Tripping on a Whisper

Michael Heyward isn’t cool, calm, or collected. And I like it that way.

The animated Michael Heyward you saw take on Michael Arrington (and lose?) today at TechCrunch Disrupt is the real deal. He’s empathetic, emotional, and, yes, defensive.

But that’s OK — at least in my book. I’m kind of over his Silicon Valley counterparts who spout off aphorisms they don’t believe and duck every question worth asking.

For those in the dark, Michael Heyward is the CEO of 2-year-old Whisper, a smartphone app for your candid confessions. Today, on stage in front of his peers, Michael lost his cool. He got overly defensive when Arrington challenged Whisper’s mission of making the world a more empathetic place. Arrington’s ammo? A Whisper post alleging that Gwyneth Paltrow cheated on her then-husband Chris Martin.

With a photo of the smiling, accused Gwyneth smiling down from the big screen, Heyward seemed to unravel in his responses. He stumbled through follow-up questions, got visibly agitated, and finally insisted that he have a moment to speak his piece.

Arrington’s challenge is a reasonable one, but Michael got lost in trying to defend his company’s approach to avoiding censorship while also preserving safety. He was tripped up, intentionally or otherwise.

Michael may have gone off track, but at the very least, I hope people will judge his behavior as indicative of a passionate man defending the thing that he loves.

Because that’s exactly who he is.

I met him in person late last year. I showed up and expected to get a lot of manufactured garbley-gook. Instead, I got several hours of his undivided attention and honest answers to occasionally unpleasant questions. I walked away thinking that this 20-something CEO (26 to be exact) was on to something big and important, and that he was refreshingly frank (just like his app).

I originally went to Whisper with the intention of writing a feature story on the boys’ club of Los Angeles, with special emphasis on youngsters like Heyward, Snapchat’s Evan Spiegel and Bobby Murphy, and Tinder co-founders Sean Rad and Justin Mateen. Michael changed my mind; he inadvertently convinced me that Whisper was a story worth writing. I think I made the right call.

Michael really likes this door, which alludes to the Harry Potter series. Photo credit: me. 12/12/2013

That’s not to say I love Whisper. I don’t regularly use the app, though I find it exponentially more uplifting than Secret, which makes me sad for society.

Here’s how I originally characterized Whisper (for CNET):

In many ways, Whisper is a reaction to the over-embellished existences we find on Facebook, Instagram, and Twitter, making it often moody and melancholy — and real in the most unsettling of ways.

It’s not for me but teenagers are eating it up.

Michael has created a space for them to remove the mask of perfection. And, more than anything, he genuinely, like actually, cares about the well-being of the kids that use his app. Hence the histrionics in the interview.

During our own meeting and calls, Michael got defensive with me too. And I’m pretty sure he hated some of what I wrote about him. Nature of the job. But I never doubted his sincerity — at least not after I decided he was being sincere. I went into our first conversation a cynical reporter, of course.

Roll your eyes all you want, but this guy wants to change the world so that kids can grow up knowing that their struggles are shared by others. Michael may have shown his youth today, but maybe his youth is an asset.

I’ll leave you with the (biased) words of Lightspeed partner Jeremy Liew, a Whisper investor, whom I spoke to when I was researching my story on Heyward.

“He and Evan [Spiegel] share this really innate, deep understanding of the user and the problem that the user is trying to solve.”

Clearly, the problems of adolescent users revolve around the taming of rampant emotions. If it takes one to know one, then I say to Mr. Heyward: bring on the emotions.