’ll want to use it the rest of your life?” he says. Thus far, the app has attracted some small investors and, more recently, one large $100,000 investment that will allow Katz and his team a 10-month window to further develop and market Pickle.