Takeaways from Chaos Monkeys by Antonio Garcia Martinez

I just finished Antonio García Martínez’s excellent memoir Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley, and it might be the best book I’ve read this year.

The author mixes juicy personal anecdotes with telltale corporate exposes, all held together with a gripping, true narrative and interspersed with historical quotes about the human condition.

Antonio has had quite the life, from quant at Goldman Sachs, to founding a YC backed ad tech startup that survived an IP lawsuit to be acquired by Twitter, to negotiating that deal so that he could go to Facebook instead, where he was eventually fired due to internal politics, and now he lives on a sailboat in the Pacific Northwest.

It’s a hell of a story, and he’s got the writing chops to tell it. I laughed out loud so many times while reading that my girlfriend decided to pick it up too.

My only gripe is Antonio himself, as the cynical witty outsider who expertly demolishes everything you hold dear without offering anything to replace it with.

He rails against capitalistic greed all while bemoaning how much money he needs to give his 3 children (all had with women he barely knew) a life of privilege. Then he rails against Facebook’s idealistic philosophy as built on wishes and half-truths. So money is bad, and idealism is bad — what’s left?

After reading, Antonio reminded me of people I’ve met who are too smart for their own good — who can see past the bullshit but haven’t replaced it with anything, so they just party hard and talk down your dreams. I’d love to grab a beer with him, but I’m not sure he’s someone I’d trust.

Here, I’ll share some of my favorite passages from the book, grouped around the following themes. You’ll:

  • Learn How to Navigate Corporate Politics,
  • Muse on nuggets from the History of Philosophy
  • Devour Startup Founder Advice
  • Smirk at Antonio’s Devilishly Snarky Opinions,
  • View Silicon Valley through The Eyes of a Cynic

How to Navigate Corporate Politics

I have no desire to work for a big company, so I found Antonio’s tales from the heart of the beast fascinating. Let’s ask him:

How do important organization decisions get made?

…gut feel, the residue of whatever historical politics were in play, and the ability to cater persuasive messages to people either busy, impatient, or uninterested (or all three).

What’s it like being a product manager?

It means fronting for the product in high-level meetings with senior management, and trying to place it, like a quickly falling Tetris piece, into the rudimentary blueprint of their world.

And perhaps most poignantly, here’s what I call his:

Elegy To The Middle Manager

You’ve seen excellent engineers and product people come and go, as your recruiters land the best new grads from every leading school. Your privileged position inside a powerful and market-leading organization exposes you to every industry trend and player, and pads your network with a roster of power and influence. Your ability to make any company’s senior management appear and deliver fawning and revealing product demos means you know everything that’s going on in your industry, down to the color of the clickable buttons in the products.
And yet there you are, lips bolted like pipe flanges onto some bigwig’s ass, plodding along like an ox yoked to a grain mill, grinding the grist the big-company machine requires.
Why is that? I’ll tell you why. 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 them an idiot to their face and firing them if possible, you channel feedback to their manager and learn to work around their incompetence. If the incompetence does not directly affect you or your team, you look the other way and focus on the levers you do control.
You’re middle management: you’re the necessary layer between the visionaries and risk-takers who created the organization, and the new acolytes of your religion for whom this is a job, and you are their first whiff of corporate culture and authority.

Yikes. Doesn’t sound very appealing, does it?

Nuggets from Historical Philosophy

Antonio is subtly well-read, weaving cultural anecdotes from his own heritage together with street smarts and bits of world history. These nuggets are thoroughly interspersed at choice moments in the text, but here are some of my favorites:

Antonio’s 10 Commandments:

  • Truth in the world resides only in mathematical proofs and physics labs. Everywhere else, it’s really a matter of opinion, and if it manages to become group opinion, it’s undeservedly crowned as capital-T Truth. And so you need to determine whatever the local version of truth is you’re inhabiting.
  • The Prince: war is never avoided; it’s only postponed to someone’s advantage.
  • 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.
  • Inside every cynic lives a heartbroken idealist.
  • Always show enough skin to get a second date. If in doubt, show more.
  • As they say, the ideal deal is one where both parties walk away feeling slightly screwed.
  • As the hardened SoMa veteran joke goes: the homeless have Android phones, while the techies have iPhones.
  • To paraphrase Lord Palmerston about great nations, companies like Facebook had no eternal allies and no perpetual enemies, they merely had eternal and perpetual interests.
  • It’s not the rats who first abandon a sinking ship. It’s the crew members who know how to swim…As Vonnegut wrote in Bluebeard, never trust the survivor of a massacre until you know what he did to survive.
  • Geoff Ralston, a YC partner, told us: people don’t really change, they just become better actors.

Also, have you ever heard of a dragoman? They were the official translators between Europe and the Ottoman Empire, but apparently were known for strategic mistranslations.

Mistranslation at work: the intentional kind that serves as diplomatic lubricant to get a deal done, and the more serious kind, which leaves each side thinking it agreed to a different thing. The Silicon Valley world is an almost perfect analogue, and we have deal dragomans of our own.

Startup Founder Advice

Everyone loves founder advice, and Antonio delivers in spades. Let’s ask:

How should I negotiate?

I you want to be a startup entrepreneur, get used to negotiating from positions of weakness.

What do I need to do to make my startup successful?

To be a startup, miracles need to happen. But a precise number of miracles.
Most successful startups depend on one miracle only.
For Airbnb, it was getting people to let strangers into their spare bedrooms and weekend cottages. This was a user-behavior miracle. For Google, it was creating an exponentially better search service than anything that had existed to date. This was a technical miracle. For Uber or Instacart, it was getting people to book and pay for real-world services via websites or phones. This was a consumer-workflow miracle. For Slack, it was getting people to work like they formerly chatted with their girlfriends. This is a business-workflow miracle.

What’s the hardest part of a startup?

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.

What should I do as the CEO?

Startups are experiments in group psychology. As CEO, you’re both the therapist leader, and the patient most in need of therapy. So what you do as a CEO is internalize that stress for the company and let it consume you instead of the rest.

Antonio’s Devilishly Snarky Opinions

Antonio is at his finest when he’s applying his devastating wit toward bashing things, whether it’s his ex-founder or capitalism itself. Let’s ask:

How do acqui-hires work?

It’s like the intentional mixing of refined European breeds with wild dingoes in Australia that produced the smart and rangy Australian cattle dog.

What’s the difference between Capitalism and Communism?

At their extremes, capitalism and communism become equivalent: Endless toil motivated by lapidary ideals handed down by a revered and unquestioned leader, and put into practice by a leadership caste selected for its adherence to aforementioned principles, and richly rewarded for its willingness to grind whatever human grist the mill required? Same in both.
A (mostly) pliant media that flatters the existing system of production, framing it as the only such system possible? Check! Foot soldiers who sacrifice their families and personal lives for the efficient running of the system, and who view their sole human value through the prism of advancement within that system? Welcome to the People’s Republic of Facebook. But one can simply quit a job in capitalism, while from communism there is no escape, you’ll protest.

(Here is where he bemoans how much money he needs to give his kids a life of privilege. Ah, yes, fatherhood — just like serfdom, isn’t it?)

What is writing?

It’s me, the author, taking the state inside my mind and, via the gift of language, grafting it onto yours. But man invented language in order to better deceive, not inform. That state I’m transmitting is often a false one, but you judge it not by the depth of its emotion in my mind, but by the beauty and pungency of the thought in yours. Thus the best deceivers are called articulate, as they make listeners and readers fall in love with the thoughts projected into their heads.
It’s the essential step in getting men to write you large checks, women to take off their clothes, and the crowd to read and repeat what you’ve thought. All with mere words: memes of meaning strung together according to grammar and good taste. Astonishing when you think about it.

Silicon Valley As Viewed by a Cynic

Antonio comes down hard on the Valley, though sometimes its so true it hurts. Here’s what he has to say about the place:

(Silicon Valley is) a continual self-development refracted through the capitalist prism: hippies with a capitalization table and a vesting schedule.
The human need for immortality projects — those ends that dole out meaning and purpose beyond ourselves — hasn’t changed since the pyramids. The only difference now is the nature of the putative Holy Land, and the means for achieving it.
(Silicon Valley is) the villain with a thousand faces, yoking together the monomaniac’s twitchy urge and the follower’s hunger for a role in some captivating story.
  • Investors are people with more money than time. Employees are people with more time than money. Entrepreneurs are simply the seductive go-betweens.
  • Startups are business experiments performed with other people’s money.
  • Marketing is like sex: only losers pay for it.
  • Company culture is what goes without saying. There are no real rules, only laws.
  • Success forgives all sins.
  • Meritocracy is the propaganda we use to bless the charade.
  • Greed and vanity are the twin engines of bourgeois society.
  • Capitalism is an amoral farce in which every player — investor, employee, entrepreneur, consumer — is complicit.

What rang the most true for me was The Nature of Valley Success

You try ten things, based mostly on random hunches, a few key product insights, and whatever internal mythologies your culture reveres.
Seven of them fail miserably, are discontinued, and are soon quietly swept under the rug of “forever today” forgetfulness. Two do OK, for more or less the reasons you thought, but they don’t blow the doors off your success metric. And one, for reasons you discover only after the fact, becomes a huge, transformational success.
The amnesiac tech press weaves the narrative fallacy around the proceedings, fabricating a make-believe dramatic arc from steely-eyed product ideation to flawless and unhesitating technical execution. What was an improbable bonanza at the hands of the flailing half-blind becomes the inevitable coup of the assured visionary. The world crowns you a genius, and you start acting like one. When the next usage or revenue crisis hits, you repeat the experiment, rolling your set of product dice on the big Valley table.
At some point, you don’t find the crisis-solving winner, the dealer sweeps up your remaining chips, and you’re busted. The company fails and your logo is recycled as a reminder of corporate mortality. Then everyone wonders how such a confirmed genius could have possibly failed, and ruminates on the transience of talent.

TLDR: Read this book!