Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley

by Antonio García Martínez

The first sign of trouble was an externally visible one, a symptom that any suitably experienced startup practitioner could have detected: nobody from the early days of the company was still around other than Murthy. Every other single cofounder or early employee had left. As Vonnegut wrote in Bluebeard, never trust the survivor of a massacre until you know what he did to survive. And indeed in this case, Murthy wasn’t a mere survivor, but rather an author of said massacre.

Discreet inquiries on CrunchBase or LinkedIn, or emails to professional connections, tell the real tale.* Don’t work for the survivors or architects of massacres. You’ll live just long enough to regret it.

In the same way that a trust fund just makes a drug addict’s spiral more long lasting and painful, a cash-generating business that doesn’t improve the product postpones the inevitable by floating the charade, all the while actually making failure more likely. This strategy can work as far as keeping a company afloat while it’s working out the kinks in its core program, but it’s tricky, and it requires absolute management discipline to not lose focus on the product the company was created to perfect.

Here’s the lesson: when the company’s employee retention strategy is cultivating Stockholm syndrome, you’re in the wrong company.

Like the canniest early-stage investors, YC cared a lot more about the team at this point than whatever improbable idea we might have. The latter was really there only to judge the former; it was valueless in itself. Don’t believe me? Think your idea is worth something? Go and try to sell it, and see what sort of price you’ll get for it. Ideas without implementation, or without an exceptional team to implement them, are like assholes and opinions: everyone’s got one. Incidentally, the fastest way you can indicate your level of startup naïveté to a VC (or to anybody in tech), is either by claiming you’re in “stealth”—that is, with an idea so secretly valuable you can’t disclose it—or by forcing someone to sign a nondisclosure agreement before you even discuss it. You may as well tattoo LOSER on your forehead instead, to save everyone the trouble. To quote one Valley sage, if your idea is any good, it won’t get stolen, you’ll have to jam it down people’s throats instead.

Here’s some startup pedagogy for you: When confronted with any startup idea, ask yourself one simple question: How many miracles have to happen for this to succeed? If the answer is zero, you’re not looking at a startup, you’re just dealing with a regular business like a laundry or a trucking business. All you need is capital and minimal execution, and assuming a two-way market, you’ll make some profit. To be a startup, miracles need to happen. But a precise number of miracles.

Here’s more startup advice: if the drama around your departure from a startup recalls that of a former East German trying to jump the Wall, or Cubans hijacking airliners to Miami, then you should be as ecstatic at leaving as that same East German or Cuban.

People go into startups thinking that the technical problems are the challenges. In practice, the technical stuff is easy, unless you’re incompetent or really at the hairy edge of human knowledge—for example, putting a man on Mars. No, every real problem in startups is a people problem, and as such they’re the hardest to solve, as they often don’t have a real solution, much less a ready software fix.

Here is a key insight for any startup: You may think yourself a puny midget among giants when you stride out into a marketplace, and suddenly confront such a giant via litigation or direct competition. But the reality is that larger companies often have much more to fear from you than you from them.

To quote Balzac, “The secret of great fortunes without apparent cause is a forgotten crime, as the crime was properly done.”

The harsh reality is this: to have influence in the world, you need to be willing and able to reward your friends and punish your enemies.

“You could parachute him into an island full of cannibals and come back in five years and he’d be the king.”

In my limited experience, there are two traits that distinguish successful startup founders at whatever level of the game, from the forgettably minuscule (e.g., AdGrok) to the epoch changing (e.g., SpaceX). First, the ability to monomaniacally and obsessively focus on one thing and one thing only, at the expense of everything else in life. I lived, breathed, and shat AdGrok. Thanks to focusing on AdGrok, I watched my daughter grow up through the frame of a Skype window while I was in AdGrok’s Mountain View shit hole. I had no social life outside of schmooze-and-booze tech events, at which I would wear my AdGrok T-shirt and engage in techno small talk with people I didn’t really care about. I had no hobbies or outside activities of any kind, except very occasional trips to the gym. My sailboat, into which I had poured two years of money and weekends to restore, slowly rotted in the sun. I never read anything except the tech press. Movies were out of the question. The ladies? While I was nominally still in a relationship with British Trader, my penis was anatomically equivalent to my coccyx: a purposeless vestige of a bygone era. Second, the ability to take and endure endless amounts of shit. I was raised under the sadistic care of a sister ten years my senior who delighted in unleashing endless taunts and abuses. My father was a domineering man, in every way. I spent years in an all-boys Catholic school filled with brutish bullies and cold, aloof priests. We did nothing but...

The entire SF startup world, in case you haven’t been keeping track of the geography, lives between First and Eighth Streets, and between King and Market Streets, in SF’s SoMa. A former bombed-out industrial space, dotted with a few flophouses and taken over by addicts until the late nineties, it was the eight-by-eight-block playing field of global technology.

As every new arrival in California comes to learn, that superficially sunny “Hi!” they get from everybody is really, “Fuck you, I don’t care.” It cuts both ways, though. They won’t hold it against you if you’re a no-show at their wedding, and they’ll step right over a homeless person on their way to a mindfulness yoga class.

The dev team is the engine of a tech company. If they were done, then we were dead in the water. If that engine couldn’t be fixed back into productivity, then it was time to sell the company while we even could.

Like every other engineer, despite my also being a product manager, I’d need to go through the engineering boot camp, the six-week course that ingested you a n00b and output you a Facebook engineer.* It was also a weeding mechanism that provided management with the first flag on potentially bad hires. Via accelerated courses in front-end code, back-end infrastructure, and everything in between, we learned the Facebook way.

As PM, if you can convince engineers to build things you stipulate, you are golden. But if you can’t, then you are like the dictator who has lost control of his army. It doesn’t matter if you have the United Nations or the church on your side (i.e., if management has anointed you as leader), you’re ending up in front of a firing squad sooner rather than later. The most pitiful sight in the Facebook Ads team was the PMs who had lost the confidence of their engineers. Nominally in charge of some product area, they were like the government in exile of some occupied nation: sitting there with all the pomp of their position, sending emails and road maps hither and yon, and yet producing nothing.

A sharp contrast developed between Googlers working side by side. While one was looking at local movie times on his monitor, the other was booking a flight to Belize for the weekend. How was the conversation Monday morning going to sound now?

There are only two inflection points in personal wealth, two points where your life really changes. One is the aforementioned fuck-you money, the other is the even loftier fuck-the-world money. Before that first rung of fuck-you money, when you’re counting your nickels and dimes and shares and bonuses and what all to get to a few hundred K of dosh, all that changes is what I’ll call your indifference threshold to expense. If before you didn’t think about dropping $6 for another pint of beer with your friends (and believe me, I’ve lived through times when I had to think about even that), now you don’t think about the pricey $60 salmon lunch at Anchor & Hope. If previously you thought before indulging yourself with some questionably useful $50 gadget, now you’ll drop $500 on a new phone or ultracompact projector without thinking about it. As if you lived in some dodgy country undergoing a period of hyperinflation, what used to be worth $10 in mental decision cost now takes $100 to trigger. It’s like your mental decimal point of concern has moved over a zero (or perhaps more than one). You’re not even really thinking about costs until you’ve broken $1,000.

inside every cynic lives a heartbroken idealist.

It’s because you are without a doubt the least daring and least innovative person at your organization, because in the opportunity-rich environment in which you live, the ambitious and capable have left to pursue it. There’s a negative selection in which the cream (or whatever it is that initially rises) gets constantly skimmed off, and you are what’s left after years of continual skimming. Changing from big company A to big company B is cosmetic, as it’s of course at least a lateral move if not a step up. You learn that what matters in a big company is to avoid falling victim to firing or layoffs, and to appear important and critical to the company’s mission. You have mastered the art of “managing up”: namely, controlling the feelings and perceptions of the management layer above you. You take feedback well, and make sure to be seen speedily acting on that feedback. If you have reports, you champion their careers internally (make sure they know you’re doing that), and try to mold them into people like yourself, who are organizationally effective and recognized as such. In all but the most pathological organizations, your reports’ success will reflect well on you and create your own success. You make sure to form allegiances and friendships with your peer managers, particularly in organizations like sales or business development that you’ll need to push your business agenda forward. When there’s an ineffective and incompetent member in the organization, rather than calling...

Commuting was for the little people.

Always show enough skin to get a second date. If in doubt, show more.