“Fail Fast, Fail Often” Is a Great Motto for Running a Business. It’s a Terrible One for Founders.

Justin Wolske
In Media Res
Published in
6 min readDec 21, 2017
“‘Tis merely a scratch, failure!”

There is a fetishized schizophrenia about failure in the startup world. On one hand, it’s really bad form to talk about. Gossip of missed milestones or bad team dynamics can hurt valuation. Past mistakes can give investors — who are usually looking for a way to get to “no” anyway — an out. Losing has a stench that sticks to people, whether you’re talking about sports, politics or business. No one wants to be around it. Obviously.

But in the tech world, there’s another very popular way of looking at failure. The way really rich VCs and founders talk about their failures in that self-deprecating way to make them seem more down-to-earth. Failure is a tonic, a spinach that one has to eat in order to earn whatever successes come afterward. It is part of the Hero’s Journey, the necessary slog that makes the inevitable victory at the end that much sweeter. The concept of failure has been codified into the DNA of the modern startup lifestyle.

“Fail fast, fail often.”

It’s a clever phrase, attached to the lean startup methods of quick iteration, rapid protoyping, agile development and generally treating product development more as a scientific experiment than some mystical, gut-driven process. Once one hears it or repeats it, one feels as if they have just injected more wisdom into whatever situation one is in. It’s a helpful talisman to push you into action. There are two problems with it, however.

The first is that it conjures a weird idea of what failure is. Being wrong or even missing a milestone or a quarter is not failing, not in any useful sense. A pro baseball player who hits .400 in a season would certainly be the man to beat for MVP, if not in the fast lane to Cooperstown. Is the .600 worth of outs failure? Is a scrapped prototype that is cleared for a more effective design a failure? I don’t know…maybe. Maybe it’s just semantic games. But a lot of the “fail fast” ethos seems to revolve around the basic experimentation and iteration that goes on in any chemistry or physics lab in the world. I don’t think they call their dud experiments “failures.”

The second problem is a little more important. Almost ten years ago, I was producing for a German-Hong Kong film studio in Cebu, Philippines. It was an absurd place, with American film student interns and Russian models running around the place for no apparent reason, while Filipinos actually ran things. Nothing was ever really filmed, but great sets were built and much San Mig was consumed. Every day, I looked out of my office upon the stunning Pacific Ocean. Just of frame of this picture sat a shack on rocky shore. A fisherman and his large family lived there. When the tide pulled way back in the afternoon, the whole family would come out quickly, scooping up crabs, shellfish and whatever sea life they could bring to market. They were methodical and fast, the children’s feet already immune to the sharp rocks. When the tide was in, the kids would be 40 feet up in the coconut trees, racing each other to drop as many fruits down to their teammates below. As a producer with nothing to really produce, I would chill with the models by the pool, and we would cheer them on. There was no one there to kick us in the face, which would have been appropriate response.

There is no such thing as waiting in line in some government office for a benefits check in Cebu. That doesn’t exist. There are industries like tourism, shipping, and heavy industry, but stable employment is scarce, and the Cebuano exports of gorgeous furniture or guitars are hard crafts to master. As such, you can’t throw a rock without hitting a boot-strapping entrepreneur. They bring goods to market. They drive their jeepneys for 14-hour shifts. They can get you a good gun for cheap (like Americans, Filipinos love guns). My point is, I challenge you to shrug your shoulders and say “Failfastfailoften, brah!” to a Filipino fisherman with five children. It’s as absurd as watching a movie crew get drunk in the middle of the day atop a coconut tree. The stakes are too high for such a cavalier attutude. You don’t pivot out of poverty.

And it doesn’t have to be thousands of miles away, either. This laissez-faire relationship to failure would be just as bizarre to a taxi driver in New York or a general contractor in Western Arkansas. Because failure is missed mortgage payments and bankruptcy. Failure is some high-stake ish. Only in an environment of Stanford grads and trust funds could a group of founders and investors codify failure to be as light as a growing pain. How does an entrepreneur who’s risked everything square this concept of disposable failure with what s/he is doing? It’s hard; it’s makes the mecca of modern American entrepreneurship — Silicon Valley — seem so alien to so many. It also speaks to the young minds of the mostly male, mostly white technologists who populate the species. Young men who have access to many opportunities after this current one, who don’t want to grapple with the emotions that leak out after real, deep failure, the existential terror that can result. Young men who don’t want to be seen as weak or wanting.

So we make this silent handshake with each other: let’s move the goalposts and call these other things “failure.” We can have little ones all the time, we can move past them, we can treat them as due diligence on the way to a $50M valuation. And it’s frustrating because, there is a lot in the lean method of experimentation that is valuable. Testing hypotheses is very useful. A/B testing is a worthwhile thing to do. “Get out of the building!” is some of the best, earliest advice a young entrepreneur can hear. This process of experimentation is a good counterbalance to the preciousness that founders often have about their ideas. It’s a way to isolate what is working and what is not. It’s critical to expose entrepreneurs — especially young people — to disappointment, so they can bounce back stronger (and to be fair, even originators like Eric Ries push back on the way failure is viewed in the lean method).

So it’s a great thing to increase efficiency and build grit and operate scientifically. But know this. When you fail, for real, it will hurt. Deeply. To the core. It may throw you into the depths of despair. It may ruin you. That’s what happens when you go for anything 100%, and no book by any thought leader you pick up at the airport will change that. That’s why I feel that the “fail fast, fail often” mantra is a very helpful guide to apply to a venture, and a very harmful one to breathe in and live. The failure that is bandied about in the Bay Area and Boston is more about managing risk or evaluating progress. If you’re going to live this life, you’re going to have to be vulnerable to the prospect — the probability — of significant loss. But exposing yourself to those real stakes, and those real feelings, will inevitably make you a better founder.

Have an outstanding last few days of 2017. We’ll see you in January.

Justin Wolske is happy to talk about his failures in that really charming, self-deprecating way described above. He’ll get more real about them at GRID110 and Caseworx. You should join us.

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Justin Wolske
In Media Res

Justin is a film producer, entrepreneur and educator. He runs Caseworx, co-founded GRID110 and teaches at Cal State LA. He lives in Long Beach, CA.