Tiger Woods, doublethink and failed startups

The technology industry talks a lot about failure. Everyone has had a brush with it, and everybody likes to say it is an important part of success — though of course nobody really wants to fail. Most startup entrepreneurs wear the failed companies they’ve founded or worked for as a badge of honor: battle scars earned on the road to riches.

Not everybody thinks this is a good thing, however. Jason Fried of 37 Signals, for example, is certainly not a fan of the failcult:

I don’t understand the cultural fascination with failure being the source of great lessons to be learned. What did you learn? You learned what didn’t work. Now you won’t make the same mistake twice, but you’re just as likely to make a different mistake next time. You might know what won’t work, but you still don’t know what will work. That’s not much of a lesson.

And he’s right that there is an important perception gap here to worry about. After all, worshipping failure is only worthwhile if you assume that it is a precursor to success. Yet logic says that there are no guarantees that a person who fails once, twice or even three times is any more likely to strike gold on their next attempt. Sometimes you learn from your mistakes, sure. But sometimes people just aren’t good enough to make the cut.

What’s interesting to me about the industry attitude to failure, though, is the way it is spoken about all the time and yet rarely truthfully examined. While the Silicon Valley truism says “fail early, fail often” is often bandied about as a good thing, it’s actually surprisingly rare for people to talk openly and honestly about the details of getting it wrong. And considering the proportion of companies and ideas that have run into the wall, you might expect there to be a massive volume of people laying it all bare and talking about their mistakes.

That’s why I was so interested in three stories I came upon this week that dealt with failures in a way that was refreshing: openly, honestly, candidly.

‘Swallow your pride’

Justin Hall, used under Creative Commons license courtesy of Joi ItoFirst, Justin Hall published a long and detailed of the ups and downs of his online games company, GameLayers, which shut down in 2009. Justin, a web veteran, blogger and journalist, started his business around an intriguing idea: building a layer on top of the Web that turned your daily Internet consumption into a game. It’s what they called “passively multiplayer online gaming” — players would gain points for visiting certain sites, find treasure on one page or set trap for a rival on another.

Over the course of its life, the business raised $2 million from a mixture of angels and venture capital firms, but struggled to achieve success with initial idea. As things came to head, it made a last-ditch effort to save itself by switching to the rapidly expanding world of making Facebook games — but that only lasted for a short period before the company shut down altogether.

Justin’s account is a straight-shooting, sometimes tough, sometimes whimsical look at what it took to be CEO and where things went right and wrong. Among the problems: the idea required too much engineering, they realized they had sunk a lot of money into infrastructure costs, they got stuck on a few staffing problems and monetization wasn’t baked in enough. But in the end it was really an execution problem — the idea was fun, but it wasn’t fun enough, and nobody had the presence of mind or understanding to realize it.

Looking back I believe we needed to clear the decks, swallow our pride, and make something that was easier to have fun with, within the first few moments of interaction. That may have meant scrapping “passively multiplayer” as a game concept, or a toolbar as the mode of interaction. Those were pretty core to our initial business plan, so it took us a long time to see those concepts through to revenue failure.

His experiences chimed with another story I read earlier this week from Finnish entrepreneur Joakim Achren.

‘Never stop trying new things out’

Achren’s business, Ironstar, was also in games and followed a similar trajectory. The company shut down last month, and Achren published a short eulogy on his blog that bears a strong relation to. Like GameLayers, Ironstar began by making its own ambitious platform before switching to Facebook games — only to find that early success was hard to keep up.

“We can only blame ourselves for this, since we mostly focused on monetization first, retention second.” he lamented. “New features were aimed at paying users and less at the masses. Soon we had a game that didn’t monetize that well any more.”

‘Is it over yet?’

Then, still thinking of games, I came across this wonderful piece on Kotaku about the failure of a Facebook game called Cow Clicker. The game was designed by academic and games author Ian Bogost, who intended it to be a parody of the mindless grinding games that have proven so popular.

His brand of failure, it turns out, was to be too successful. Cow Clicker was meant to be a joke: instead it became something of a phenomenon. Thousands of people played, yet many of them did not understand that they were part of a joke. In the words of the article the game “developed an active player base — people who missed the humor and attached to it as if it were a “real” game.” And the more he tried to mess with them, the more they kept going.

What a sadistic version of success he had unleashed upon himself.

OK, here’s where Tiger Woods comes into it

I am not entirely sure what lessons other people can learn from these failures, especially since they seem so disparate. Yes, they all concern games — but the nature of their failures are very different. One was not monetized enough; another was monetized too much. Two of them didn’t get enough players, one of them got too many. It’s a muddle.

But whatever lessons you draw, these three tales struck me as honest discussions of failure in a world where we usually kid ourselves about it. We all hear about failure, but we don’t expect it to happen to us.

Perhaps there’s good reason for our self-deception though. Perhaps it’s a form of mental delusion we must have if we are ever going to really succeed.

This dual state is something that the British writer and former Olympian Matthew Syed refers to in his book Bounce as a version of Orwellian doublethink. In sport, he suggests, champions have to believe completely and utterly that they are going to succeed: that they will beat their rivals, that they will land that shot, that they will make that catch. And yet, they also know that failure is highly likely — and they have to be prepared to deal with it, because not everybody can win.

[top coach Timothy Gallwey] advises the golfer to associate a difficult putt with some action that has never failed, such as simply picking a ball out of the hole. “By vividly associating with this easy act, there is no room left in the mind to associate the upcoming putt with failure,” he writes.

But any sensible golfer — including Gallwey and, for that matter, Tiger Woods — must putt with caution; he must putt in such a way that, in the event of a miss, the ball rolls only a couple of feet past the hole, so that the next shot is a tap-in.

So what Gallwey is really saying is that a successful golfer must attempt to create subjective certainty in his own mind that he will make the putt, while simultaneously playing it at such a pace that acknowledges the possibility that he might miss; he must executive a shot that is certain to drop in a way that concedes the possibility of failure.

Startups are much the same. When we talk about failure, we visualize success. Anyone starting a company juggles these two things in their mind without ever necessarily acknowledging them. The same doublethink that made Tiger Woods a great golfer is precisely the sort of mental delusion that great entrepreneurs also have.

And even now, after reading all of this, I am not sure if that mindset is part of the magic, or part of the problem.