Four days after the election of Donald Trump, the former CEO of a failed anonymous social media app tweeted: “Secret V2 is coming. It’s too important for it to not exist.” About a year and a half earlier, Secret had shut down, overwhelmed by an epidemic of cyberbullying and competition from Yik Yak. But as America woke up to the fact that polling and data had failed to capture the political leanings of the country, the power of the unspoken was more apparent than ever. Shell-shocked Democrats were viewing their more right-leaning friends and family with newly skeptical eyes, wondering if they had kept quiet on mainstream social media for fear of being attacked. Meanwhile on Reddit, a community of diehard Trump supporters had swelled to some 270,000 subscribers—now nearly 380,000—sharing memes, discussing their fervor for Trump and dislike of Clinton, and, yes, penning some loosely coded bigotry under the shelter of anonymity. There, legions of Trump supporters felt free to express their opinions. But a liberal voter who didn’t know to visit /r/The_Donald might never see those points of view. That kind of disconnect raised a question in the mind of Secret’s former CEO, David Byttow: Would the world look notably different to us if the people in our social networks didn’t feel like they had to censor their thoughts?

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The original Secret app, which launched in early 2014, allowed users to post anonymously and view anonymous posts from their friends, in what Byttow envisioned as the “anti-Facebook, where you can actually say shit that represents your most authentic self, as opposed to your best self.”

At their height, Secret and similarly anonymous apps like Yik Yak and Whisper were hailed as the future of social media — an antidote to the real-name controversies on Facebook and the highly polished, hyper-curated look of Instagram. Anonymous apps harkened back to the bare-bones message boards that brought early internet culture to life, but reinvented them for the social network age. Yet despite a collective $200 million in funding, anonymity has remained a kind of kryptonite for social apps. The reason is simple: An online social network serves one purpose, to connect people. Without names attached, people’s words become either mean — or meaningless.

When they first showed up, identity-free social media apps were a viral hit—including on my own college campus. For most of my time at college, anonymous discussion was limited to the “anonymous confessions board,” a rudimentary forum moderated by, to the best of anyone’s knowledge, a single student. The ACB wasn’t wildly popular, and it carried a certain stigma; it was the kind of site you’d delete from your “top sites” to avoid getting looks from your neighbors in the library. Once, I used it to find a lost coat.

Then in the fall of 2014, Yik Yak took off — and the ACB went quiet. Suddenly, it seemed like every student was on the app, filling it with snarky one-liners, observations, party promotions, and, at times, malicious gossip. My friends and I gleefully texted each other screenshots when one of our Yaks made it onto the “hot” page and earned hundreds of upvotes. It was the perfect procrastination tool — the ACB gone mainstream, and gussied up with a slick design. Yik Yak, of course, had even loftier ambitions, envisioning itself as the Twitter of the younger generation.

Meanwhile Secret exploded in its own right, gaining notoriety as a hub of insidery, Silicon Valley gossip — the kind of place where one might go to spread rumors of an Evernote acquisition, or discuss which startups use marijuana as an interview intimidation tactic. Secret and Yik Yak grew quickly, raising $35 million and $73.5 million respectively in their first seven months. They were highly addictive: Byttow says that to this day, people tell him they would compulsively delete and reinstall Secret, their desire to stop wasting hours on the app at war with their FOMO. He hoped to build Secret into a genuine rival to Instagram and Facebook, and for a time it seemed that his dream might come true: After scoring its first taste of virality in its birthplace of Silicon Valley, Secret went on to snag the #1 app store download spot in eight countries.

But with popularity came a greater chance of error — and more scrutiny. As Yik Yak spread across college and high school campuses, parents and administrators grew concerned that it was facilitating cyberbullying. Schools started banning the app from their networks and begging students to delete it from their phones. Secret, too, proved extremely difficult to moderate as its user base expanded. Byttow says the team “couldn’t contain it, could not control it, and it caused us to lose sight of that original vision.”

The negative posts, not the apps’ other attributes, came to shape their reputations. “Suddenly you had a lot of people spending a tremendous amount of time engaging in activities on these anonymous apps,” says Karen North, the director of the University of Southern California’s digital social media program. The discovery of the apps’ dark content kicked off a flurry of negative press. “It was the problematic behaviors that made it newsworthy, rather than the anonymity of it,” says North.

Both companies scrambled to clean up their posts. Secret built out a team of 90 full-time moderators, but still found that effective moderation demanded resources it couldn’t muster. Because the app centered around friend groups, abusive content could be nuanced or coded, and moderating it required understanding the context of the social group in which it was posted. Yik Yak made more drastic design changes—and discovered that its actions alienated users. In August of 2016, Yik Yak made its formerly optional “handles” mandatory, under the idea that pseudonyms would make users more accountable for their posts, curbing trolls. Users protested, arguing that handles were “contrary to the whole idea of Yik Yak.” The company backtracked in November, apologizing and making handles optional once more, but the damage had been done. The app’s core users, who’d flocked to it in part for the salacious content only possible under total anonymity, had lost interest. When I checked in on my alma mater’s Yak scene recently, the posts on the “hot” feed, once decorated with hundreds of upvotes, topped out at about 30.

Whisper, meanwhile, neither rose as high nor fell as far as either Secret or Yik Yak. It aspires to be a social network that doesn’t rely on a social graph. The app has features for finding people nearby or forming groups, but the feed defaults to showing users popular posts from all over the world. The result is far less deeply offensive material—which may be the reason for Whisper’s staying power. “If you want to be mean to someone, it’s important to you if they see it — there’s no point in it if they’re never going to see the post,” says Jeremy Liew, a partner at Lightspeed Ventures, which led Whisper’s $3 million series A funding round. It’s much less satisfying to be a bully if your victim doesn’t ever notice.

Whisper has tackled its own moderation challenges using a machine learning system it’s dubbed “The Arbiter,” which automatically removes posts that violate its guidelines. A huge safety team of over 130 people is also on hand to address higher-level flags that the AI might miss. But without links to friends or relevant communities, Whisper has a major problem: It gets boring, quickly. The app is clean, civil — and wholly irrelevant to most people.

In April 2015, Secret folded. By December 2016, Yik Yak had laid off 60 percent of its staff, and last month The Verge reported that the company is pivoting toward a non-anonymous college course collaboration chat app. Whisper, meanwhile, has rebranded as a “media company of the future,” and is currently the 86th-most-downloaded social networking app in the iOS store — right below an obscure app that claims to help users gain free Snapchat followers.

From the bulletin boards of the early internet to the subreddits of today, anonymity has always had a place online. But as Secret, Yik Yak, and Whisper all discovered, anonymous social networks are something of an oxymoron. An anonymous app that relies on social connections to be relevant all too easily breeds foul behavior, and quickly becomes antisocial. An anonymous app that lacks real-world social or geographical ties, meanwhile, struggles to be addictive. What does work, more or less, is an anonymous or pseudonymous group that forms around an interest, where a person’s identity matters less than their willingness to engage on a shared passion.

In Byttow’s view, a fatal flaw of anonymous social media is that using the apps doesn’t pay dividends. Users can’t build relationships or burnish their own reputations while operating without names. From time to time, people may have a piece of information they’d like to share with the world without revealing their identity, but that’s not enough to sustain a network. What makes an app sticky is positive reinforcement: more followers, more friends, more retweets. “For the most part people want to communicate with an audience,” says North. “People want credit for what they’ve said and done. Anonymity flies in the face of people’s need to have acknowledgment.”

Still, Byttow is trying again, with the second coming of Secret. He’s now developing it as a side project, so many of the challenges remain unsolved. He plans to make it invite-only, to keep it intentionally small and manageable. That would surmount the moderation challenge, and maybe help it retain a sense of community—for the time being, Byttow says he’s “interested in soon at least using it with my friends, and seeing what happens with it.”

In setting their sights on becoming the anti-Facebook or Twitter for Generation Z, the builders of anonymous social media apps made a number of miscalculations. The biggest might well be the fact that their reward systems, such as upvotes, don’t extend to real-world identities. At least that was the case for me: After enough of my college-era Yaks made it onto the hot feed, I got tired of texting my friends screenshots…and started tweeting, instead.