Ever tried. Ever failed. Fail again. Fail better. Growing old in Paris, the Irish writer Samuel Beckett could never have expected this fragment to become a tech industry mantra. But it has, and with good reason: The success of Silicon Valley is built on failure. This may be its greatest innovation. The region broke ahead of its rivals because it encouraged people to take big risks and did not punish them when those risks did not pay off.
At one level, this forgiving attitude reflected the influence of Bay Area hippies who shaped tech culture from the beginning. At another, it reflected the rise of new funding models. Early venture capitalists embraced risk rather than avoiding it; they expected most of the companies they invested in to fail. The failures did not matter, so long as the few that did succeed succeeded big.
The rise of software and, later, the web, made it possible to succeed at a whole new scale. This in turn enabled investors to tolerate more and bigger losses, because when the moonshot landed, the returns were astronomical. When you found the right product-market fit, you could eat the world, fast. In the meantime, with companies appearing and disappearing so quickly, people had an interest in staying friends, in sharing expertise, in going to Burning Man together.
Not everyone gets invited to the caravan, of course. To get funded, it still helps to be white, to be cis, to be male, to have been admitted to Stanford, and even completed a course or two, before dropping out to raise your Series A. While some people can only fail up, others fail out, and many never get a chance to try at all. It also helps to be young—or, as the saying goes, to “have a lot of runway.” Don’t trust anyone over thirty used to be a political slogan. Now it’s a business strategy.
Above all, to fail well, you must undertake a certain type of endeavor: A startup that could scale massively. A sandwich shop that fails was a bad idea. A sandwich delivery app that fails was a valuable learning experience for its founders; the market timing just wasn’t quite right. Struggling taxi companies are in terminal decline, but a ride-hailing app that loses two billion dollars per year is one of the most successful companies in the world.
This model of success may seem strange, when seen from Mars. But for the people to whom it is available, tolerance for failure is one of the best qualities of Silicon Valley. Letting people try things that might not work really does stimulate creativity. It fosters a respect for hard problems, and collaborating on those problems creates a sense of community. The course of true innovation never did run smooth.
If Silicon Valley is built on failure, it is also built on stories about failure. Once upon a time, a Reed College dropout got fired from the company he founded, then came back more than a decade later to invent the iPod and iPhone. A UCLA dropout started a company that declared bankruptcy to avoid lawsuits, started another company where he committed tax fraud, moved in with his parents to save money, moved to Thailand to save money, then came back and cofounded Uber.
Travis Kalanick told this story at FailCon, a one-day conference started in 2009 in San Francisco to teach startup founders to “learn from and prepare for failure, so they can iterate and grow fast.” Since then, it has become so common for entrepreneurs to talk about their failures in public and in long Medium posts that FailCon itself started failing to attract the audience it once did. So the founder has licensed the brand in “over a dozen cities on six continents.” You can attend FailCon in Ulaanbaatar. You can attend FailCon in Porto Alegre.
You go to learn the conventions of a genre. There are many ways to fail: go bankrupt, get acquired, get acqui-hired. To fail well, however, you have to get your story straight. A good founder story always describes failure without bitterness. It has been an incredible journey. I learned a ton. It presents every failure as temporary—a waystation to success.
Storytelling is not only for founders. It is a skill that everyone at a startup should cultivate, because the vast majority of startups will fail. And when you suddenly learn that you are out of work and all that equity you pulled all those all-nighters to earn is worthless, no job interviewer will want to hear that you got screwed over. They want to hear how you grew.
Even if you do get hired at one of the biggest tech companies, the risk of failure does not go away. On the contrary, a funny thing happens: the more successful the company becomes, the higher the bar for any internal project to be considered successful. If you build a startup that gets ten thousand users, you could sell that startup for seven figures. But once you work at a platform with billions of users, if you design a feature that only a few million use, your bosses will shake their heads and shut it down.
If something you spent years working on fails, you do not just need a story to tell your current or future employers; you need a story to tell yourself. You want to be able see those years as part of an incredible journey, too.
Silicon Valley tells itself one set of stories about failure. It has another story that it tells everyone else. Namely, that the old world has failed. The old world was analog: government bureaucrats, boring businesses, factory jobs, gray flannel suits. The new world is flexible, Technicolor, gymnastic, young. It has no dress code. It is neither white-collar nor blue-collar: it wears no collars at all.
In the new world, everyone will live a better life. This was the promise sold for decades by tech industry leaders and politicians alike: tech would drive American growth, creating widespread prosperity. This sounded good in an era of deindustrialization and spiraling inequality. It sounded even better after the 2008 financial crisis wiped out middle-class savings. As wages continued to flatline, the smartphone-driven gig economy would pick up the slack. Asia might be rising, but Silicon Valley still provided a bulwark of essentially American creativity; just look at all those Chinese nouveaux riches standing in line to buy the latest iPhone.
A set of political assumptions followed from these claims. The most important of these was that it was all right for a handful of former failures to accumulate vast amounts of money and power, so long as what was good for Silicon Valley was good for humanity. If tech was the future, why would anyone, or any regulation, want to stand in its way?
The government bought this; the media bought it; almost everyone seemed to like two-day delivery and the ability to chat and share pictures for free. It was not just in America. The Silicon Valley model was replicated all over their world. Yet, in the past year, the narrative has started to change.
Anyone paying attention knew that there were problems in the tech industry, and with its products. We knew about the systemic racism and sexism, the exploited gig workers and Silicon Valley service staff, the bots and the trolls and the fake news, the swarms of Pepes and incels. Now, since revelations about the role of disinformation on Facebook, Google, and Twitter during the 2016 election, criticism of Big Tech has reached a new and unprecedented level.
The Silicon Valley story has come down to earth. Maybe these companies are just companies after all. Maybe they are pursuing their self-interest as any capitalist firm would. Maybe, even if their IPOs occasionally toss some money to California state coffers shortchanged by Prop 13 (o hai, Snap!) the interests of tech companies do not perfectly align with the interests of humanity.
There are signs that the interests of tech leaders aren’t even perfectly aligned with those of most tech workers. After the 2016 election, many good people who entered the industry because they wanted to change the world were appalled to see their supposedly liberal bosses warming up to Trump. More recently, a wave of worker organizing within Google, Microsoft, and Amazon against collaboration with the Pentagon and ICE shows how big the rift could grow.
Burning Man could get awkward.
As scandal after scandal surfaces, Big Tech CEOs apologize for their mistakes. We will do better. Our AI will fix it. For many onlookers watching Mark Zuckerberg before Congress, (“We sell ads, Senator”) a troubling question began to emerge: What if the mechanisms that enabled advertisers to reach “Jew haters,” white supremacists to harass BLM activists, or far-right conspiracists to flood users’ feeds with disinformation were not, in fact, mistakes? What if Facebook is doing what it was designed to do?
The system may be working exactly as it is supposed to. If so, is the definition of success we have been using wrong? What if the success of Silicon Valley is failing most of us? This issue ventures a few possible answers to these questions. It explores what happens when technology blows up and breaks down. It looks at failures of code, institutions, narratives, and imagination. In so doing, it tries to imagine a better way to live with our machines—and to build new ones.
There is no shame in failing, until there is. Having been exempt from scrutiny for so long, many tech leaders seem genuinely stung by their first taste of criticism. Don’t they see? We’re working so hard. Taking a cue from Trump, some of them have take to Twitter to denounce their critics as liars, and to challenge the legitimacy of the media as a whole.
There has long been the sense in Silicon Valley that anyone who criticizes is simply a hater. We take the opposite view. Engaging with failure is, as FailCon could have taught us, the first step to growth. Only, that growth may have to happen in a different direction than Silicon Valley has been imagining. We may not need to iterate to grow faster but act boldly to create a more expansive and equitable world.
The only failure that should frighten us is not taking advantage of the opportunity that this moment presents. Complacency is no way to honor the disruptive potential of technology. To paraphrase one interview in the following pages: Criticism can be the highest form of love.