Inside the Mirrortocracy
"It is difficult to get a man to understand something when
his salary depends upon his not understanding it."
— Upton Sinclair
There's a problem with Silicon Valley and the subcultures that imitate it. It's a design bug woven into people's identities and sense of self-worth. Fixing it will be painful. Influential and otherwise very smart people will deny till their last breath that it even exists. But I believe it should be fixed before it gets any worse.
Since credentials are so important these days, here are mine. I'm a progammer, and a good one. I've worked at several companies that went on to be acquired and one that went IPO. I've founded companies and conducted hundreds of interviews. I've written well-respected books, am regularly invited to speak, and have been honored by the White House for my work teaching computer science to children. I've devised novel ways to optimize billion-dollar computer clusters so that they don't become two-billon dollar computer clusters. You have almost certainly run code that I wrote. 
I wouldn't make it past the résumé screen if I were starting my career today.
About twenty years ago I enrolled in a dropout-prevention program at my high school. It allowed me to attend class only half the day. In the afternoons I worked at a startup. The early 90s were a wild time. Any idiot who could spell "HTML" could get a job and I was one of them. It didn't matter that I had half a high school diploma and no driver's license. They gave me a shot and I ran with it.
The general quality and professionalism of programming has gone up since then. That is a good thing. That's not the problem.
The problem is that Silicon Valley has gone completely to the other extreme. We've created a make-believe cult of objective meritocracy, a pseudo-scientific mythos to obscure and reinforce the belief that only people who look and talk like us are worth noticing. After making such a show of burning down the bad old rules of business, the new ones we've created seem pretty similar.
"The notion that diversity in an early team is important or good
is completely wrong. You should try to make the early team as
non-diverse as possible."
— Max Levchin
Max Levchin, a founder of PayPal, preaches that mythos to young hopefuls who want to follow his success. His thinking is actually more subtle than that quote, but subtlety and introspection are not common traits among young people out to make a lot of money in a short period of time. Encouragement from billionaire heroes leads to even more insularity.
Because the talent market is tight, that insularity presents a problem. It's hard to find good people to hire. All the Stanford graduates have offers from multiple companies and there's no time to develop talent. On the other hand, so many nice-seeming candidates seem to fail the interview process for trivial mistakes that fall under the catch-all category of "culture fit".
Nerdsplaining
The solution, of course, is not self-reflection or asking hard questions about the values and assumptions that form the process. The solution is to write "explainer" blog posts to initiate candidates into the Culture. As the hiring crunch gets more desperate, examples of this genre are more frequent. They are fascinating documents of just how disconnected insiders have become from the very people they are trying to hire. Here's an excerpt from the blog of a San Francisco startup [cached version]: 
I asked her how she was doing in the interview process and she said, “I’m actually still trying to get an interview.”
“That’s weird.” I told her. “I thought you had already met with them a few times.”
“Well, I grabbed coffee with the founder, and I had dinner with the team last night, and then we went to a bar together.”
I chuckled. She was clearly confused with the whole matter. I told her, “Look, you just made it to the third round”.
Clearly, the confusion is her fault, right? Let's review the bidding. A capable professional expressed interest in working for a company. Instead of talking with her about that in plain English, she was held at arm's length for days while The Culture examined her for defects: coffee dates in the afternoon, conversations over dinner. When she gets the invisible nod, her reward is a "spontaneous" invitation to a night of drinking with the team. You have to wonder why intelligent people would devise an interview process so strange & oblique that the candidate doesn't even know it's happening.
On the surface there's nothing wrong with getting to know a job candidate in a relaxed setting. But think about who might flunk this kind of pre-interview acculturation. Say, people who don't drink. Or people with long commutes, or who don't have the luxury of time to stay out late with a bunch of twenty-somethings on a whim. Or, perhaps, people who don't like the passive-aggressive contempt shown to those who don't get with The Culture.
Ignorance of The Culture is a serious handicap if you want to land a job out here. Another story from same post is very tense. (The emphasis is mine.)
We had a gentleman over to interview for one of our account executive positions... great resume, great cover letter, did well in our initial phone screen.
He was dressed impeccably in a suit... I stole a glance to a few of the people from my team who had looked up when he walked in. I could sense the disappointment.
It’s not that we’re so petty or strict about the dress code that we are going to disqualify him for not following an unwritten rule, but we know empirically that people who come in dressed in suits rarely work out well for our team.
He was failing the go-out-for-a-beer test and he didn’t even know it...
I told him he could take off his tie and jacket and loosen up a little bit, and he acknowledged that he felt a little out of place but said that, “you can never overdress for an interview.”
Well, dude, no, actually you can overdress for an interview and you just did. Of course I didn’t say it...
The cognitive dissonance is painful to witness. Clothing is totally not a big deal! Because we're cool like that! But it's plain that it biased the interviewers. The team's disappointment upon seeing the suit was immediate and unanimous. If you truly believe that suit == loser, you can't help it. Nevertheless, the fiction of objectivity has to be maintained, so he denies it to the candidate's face, to us, and himself. 
Remember that the entire point of his article is to convince candidates to look and act differently: "it’s your responsibility to learn [our] cultural norms." Presumably that same account exec is supposed to take the hint, dress in mufti, and do better at his next startup interview. But of course, how you dress is totally not a factor in the scientific decision process.
Even if you take his statements at face value they make no sense. Suppose that it's a scientific fact that wearing a suit signals that a candidate is unfit for duty. Assuming that's true, then what does teaching the poor bastard how to camouflage himself actually accomplish? Does clothing indicate a person's inner qualities or not? What, exactly, is the moral we're supposed to learn from this grubby little drama?
The theme is familiar to anyone who's tried to join a country club or high-school clique. It's not supposed to make sense. You are expected to conform to the rules of The Culture before you are allowed to demonstrate your actual worth. What wearing a suit really indicates is —I am not making this up— non-conformity, one of the gravest of sins. For extra excitement, the rules are unwritten and ever-changing, and you will never be told how you screwed up.
"PayPal once rejected a candidate who aced all the engineering tests because for fun, the guy said that he liked to play hoops. That single sentence lost him the job."
— Max Levchin
Clothing is the least of it. Your entire lifestyle and outside interests are under examination, as is your "commitment". Say you're asked out for coffee on short notice, which you decline because you're busy. Is that a "ding"? Did that lose you the job? Who knows? Maybe it did. You're still trying to figure out what they mean by "wowing" them. Should you ask? Maybe you'll seem desperate if you ask. Oh, shit!
The obscurity and arbitrariness are very much by design, and is why explainer posts are supposed to be so valuable. Having engineered an unfair situation, insiders then offer secret guides to winning it.
How to make it in the Valley
As far as I can tell, these are the seven rules to follow if you're going to have a chance at being snubbed by a Valley Culture startup. The initial gauntlet is not as harsh if you possess trendy technical skills but that is by no means a free ticket. 
- Live in the Valley. If you don't, move. The pioneers who are connecting the global human family and removing barriers of time and space won't take you seriously unless you brunch at the same restaurants they do. Ideally you should live in "The City", which is on a peninsula, and not on "The Peninsula", which is in a valley.
- We expect you to click with us "organically", which means on our schedule. Be flexible with your time. It's best to behave as though you have nothing better to do all day but wait for us to call you in for coffee or some skateboarding.
- Don't overdress, but don't underdress. You should mirror as precisely as possible our socioeconomic level, social cues, and idiom. Remember unlucky Mr Hoops. But no pressure, you know? Laid back.
- To distinguish yourself from the throngs, find a way to surprise us that has nothing to do with your ability to perform your job. Maybe you could bring some appropriately quirky luxury foods as tribute.
- You are expected to read everything we blog about and work it into the conversation. This shows commitment.
- We don't actually want to talk to you. You need to locate someone else in our social circle and convince them to send us a "warm intro". This is a wonderfully recursive time-waster, as those people will want a warm intro from someone they know before talking to you, and so on.
- We're objective meritocratic folks and will violently reject any suggestion that we are not. We totally won't "ding" you for not doing steps 1-6, we swear. But they help. Totally.
Watch yourself
The problem with gathering a bunch of logically-oriented young males together and encouraging them to construct a Culture gauntlet has nothing to do with their logic, youth, or maleness. The problem is that all cliques are self-reinforcing. There is no way to re-calibrate once the insiders have convinced themselves of their greatness.
It's astonishing how many of the people conducting interviews and passing judgement on the careers of candidates have had no training at all on how to do it well. Aside from their own interviews, they may not have ever seen one. I'm all for learning on your own but at least when you write a program wrong it breaks. Without a natural feedback loop, interviewing mostly runs on myth and survivor bias. "Empirically", people who wear suits don't do well; therefore anyone in a suit is judged before they open their mouths. On my interview I remember we did thus & so, therefore I will always do thus & so. I'm awesome and I know X; therefore anyone who doesn't know X is an idiot. Exceptions, also known as opportunities for learning, are not allowed to occur. This completes the circle.
You can protest your logic and imparitiality all day long, but the only honest statement is that we're all biased. The decisions of parole judges, professionals who spend their entire careers making decisions about the fate of others, are measurably affected by whether they had just eaten lunch. And that's with a much more rigorus and formal process whose rules are in the open. But you're sure your process is totally solid, right? 
If spam filters sorted messages the way Silicon Valley sorts people, you'd only get email from your college roommate. And you'd never suspect you were missing a thing.
“I want to stress the importance of being young and technical.
Young people are just smarter.”
— Mark Zuckerberg
I was in the audience when a 22-year-old Zuck led with that drop of wisdom during his first Startup School talk. It wasn't a slip of the tongue, it was the thesis of his entire 30 minutes on stage. It would have been forgettable startup blah-blah except that his talk followed Mitch Kapor's. The contrast could not have been more raw. Ironically, Zuck had arrived late and didn't hear Kapor speak. He's since evolved his views, thanks to Sheryl Sandberg's influence and (ahem) getting older himself.
Kapor is the legendary founder of Lotus, which more or less kicked off the personal computer revolution by making desktop computers relevant to business. He spoke about the dangers of what he called the "mirror-tocracy": confirmation bias, insularity, and cliquish modes of thinking. He described the work of his institute to combat bias, countering the anecdotes and fantasies that pass for truth with actual research about diversity in the workplace.
The first step toward dissolving these petty Cultures is writing down their unwritten rules for all to see. The word "privilege" literally means "private law". It's the secrecy, deniable and immune to analysis, that makes the balance of power so lopsided in favor of insiders.
Calling it out and making fun of it is not enough. Whatever else one can say about the Mirrortocracy, it has the virtue of actually working, in the sense that the lucky few who break in have a decent rate of success. Compared to what, well, that is carefully left unasked. The collateral damage of "false negatives" is as large as it is invisible. But it is difficult to argue with success. It takes a humility and generosity that must come from within. It can't be forced on others, only encouraged to develop.
Lest you get the wrong idea, I'm not making a moral case but a fairly amoral one. It's hard to argue against the fact that the Valley is unfairly exclusionary. This implies that there is a large untapped talent pool to be developed. Since the tech war boils down to a talent war, the company that figures out how to get over itself and tap that pool wins.
So the second step is on you. Instead of demanding that others reflect your views, reflect on yourself. Try to remember the last time someone successfully changed your mind. Try, just for a moment, to suppose that it's probably unnatural for an industry to be so heavily dominated by white/asian middle-class males under 30 who keep telling each other to only hire their friends. Having supposed that, think about what a just future should look like, and how to get there.
You want a juicy industry to disrupt? How about your own?