Michael Heyward is scouring the web for military secrets, though not of the Julian Assange variety. Over black tea at a dark hotel bar in downtown Los Angeles, Heyward and I sit next to each other, noses to a laptop as he searches on Whisper, the mobile service he created that lets anyone share their innermost secrets anonymously. He's using an internal company tool called Predict to dig up Whispers on specific topics—in this instance, about soldiers who are agonizing over their sexual preferences. Heyward zeroes in on locations like Kandahar and Bagram Airfield, in Afghanistan, soon landing on a Whisper from a bisexual Marine near Kabul who is afraid to come out to his platoon. "This guy thinks he's the only person on the planet with this emotion, but there's no reason he should feel alone—tons of people are like him," says Heyward. "We created this place so you can connect with people. It's like a Wikipedia of human emotion."
To share Whispers, users pull up the app on their smartphones and type out a short message, choosing a relevant stock image to serve as a backdrop. The unsigned missive is then visible to the Whisper community, displayed on feeds that can be sorted by popularity, geographic proximity, and so forth. Whispers range from disturbing to heartwarming, from enlightening to asinine. You can reply with your own Whisper or even have private chats with other Whisperers. It's a smartphone confessional that's caught on with millions of millennials, who now flip through an eye-popping 6 billion Whispers per month.
Whisper is at the forefront of a new category of online sharing—one in which content is revealing, authentic, and most important, untraceable. Since Whisper launched two years ago, the anonymous-sharing space has exploded, with competitors such as Yik Yak, Secret, and Wut all vying for the nation's guts-spillers. To Heyward, 26, these services represent a cultural reaction to this age of NSA snooping and data collection, a world that has given rise to Edward Snowden, Assange, and hacker collective Anonymous. People still have a strong urge to reveal their deepest emotions: teenagers worried about never losing their virginity, veterans who struggle with PTSD, or women frightened of an abusive spouse, all of whom commonly show up on Whisper. But digitally savvy sharers are increasingly worried about possible repercussions of such online confessions. "There's more understanding of this concept of a 'digital footprint' than ever before," says Whisper's founder.
Heyward grew up in Beverly Hills, California, the son of a successful television executive and a stay-at-home mom. He "really, really always hated" school, so much so that he didn't bother applying to college, and when he was 18, Heyward went to work in the interactive division of his father's company, DIC Entertainment, which created popular children's TV shows such as Inspector Gadget and Speed Racer. He says he was always looking for "larger-than-life opportunities," and though in some ways he was foundering at the time, his ambition was evident. His big idea was to buy the U.S. television rights to Formula 1 racing, a project he put three years of work into. While closing the deal, he grew close to a co-worker and neighborhood friend named Brad Brooks. In 2010, when Brooks left to start a company called TigerText, Heyward followed.
TigerText made a name for itself in part through self-destructing messages for businesses. There was something "unshackling" about this concept, according to Heyward, who started to notice how inherently inauthentic and vain the posts were that he and his friends shared on Twitter, Instagram, and other identity-based networks. "What we see from our friends is this superglossy version where everyone's having fun and everyone's so cool, while I'm just sitting here in bed looking at Facebook. But that's what everyone else is actually doing too."
With Brooks as a cofounder, Heyward started WhisperText LLC. His aim was to go after the unshared "whitespace"—say, the emotions you might feel when you don't have a sweet Instagram photo or tweet to share on Saturday night. He was inspired in part by PostSecret, a popular blog from the mid-2000s that collected anonymously sent, emotionally revealing postcards and put them online for all to see. Whisper launched in the spring of 2012 and quickly became popular among young users who found the experience to be equal parts therapeutic and voyeuristic. "People use our communication medium to share secrets, meet new people, and get advice like, 'I'm 24 and I'm going bald—what do I do?' " Heyward says.
Over the next two years, the company raised $60 million during three big rounds of funding, the most recent of which closed this past March, involving some of the same investors who backed Instagram, Snapchat, Tumblr, and WhatsApp. The question now is, How will Whisper build a business based on anonymous interactions? Heyward doesn't appear fazed at the prospect of living up to his service's hype. "Obviously, building any business is really hard," he says. Whereas executives at other hot tech startups would likely endure torture before acknowledging that their business is based on traditional, old-world advertising, Heyward is up front about how Whisper will generate revenue. "Not unlike Facebook and Twitter, we're a media company at heart; we service content to a lot of people, and generally that turns out to be a great ad business," he says. "There's no business on the Internet that has achieved web scale—50 or 100 million users—and had a problem making money."
He cites LinkedIn as his inspiration, a company that has made a killing off of targeted advertising while offering premium tools to its users and building up a strong editorial platform optimized to attract eyeballs to its network. To that end, Heyward recently hired Neetzan Zimmerman, the former Gawker star known for producing viral content, to serve as Whisper's editor-in-chief, as well as Eric Yellin, Hulu's former VP of marketing and distribution. Together, they'll work to curate viral Whispers and team with partners like BuzzFeed to bring more attention to the service's best secrets.
Still, Whisper's future isn't without uncertainty. A slew of competitors are hungering for the same whitespace Whisper plays in, and it wouldn't be difficult for Snapchat or Facebook to launch similar anonymous-sharing features. The biggest challenge for Heyward will be to keep Whisper's content fresh. "The problem with anonymity is that the conversation tends to degenerate over time," says Andreessen Horowitz cofounder Ben Horowitz, who has not invested in Whisper. "That's been the history [of anonymity on] the Internet: It starts off great, but then it gets so ugly that nobody wants to be there anymore." (His VC cofounder Marc Andreessen got into a public Twitter fight with Heyward several months ago on the same topic.)
Heyward has tasked more than 130 moderators with keeping the Whisper community safe, supportive, and free of haters. He has also banned the use of proper names on the platform, "so someone can't be like, 'Becky Smith is cheating on John Adams.'" (Exceptions are made, controversially, for public figures.) So far, that effort has worked. "From the very beginning, Michael was so thoughtful about the culture and put safeguards into place [to protect against] bullying and name-calling," says Lightspeed Venture partner Jeremy Liew, one of Whisper's first investors. "That's what separates him from so many other entrepreneurs, who have built [services] on the idea of anonymity—from Chatroulette to YouTube," some of which have become "a cesspool of racism, misogyny, and general unpleasantness."
In May, Whisper released a more polished version of the app that allows users to search for secrets related to specific areas of interest (such as parenthood or celebrity gossip) or locations (such as Sand Hill Road or Wall Street). Heyward believes the personalized content will help attract an older audience, which may have gotten lost in the avalanche of youth-oriented secrets that typically greet users in the main feed of what's trending. For the most part, Heyward is still figuring out what Whisper will become. Not long ago, he found himself getting frustrated by people who kept sharing Whispers featuring sappy questions. "'If you could ask God one question, what would you ask?'" he quotes. "I was like, These people are so annoying!" He had to remind himself that it's not his job to judge what others might find meaningful. As an exercise in empathy, he even forced himself to imagine what his own question to God would be.
"Will Whisper be a huge success?" I suggest, figuring that's what any startup founder would want to ask.
"No, no!" he responds. He's already confident enough to believe that Whisper will be big—or if he has any doubts, perhaps that's a secret he's decided is better kept to himself.
A sidebar on this story entitled "Generation Delete" was removed from this story by the editors due to several fact-checking errors.