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My big fail: losers come clean on their all-time low

Succeed, and you want to tell the world. Fail, and no one wants to know. Winners turned losers, from presenter Piers Morgan to Olympic hopefuls, open up about their crash-and-burn moment.

Marc Hemeon, 39, was until recently a senior engineer at Google. Drinking a milkshake and twirling on a swivel chair at his home in Mountain View, California, he describes the app that was meant to make him rich. “Polling software. You swiped left to say ‘yes’ to a picture of something, right to say ‘no’.” Hemeon, a father of two, got the idea when he noticed his teenage daughter taking pictures of herself. This outfit, she’d ask her friends, texting them a photo: yay or nay? Hemeon called his app YayNay; it was “meant for 13-year-olds to use while shopping at Gap”.

He built it in six months, working with friends from Google. “My daughter loved it. Her friends loved it. And, of course, you have the audacious feeling that this is going to be a hit, the next Snapchat or Instagram.” A month after launch, YayNay had around 1,400 users and Hemeon was offered six-figure investment. As a Silicon Valley lifer, he was familiar with its rapacious acquisition market and could not help figure a few sums. “In terms of acquisition price, the thinking is that for every engineer you have, you get about $2m. YayNay had a team of four, so that’s $8m right there. Bump it up for the size of the audience, I don’t know, we probably could have sold for $10m, $15m…”

But then Hemeon noticed something. His software was meant to simplify an exchange that might take place, several times a day, between young people: “Do I look cute in this?” Regrettably, adults were able to join in that conversation, too. Hemeon learned that at least one of his 1,400 users was using YayNay to collect and curate photographs of half-dressed children. His own son was among those sent a message, through the app, proposing sex. “My initial reaction was embarrassment. Followed by panic. And then, maybe it’s a dad thing, I went into full-on freaking zombie-killing apocalypse mode.” 

Hemeon shut down the app. “Burned bridges with my engineers. Burned bridges with my community. And my sweet wife…” He had to explain to her that the thing he’d spent half a year inventing turned out to be a brilliant piece of paedophile tech. Moreover, one that had opened a direct line of communication between their son and a user who went by the name “boylover”.

This is Marc Hemeon’s story of failure and he tells it with TED-talk swagger: the narrative is tidy, the lessons harvested and brought out for study. (“Next time, in meetings, we’ll put our sexual predator hats on first.”) It is failure filtered the Silicon Valley way – as something nearly admirable, certainly confessable, an improving experience that may be dissected plainly and in public.

In the tech sector, there are several events that exist to showcase postmortems such as this. The most prominent is FailCon, a conference series that began in San Francisco and at which wounded entrepreneurs reveal their mistakes to an audience of ticket-holders. The event’s founder, Cassandra Phillipps, a 31-year-old Californian with purple hair, put on her first FailCon in 2009. In the years since, she’s watched what amounts to a failure boom take place in her industry. “Our goal was to make these conversations happen,” she says. “And in San Francisco they’re happening.”

Phillipps ascribes this mainly to the teachings of Eric Ries, an influential tech guru whose “lean startup” philosophy encourages failure’s embrace. (Ries argues, essentially, that young companies should rush towards mistakes in order to respond to them and improve.) Also significant, Phillipps says, has been the delicate economy. “That opened up a comfort, because none of us was doing great, in talking about what was going wrong. We couldn’t lie any more.” The tech world, Hemeon agrees, “is in the middle of a love affair with failure”.

Are the rest of us missing out on something?

***

Failure is universal in a way that success is not. A failure confessed tends to make somebody endearing, while their successes, told aloud, may make us want to bite them. And still it is success we dwell on. Search your social media newsfeeds for admissions of failure, and you’ll find them; but the success story, the achievement post, rules.

I became interested in failure having got up close to a good few success stories myself. As a writer, I’ve profiled people who have got somewhere close to where they want to be: high in the album charts, at a Cup final or in a CEO’s chair, front and centre in a Hollywood film. Research and retell the histories of enough achievers, and their rise begins to look less talent-fuelled – not so much the result of hard, solitary toil – and more like a bet that has paid off. The flourishing musician, the medal-winning sportsperson, the profitable entrepreneur: all of them took a punt, once, and we come to consider their story because that punt came good.

There’s another narrative we’ve become familiar with: failure as a past-tense business, something overcome. It’s a narrative that fuels a self-help industry, books titled Success Through Failure, How To Fail Most Successfully, How I Raised Myself From Failure, Fail Better, Fail Up and Failure: The Womb Of Success. But I wonder what there is to learn from the countless others we don’t hear about, those relative failures without whom there could be no corresponding successes. The people who simply fail.

What does failure feel like in the low, crummy moment of it? I speak to a couple of musicians, hopefuls who had high ambitions in rock or pop and for whatever reason had to shelve them. It is possible to get by as perfectly OK teachers, lawyers, chefs or journalists, but there are certain pursuits that seem to insist on binary dealings with success and failure, and the music industry is one.

“No magazine covers, no major label record deal, no tours, no sponsorships, no hit song, nothing,” says Will Jaeger, a Texan, summing up a 12-year effort trying to make it as a rock drummer. “I spent on gear what people spend on college educations.” Now 33, Jaeger was finally forced to stop performing with his band because he was experiencing terrible panic attacks, back there behind the drums. “I had wrapped all of my self-worth in a fantasy. And when I began to realise the fantasy wasn’t going to happen, my subconscious let me have it.”

For Kevin Yee, member of a once-promising boy band, failure felt like “the deepest punch in the gut”. Back in 2000, Yee’s group, Youth Asylum, were waiting to perform at President Clinton’s big, televised New Year celebration. They were cut from the running order at the last minute, and given the news while they waited in the wings. “We had our fancy outfits on and everything,” Yee says. “I still think about how my life would have been had I been able to take a few more steps.”

***

Last year, 270 people applied to speak at a FailCon event in the US. Cass Phillipps, organising, read through the submissions and considered each one carefully. Then she got in touch with about 260 applicants to say no, sorry, their failures were not quite bad enough. A failure can seem to redouble on itself like that. Stephen Rapoport, the 33-year-old organiser of Failboat, a London-based counterpart to FailCon, tells me he originally thought about staging one of his meetings on an actual boat, and would have done but for the vague superstition that the boat “would burst into flames and sink”.

Rapoport conceived of Failboat after a failure of his own: his peer-to-peer accommodation service, Crashpadder, was crushed by a rival, Airbnb, in 2012. In the weeks leading up to its closure, Rapoport found himself driving around late at night, “zigzagging London’s bridges back and forth, just to have something to occupy my mind that wasn’t painful”. He launched Failboat soon afterwards, a regular meeting at which battle-worn CEOs could come together and compare bruises, “almost as a form of group therapy”. It helped. “In politics, in business, in human relationships,” Rapoport says, “I can’t imagine anything being harmed by more openness and honesty about failure.”

Piers Morgan would agree, and tells me that, when it comes to failure, he has no time for squinty evasion. The British journalist and TV presenter, once the editor of the Daily Mirror, has lived in the US for years, where “I see it all the time,” he says, “people who refuse to accept, or talk about, or deal with any real setbacks in their lives. Especially here in Hollywood. The instinct is to constantly portray yourself as a fabulous success – everything sunny, happy, successful, wonderful!”

Morgan moved to Los Angeles in 2011, to front a primetime news programme on CNN. A huge gig, it ended last March, taken off air following low ratings. “Which played out as this catastrophic, horrendous, heinous moment in my life,” Morgan says. “It was as if the only thing left for me to do was stick my head into a large slab of sand and basically disappear from public life for at least 20 years, by way of penance.” Instead, he says, he spent some time in the garden of his Beverly Hills home. “And when I put it all together, I thought, ‘Well, if this is failure, then I’m reasonably relaxed about it.’” Morgan capped the thought by smoking a Montecristo No2 cigar.

He puts this resilience down to his “force-field of self-confidence. It probably helps that I went through the rough and tumble of running a daily newspaper in Britain for 10 years.” (Morgan was sacked as editor after publishing photographs of UK soldiers abusing Iraqi prisoners that turned out to be hoaxes.) “Not everyone has got my ability to just park these things to one side,” Morgan says. “I’m not trying for a moment to say, this is easy. It’s not, it’s difficult. Failure’s always a bummer. It’s how you deal with the bummer.”

Morgan has a suggestion. “Seethe. For 10 quiet seconds on your own. Then go and do something you enjoy.” As soon as he was fired from the Mirror, he says, he rushed home, opened a bottle of Puligny-Montrachet and ordered a Chinese takeaway. Thus armoured, he watched his professional obituaries play out on the evening news. “Highly recommended, dealing with setbacks via French wine and sweet-and-sour pork balls.”

***

While Piers Morgan suggests 10 seconds as the sensible amount of time to process and dismiss any feelings of failure, in New York I meet a man for whom it’s taken a little longer. Philip Schultz, a poet, sits down for breakfast with me in his small Manhattan apartment: kitchenette, facing sofas, desk. On his shelves are hardback copies of his 2007 collection, Failure, a winner of the Pulitzer prize. “Failure has been the great theme of my life, I think,” says Schultz, who has just turned 70. “But it took me until I was in my early 60s to be able to deal with it.”

The sad, lovely poem that gives his award-winning collection its name is about his father, a shambling and inexpert businessman who several times bankrupted the family when Schultz was young. In a bleakly funny sequence, the poem ticks off some of his father’s blockbuster catastrophes: “a parking lot that raised geese/a motel that raffled honeymoons/a bowling alley with roving mariachis”. It wasn’t so funny at the time, Schultz says. “My father was going to fail no matter what, because even when he was successful, he couldn’t appreciate it. He was always lost in thought, dreaming. His lips were moving, planning the next step – there was no moment.”

This, Schultz thinks, was because of his father’s mother, a woman who brought her Jewish family to New York away from Russia’s pogroms. “They came here having faced death on a regular basis. She saw life as either/or. You succeed or you die. Nothing in between.”

We happen to meet in a good week, an important week; this morning Schultz is almost ecstatic. At the age of 70, he has had an epiphany of sorts, watching the news on TV. “These two climbers, they climbed the hardest mountain in Yosemite in California. Straight up. It took them 19 days – their hands were all torn up. One guy didn’t have a voice from screaming, and they were both being interviewed at the top, and obviously the interviewer was after a sense of victory, of success. ‘You’ve done something no one else has done, how do you feel?’ They looked nonplussed. I mean, they looked confused. There was an incipient pride, of course, but they looked like… All they wanted to talk about was the 19 days. The 19 days of endless hours with torn hands, freezing, sleeping while still holding on with their fingertips. And suddenly they’re on a ledge and everyone is there opening champagne, and they’re supposed to accept that this is what they’ve always wanted? That they always wanted this success?”

Schultz looks at me, delighted. “They wanted the 19 days on the mountain.” Success, failure, he says, “are almost artificial. People fall into the way of thinking that there’s one or the other, it’s black or white, that there’s no in between. Of course, we all live in between.” Happiness, he thinks, is in between.

The poet eats a pastry and takes up his coffee. He tells me he only wishes he’d figured it out sooner. He remembers winning the Pulitzer for poetry back in 2008, and how even as he received the award, this awesome signifier of achievement, he felt the moment-ruining pall of failure. Because, really, he thought then, hadn’t he always secretly wanted to be a novelist?

***

Cass Phillipps, founder of FailCon, has for some time hoped to run her conference in the UK. To that end, she enlisted a British businessman to form a team and get it started. But FailCon London, well, it failed. Key people dropped out, others didn’t turn up. It might still happen, but Phillipps sounds exasperated when I ask about it. “It keeps falling apart.”

She has spent six years of her life considering other people’s failures – the comical, the instructive, the upsetting. “And sometimes I wished I was close enough to people to say, ‘Man, your life would be easier if you accept you’re not an entrepreneur.’” She’s come to understand that “a failure isn’t always big. It might just be a realisation that you could be doing better things with your life.”

When I ask her to tell me about her own failures, she says, “I actually consider FailCon to be a type of failure. It had a lot more potential to grow than I ever gave it credit for. By the time I realised its potential, I had already kind of gotten tired of the stress that it was bringing to my life.” Several times, Phillipps says, she’s had to explain to distressed applicants that she’s not a therapist, nor a psychiatrist. “I’m an event planner!” Meanwhile, the FailCons she once staged in her home town of San Francisco have been discontinued. “Failure’s so talked about here right now that having an entire event about it is actually less of a market fit.”

When Phillipps first started out, she had a hope that, “by talking about failure, we’d make it easier to cope with”. She thought that failure could be softened, sweetened, made somehow less painful. “But six years of being the producer of FailCon,” she says, “and I still think failure hurts like a bitch.”

(인용: Tom Lamont, 가디언)