The #fumblebrag Chronicles

In frothy Silicon Valley, stories about failure are a form of social currency

Caleb Garling
Published in
7 min readMar 26, 2015


Hi, I’m Caleb. I’ve fucked up. Let me tell you how I fucked up. And then let’s talk about it.

I’d been working on a web app that lets users publish graphics. Two weeks ago I’d found out that the app was going to be on Product Hunt, a site that surfaces cool products for tech fans. The problem was that we weren’t sure if we could handle the traffic, so my partner and I scrambled to find an engineer who could help us scale before going live. After a quick search, we found X, which is what I’m calling this person because it would be unfair to use X’s real name.

According to X’s resume — presented as a Google doc — X had been scaling applications for 15 years. X said that they worked for a large media company. X would work for almost no money, as X took side projects like this for the experience. X could start immediately. But X, who lived in San Francisco, happened to be in Nevada on vacation, so we couldn’t meet in person. X signed a work agreement with an illegible squiggle, and off we went.

See any red flags?

Twenty-four hours later, after working with X, my partner and I returned from dinner to find nothing working. This wasn’t *click* the browser is thinking, and thiiiiinking, aaaaaaand no, sorry! 404. This was click-not-found. Nothing tried to load. We weren’t down. We were dead.

X wasn’t responding to messages. I felt the grim reaper clasp my neck. My partner, the technical lead, started reviewing code and logs.

“Why…why would it do that?”

“Deny? The fuck is happening here.”

We were supposed to be on Product Hunt in 24 hours, and we literally had no product. I flashed back to a lunch I’d had with Mat Honan the same day of his infamous hacking that ended up a Wired cover story. And all I could think about in this moment was, Holy fuck, this is part two, except Caleb is a huge fucking idiot in this version. I gave someone with zero paper trail access to our servers, and they just steamrolled us for the LULZ.

Turns out, X had just made a mistake. X had uploaded the wrong config file. In case you don’t code: the config file contains the settings for how a computer should handle the code. It’s the instruction manual. One wrong tweak can kill an app. The entire wrong file? As my partner later put it, “You handle the config file with three white gloves.”

We fixed the problem. Nine months of work hadn’t been hacked to pieces. Everything was going to be fine. But I still had to take a walk and collect myself. I was responsible for running this project, and I’d allowed someone whose credentials were typed into a Google doc access to the nerve center of our app. It didn’t matter whether X was high-fiving on 4Chan or being absentminded. I’d fucked up. Simple as that.

Okay, let’s pause here. There’s something vaguely obnoxious about my story, right? First, when someone says they “fucked up”, you expect something far worse than a business gaff. But then there’s the pressure-cooker narrative. The buck stops with me, and so on. If the stakes weren’t so high, nobody would care. But since I’m so important that one mistake could derail the entire project, what I’m really saying is that I’m actually pretty awesome.

Welcome to the era of the #fumblebrag.

The idea that you can only succeed if first you fail captivates Silicon Valley. The mantra “fail fast, fail often” is recited around the Bay Area with the regularity that priests say, “Glory be to god.” Dropbox CEO Drew Houston is often quoted as saying, “Don’t worry about failure. You only have to be right once.”

And so a cottage industry has bubbled up around failing. This October FailCon, a conference on the topic that has spread as far as India and France, will convene in San Francisco again. Past speakers include Uber CEO Travis Kalanick, super-investor Vinod Khosla and Eric Ries, author of that Silicon Valley bible, The Lean Startup.

A younger, less grand event called FuckUp Nights started in Mexico in 2012, spread to over 90 cities around the world and has likewise struck a chord in the Bay Area. Entrepreneurs take the stage and fess up about past business blunders. On the fumblebrag spectrum, fucking up is failure’s less prestigious younger sibling. Failure implies you could have been great — you just didn’t get it quite right. When you fuck up, you’re just an idiot.

So a few weeks ago, my own fuck up just a week out, I attended a FuckUp Night at a place called StartupHouse near the Tenderloin. The event was so packed that the organizers had to turn people away at the door.

I listened as three speakers tried — and failed — to admit anything that sounded like actually fucking up. The first was a mobile games developer who mostly boasted about how his company had adjusted to a fast-changing market. The second was a photographer who made halfhearted attempts at explaining how his career had interfered with important moments in his life, but he was really there to recruit people for a photo series. The third speaker came the closest to telling a tale of actual fucking up — his agency took on a complicated account that sunk the company — but his story was so littered with lines such as, “It was a total masturbatory fest of me being a wannabe genius,” that it was hard to believe he had learned much from his mistakes. (It seems the organizers fucked up, too.)

When I asked people in the audience about their own fuck ups, most of them blushed or brushed off the question. Others would only disclose them off the record. People who had endured the grind seemed to want to hear about other people’s mistakes, not recount their own.

Why is it so hard to admit true failure and maintain eye contact? Part of it is that people tend to want a happy ending. Don’t be a bummer. Starting any business is hard, and a tech company is no exception, even if investment dollars seem to bubble out of Bay Area storm drains. FuckUp Nights and its ilk are a form of therapy. No one wants the presenter to say, “So now I live with my parents,” and drop the mic.

One fellow did tell me he’d finally shuttered his company after years of trying to make it. “We just never had that magic moment,” he said. Another shared that he’d once hired a team of engineers in Bangalore — 12.5 hours ahead of San Francisco — which meant he worked 24 hours a day for a while.

What it comes down to is that fuck ups and failures are evidence that you’re trying. You are out there. You are making things happen and you’re taking your lumps along the way — this is admirable. And hey, look at Kalanick and Houston with their faces on magazine covers. But the truth is that the odds are stacked against you launching the next Uber or Dropbox.

The fumblebrag narrative is built on the pious belief that every mistake gets you closer to success, that every No gets you closer to a Yes. Events like FuckUp Nights and Failcon exist because in the back of everyone’s mind lurks the worry that when you tally up your failures and fuck ups, those times you got back on the horse, those times you tried, tried again, those times you failed often and fast, you still might have nothing to show for it.

You could have been climbing real mountains.

During the 90 minutes I thought X had hacked us to pieces I found myself reflecting on what I’d do if our hard work had gone down the tubes. With proper safeguards you can’t really delete a web app, so this was fairly improbable. But the question still came to mind. Would I do the last nine months over again? Would I spend cycles talking to people in coffee shops, hashing out features and designs with my partner, researching media trends, whiteboarding interfaces, asking questions, asking favors, being told No, being told nothing, all to get to this same spot again — and make a better decision, having now learned from my fuck up?

I’d like to think so.

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