(Fling)
Fling CEO Marco Nardone
In June, Fling CEO Marco Nardone was chatting with a would-be venture capital investor, and things were going well.
He reached for the investor's phone to show him how to download their viral messaging app. But one of his executives, also present for the conversation, stopped him, muttering "no, no, no."
A perplexed Nardone made it through the conversation. But when he asked the employee what had him so agitated, he got the worst news that an app startup can get: It had been removed from Apple's App Store.
"It was the worst day of my life," Nardone says.
ChatRoulette phobia
Originally, Fling was a messaging app for iPhone and Android that tried to take you beyond the limits of your own social circle.
When you took a picture or a video, it got sent out to 50 strangers all over the world, and then they could chat and reply to you. Nardone says that it was meant to foster connections between people who would otherwise never interact with each other.
When TechCrunch reviewed Fling at its launch just over a year ago, they found a lot of pictures of male genitalia. But such is the human condition.
In the meanwhile, Fling grew to 4 million users, with over 50 billion messages sent. Celebrities and social media influencers loved it, Nardone says, because they could interact beyond their core audiences. Fling was also finding a following on college campuses.
"It's, I hope, the most viral social network ever invented," Nardone says.
(Fling)
The Fling app for iPhone.
But Apple was nervous about apps that let you chat with strangers, after the bad behavior of users on ChatRoulette made national headlines a few years back and got that app banned from the app store.
So Fling got delisted (not banned, crucially).
As you may expect, this sent the 40-employee-strong Fling into panic mode. The switch was flipped, and Fling was taken offline even for those users who already had the app. The startup didn't want to risk the wrath of Apple by keeping it online — Apple could still ban them permanently.
Nardone called an emergency board meeting. It was obvious that changes had to be made — investors had put around $12 million into the app at that point, and the longer it stayed offline, the more momentum Fling would lose with the crucial (and moneyed) iPhone-owning population.
But because Fling hadn't been fully banned, Apple assigned them a liaison with the App Store and gave them the chance to try again.
Nardone rallied the staff.
For 19 days, every Fling employee worked around the clock, sleeping in the office, trying to build a new version of the app that met Apple's guidelines. Eventually, they made a new app, almost totally from scratch, that ditched the "chat-with-strangers" bit and made it a little bit more like Snapchat, with followers and broadcast modes.