The great source of both the misery and disorders of human life, seems to arise from over-rating the difference between one permanent situation and another. Avarice over-rates the difference between poverty and riches: ambition, that between a private and a public station:

vainglory, that between obscurity and extensive reputation. The person under the influence of any of those extravagant passions, is not only miserable in his actual situation, but is often disposed to disturb the peace of society, in order to arrive at that which he so foolishly admires. —Adam Smith, The Theory of Moral Sentiments

To paraphrase the very quotable Silicon Valley venture capitalist Marc Andreessen, in the future there will be two types of jobs: people who tell computers what to do, and people who are told by computers what to do.

One week into my new Silicon Valley life, and the lesson was this: if you want to be a startup entrepreneur, get used to negotiating from positions of weakness.

“first-party” advertiser data—the data that companies like Amazon know about you—is more valuable than most any publisher data.

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.

I gave Argyris a physical copy of “How to Start a Startup,” a blog post by Paul Graham, which is the crack-like gateway drug to the startup addiction.

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.

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.

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.

One of Mark Twain’s more uplifting quotes maintains that small people always belittle your ambitions, while the great make you feel that you too can be great.

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. Startups are experiments in group psychology. As CEO, you’re both the therapist leader, and the patient most in need of therapy.

As Geoff Ralston, a YC partner, told us: people don’t really change, they just become better actors.

As a result of the Amazon Web Services near fiasco, plus several more outages and server meltdowns, MRM suggested we run a “chaos monkey” from time to time. This was a software tool created and open-sourced by Netflix, meant to test a product or website’s resiliency against random server failures (such as we’d just witnessed with the blog).

The question for society is whether it can survive these entrepreneurial chaos monkeys intact, and at what human cost.

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.

First, the ability to monomaniacally and obsessively focus on one thing and one thing only, at the expense of

else in life.

Second, the ability to take and endure endless amounts of shit.

Unlike maniacal focus, though, which is a personality trait too difficult to mold once in adulthood, this thing—call it grit, perseverance, or whatever—is something that can be learned. If you feel you don’t possess that strength within you, then go ride a bicycle

Here’s more startup training for you: Walking into any meeting, you should know every goddamn thing there is to know about the other person; if you don’t, you’re failing. Quoth Emerson and the intro screen to Mortal Kombat 3: “There is no knowledge that is not power,” and that’s especially true in terms of people.

As true now as in Machiavelli’s time, men are judged by the company they keep.

Where do they hang out? Cheap tastes or expensive? Do they have that “lean and hungry look” of Cassius in Julius Caesar, and eat at dingy taquerias, or perhaps live off cheap staples like ramen or food substitutes? Those are the truly dangerous ones, the ones who live like organized crime trigger men, guerrilla fighters, or sailors at sea—eating shitty food and living in cheap, dumpy crash pads—and who couldn’t give a damn

about quality of life.

If you can only be good at one thing, be good at lying . . . because if you’re good at lying, you’re good at everything. —@gselevator, July 25, 2013

simple: either you’re incompetent and you struggle to provide even one answer you hope is right to the interview question, or you’re not, and your brain produces two or three. Each of those could be right, depending on your interviewer. 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.

Doing advanced studies in any quantitative field is like surviving Marine boot camp while the rest of the world is channel surfing and inhaling Oreos; you don’t exactly need to fear the push-up test.

As always, how you sell yourself is how you’ll be bought.

By itself, genius can produce original thoughts just as little as a woman by herself can bear children. Outward circumstances must come to fructify genius, and be, as it were, a father to its progeny. —Arthur Schopenhauer, “On Genius,” The Art of Literature

In general, be it at startups or aggressive companies like Facebook, there should be a cultural bias for launching.

As in life, so in business: maintain a bias for action over inaction.

This was Facebook culture for you: lots of bold, unconventional experiments, mostly failures with some notable successes, an immediate course correction to prune the failure, and then internalizing the experience via the culture. The crap murals and bluetape were as core to Facebook as the Like button (and Beacon).*

“Embracing change” isn’t enough. It has to be so hardwired into who we are that even talking about it seems redundant. The Internet is not a friendly place. Things that don’t stay relevant don’t even get the luxury of leaving ruins. They disappear.

What’s the first thing every child learns? What’s the first lesson we impart to a new pet? What makes us snap instantly out of any reverie, no matter how deep? A name. It’s simple, but magical when you think about it: you say a special word, and the person (or dog, or infant) turns and directs his or her attention at you. Involuntary and yet so fundamental, it’s practically the definition of self-awareness: I know who I am, and will respond when called.

What’s my big beef with capitalism? That it desacralizes everything, robs the world of wonder, and leaves it as nothing more than a vulgar market. The fastest way to cheapen anything—be it a woman, a favor, or a work of art—is to put a price tag on it.

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.

Real transformation happens at the first real rung on the wealth ladder. Fuck-you money is like reaching the break-even point in the startup of you, and it means you are no longer beholden to outside forces.

Here is your lesson from the Facebook IPO: whenever you see the headline “Stock X Pops on First Day of Trading and Declared a Success,” instead think “Founders and employees just got completely screwed, and the bankers and their wealthy clients made fortunes.” Because that’s what happened, and didn’t happen, in the case of Facebook.

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.

If I hadn’t become a casualty of Reesman, the God of the Chaos Monkeys,

Given all the crossed allegiances, going from the Facebook family to the Twitter one (while nominally staying inside the Facebook one at Nanigans) was no small step, and nobody in this picture, neither Facebook nor Nanigans, was bound to be very happy about it. What Twitter was asking was just shy of a breach of confidentiality, and absolute corporate treason. Just shy, which was how Silicon Valley worked. I signed the offer without negotiation, and emailed Kevin Weil to convey my eagerness to get started with Twitter. He reciprocated that excitement, and suggested a time to meet with the Twitter Ads product team. I was working for Twitter now, against Facebook’s interests, two years after very insultingly doing the opposite. At the same time I was also working for Facebook’s largest ads partner and biggest single pipe of cash. The Land of the Stateless Machines, indeed.

The way to think about startup employment is this: you’re earning the right, via your labor and time, to invest in the company, at the stock price of the last fund-raising round, just as the company’s initial venture capitalists did. That’s the real compensation you’re earning, and many a former employee agonizes over the decision of whether to plunk down the pile of money or not. If you wouldn’t invest in a company from the get-go, you’re a fool to work for it, as the cash compensation in a startup is typically woefully below market.

Among the technical, “hacking” as it’s understood among civilians—namely, illegally breaking into and messing with computer systems—is only a secondary meaning of the word. The primary meaning is the building of systems and software, with a connotation of rough tinkering rather than fine craftsmanship. “I hacked an old Windows box to run Apple OS X,” a hacker might say about some particularly interesting kludge. A “kludge,” of course, is an instance of hacking.

“Fuck-you money” is the amount of money you need to say fuck you to everybody, and live financially independently at a middle-class level in a livable city like San Francisco or Seattle.

* “Technical debt” is an oft-used concept in software development. Imagine that every time an engineer makes some quick-and-dirty fix to a piece of code—the sort of hack that will likely blow up one day and need to be fixed (again)—there’s an invisible ledger in which a loan is taken out against future engineering time. That engineer can borrow now to get the trains running again, but the bill will come due later, usually with interest.