I worked at a tech startup for about a year and a half before taking my current job at Vox. I loved it there. This gives me a pretty different perspective on Silicon Valley (by which I mean the tech startup scene in the whole SF Bay Area) than most of my coworkers, and, I’m slowly realizing, the rest of the world.



I’ve struggled a bit to come to terms with that. Did I just get wildly lucky, wandering into a unusually good company and coming away with an unreasonably rosy impression of the whole industry, an impression that could bias my coverage and do an injustice to other peoples’ real worries about startup culture in the Bay?

I think that I did get wildly lucky and land on an unusually good company. (I’m not going to name it here, though my work history isn’t hard to find if you really want to know). But I also think that my wild good luck didn’t just bias me. A pretty deeply held conviction of mine is that when you have a perspective most people don’t share, you have something of value. You don’t need to squish your worldview into theirs. You want to figure out how to convey your perspective, and then hopefully both you and them will have a richer, more complete picture of the world.



This post is an attempt to convey the perspective I gained from working at an unusually good early-stage startup in San Francisco, first as a remote contractor, then as a full-time employee, and finally as the lead on my small team. I don’t think it refutes anything else you’ve read about tech, startup culture, or the Bay. But I hope it helps make more sense of it, by explaining what exactly keeps drawing people here despite the problems and articulating why I think it’s so important that Silicon Valley exist.



i.

Starting a high-growth company is hard. I think it’s impossible to understand how hard until you’ve tried it, or seen it up close being tried. It feels like one of those tasks that humans are – just barely, kind of miraculously – capable of, and you spend a lot of time feeling like you’re not capable of it after all. It involves constant high-stakes judgment calls made with insufficient information - whether to hire, who to hire, what to prioritize, which criticisms to listen to.



It involves growing a team. Being a manager is in general an underrated skillset (perhaps because many managers aren’t very good at it). A good manager is a resource for their employees to grow, intimately understands what their capabilities and limits are so they can be assigned to tasks they can thrive at, and ensures they feel respected, valued and prioritized. A good manager at a startup has to do all of that while the company’s priorities are changing rapidly and while many employees are working on hard problems outside their core skillset. When I hear about startups with horrifyingly bad management, I am unsurprised, because this requires a level of empathy, commitment, honesty and decency that not all people can have, and it also requires a lot of practice which people only get by failing.

It involves shifting gears constantly. Sometimes you’re writing code; sometimes you’re writing copy; sometimes you’re handling office logistics headaches like how there aren’t enough desks for everybody. You’re filling in for employees who are out sick or behind on their work, and you’re meeting with investors who want to know how the million dollars they invested in you is being used. You’re tracking statistics which should warn you if the company’s growth pipeline starts to falter, while also trying to keep track of whether the numbers you’re growing are even the numbers you need to grow in order to succeed.



And once every couple years, if not more often than that, you need to make a key decision about the entire direction and future of the company, and if you bet badly the company will fail and people who (if you’re at all good at your job) you admire and care about will lose their jobs and people who trusted you with their money will lose their money.



I said before that starting a high-growth company seems to me to be a task that’s just barely within human capabilities. I think that’s actually wrong. I think it’s basically outside human capabilities, except for the fact that humans aren’t individuals, stuck trying to learn all those skills and do all those things on our own in a vacuum.



At its best, Silicon Valley is an enormous body of expertise on how to learn the skills to develop a high-growth startup. It’s a bunch of people who’ve done it before to learn from. It’s a bunch of case studies and lessons and anecdotes and warnings, many of them available on the internet in various places if you know where to look but many of them learned only from working at an early-stage startup yourself, watching and learning: “this failed because that failed. do you see what we should’ve done instead?”



The startup I worked at went through the prestigious startup accelerator Y Combinator, which gives you months of tutoring, training and support but whose primary benefit (I always assumed) was its network of alumni companies, and investors eager to invest in anything YC had put its stamp of approval on. The networking benefits of YC are very obvious. It’s not just that investors take you more seriously; people who you want to hire also tend to prefer YC startups, expecting (correctly, I think) that they’ll be better-run and have better odds of success. If you sell to other businesses, it helps with sales.



I asked my boss once what percentage of the value of YC was the label. I was thinking that the label was most of the value - any actual advice YC offered was just the icing on the cake, compared to the power of the signal.



Maybe 20% of the value comes from the signal, he said*. It took me a while to understand what else YC could possibly offer that was four times as valuable as its label.



ii.



Anything hard that humans do, we learn from other humans. And for the most part it seems like we learn best in person, from direct observation or one on one conversation. Some people can learn from YouTube videos but efforts to use them to replace education all failed. I think that there’s a part of the brain that kicks in when someone you admire sits down with you and teaches you something, which no YouTube video has yet figured out how to imitate.



In Silicon Valley there are people who will teach you to run companies. That’s what YC does, obviously, but it’s not just YC - you can get hired at a early stage company and learn how to run one that way, by observation. You can attend meetups and attend events and do the dreaded “networking” that I assiduously avoided until I became a journalist and it became my job description. In Silicon Valley there is a density of expertise on running companies that is not matched anywhere else, and that is fairly essential if you want to make a small thing grow into a big one.



And while I have no aspirations to start a company, i still valued learning those things, because the skills and lessons are a fair bit more general than that. Many of the nonprofits I admire most – 80,000 hours, the Center for Effective Altruism, Our World In Data, the ACLU – went through Y Combinator. Many of its lessons – how to refine what you do, how to make judgment calls under ambiguous circumstances, what to track and how to interpret the data you’re tracking – are lessons you need if you want to make ambitious things happen, whether you want to turn your two-person company into a billion-dollar “unicorn” or make your nonprofit great at what it does or work as a political activist.

Sometimes I contemplate starting a home daycare and I find myself drawing on those same lessons. They are useful to have. I think the sense that, if I wanted to, I could start a company makes me feel meaningfully more capable, free and independent as a human being. If I could convey them in high schools, I would, and I think our kids would come out ahead – but I’m not sure that this can be done, because an important ingredient is immersion in an environment where there are real, important stakes, and I don’t think you would replicate the important bits if you tried to reproduce it in a school.



I write a lot about the virtue called sovereignty – the belief that you are qualified to reason about your life, qualified to make important judgment calls, permitted to trust yourself and worthy of your trust. I think that at its best Silicon Valley imparts sovereignty in the only way that it can really be imparted – giving you chances to make decisions and see their consequences and learn and do better and reap the rewards of doing better.



If we, as a society, lose this expertise we will have lost something really important. And if we can make this expertise accessible to the people who don’t have access to it right now, we will have gained something really important.



iii.



One implicit assumption that I encounter frequently is that most billion-dollar companies got there by a peculiar sort of luck and privilege – wandering through a minefield full of money cannons and happening to get blasted by a particularly powerful money cannon, maybe with some tips from some well-connected Stanford classmates about where the best money cannons are hidden. I think this is almost entirely wrong.



There is indeed a bewildering amount of money flying around Silicon Valley, and it’s absolutely true that privilege matters in whether you have access to it. But I think nearly every big tech company succeeded in significant part because of the individual abilities and strengths of its leadership team, and nearly failed on the many, many occasions that it nearly failed because of the individual shortcomings and weaknesses of those same leadership teams.

In the early days of a startup, the founders make every call about who to hire, what to delegate, where to focus, what they’re building, which parts of it they’re building first. These are extremely tough calls to make, and there’s no way to outsource them, and they matter a lot. Our metrics jumped dramatically when we made good product calls – and I can only assume that there were jumps of similar size that we left on the table because we didn’t think of the idea that would have unlocked them. Screwups – even small subtle ones – cost us good people and good customer relationships.



There are probably some exceptions, but almost all startups that succeed, succeed because of the unusual competence of the people building them.

There’s a somewhat common piece of investing wisdom in Silicon Valley which is that you should invest in people, not ideas. Smart, clear-headed, good, conscientious, capable people will succeed even if they have to change ideas ten times; no idea can save people who don’t have the skills to be founders. This wisdom has the serious, perhaps fatal disadvantage that our assessment of peoples’ competence tends extremely biased towards people whose intellectual journeys matched our own. I don’t think most investors are particularly great at finding the best people or noticing them when they see them. But I do think that it’s true that investing in people is in principle the right strategy, that starting a company is basically a test of skill, with luck sufficient to sink you even if you’re skilled but not sufficient to save you if you aren’t.

The skills to start a company are, of course, learnable. I don’t have them now but I might someday. The famous founders are the young ones – perhaps because implausible trajectories are so fascinating – but most successful founders are actually older, because these skills are so decisive and they’re easier to develop with time and exposure. One of the most valuable things I got from Silicon Valley was a conviction that people aren’t interchangeable, that doing things well is in fact a skill and a learnable one, that the people I looked up to were not in fact wandering around looking for the money cannons but trying real hard to succeed at the duties they’d taken on, using skills that they had and that I wanted to acquire.



iv.



It’s time to add some caveats.



Any environment that embraces ambition and throws around a lot of money attracts people who talk a good talk and don’t do anything. I have encountered dozens of startups that were clearly, visibly a waste of money. They were going to fail and it was pretty obvious to a casual observer they were going to fail and they’d somehow been funded anyway and then they failed. I don’t think this is a necessary price of having the nice things about Silicon Valley, though I worry a little bit that external intervention to prevent it would accidentally break something that is a crucial component of Silicon Valley’s capacity for achieving important things.



There are a lot of people who don’t have access to Silicon Valley. In particular, more than six billion people, the vast majority of all the people alive today, are prohibited by law from living and working in Silicon Valley no matter how desperately we’d like to hire them and no matter how interested they are in working here. There are gifted men and women who will die in poverty because the law does not allow U.S. companies to hire them, or puts such strict conditions on that hiring that small companies stand no chance of navigating it.



There are other people who are permitted by law, but prohibited by a bunch of other factors, from working in Silicon Valley. One such factor is the outrageous cost of housing in the Bay Area, which makes it extremely hard for poor Americans to move out here to hunt for work, or to support their families even with a tech salary. Another one is the presence at some companies of sexist jerks who treat the women who work for them as less valuable, less skilled and less capable than the men who work for them, and the presence of invisible social, racial and class barriers that make working at Silicon Valley more of a real option for people from some backgrounds than others.



None of the things I have to say about Silicon Valley should be evaluated as reasons not to care about these things - if anything, they’re reasons to care way more about those things than you already did, because if Silicon Valley really has something of profound value to offer the world then it’s extra concerning if not everyone has access to it.



But I think there are a few different ways to approach the issue of diversity and inclusion. One is that a culture or environment is bad, and it needs ‘better’ people to fix it. I dislike that one. I think it’s essentializing and a bit dehumanizing - I want to be recognized as an employee and as a human being, not as a supply line of moral goodness for the company I work for. Another perspective is that a culture or environment is valuable, and does important things, and so it’s essential that every person have meaningful access to it and the ability to participate in it and participate in improving it. I care deeply about that one. It’s in that spirit that I want to articulate what Silicon Valley can be at its best.



v.



What does it mean to be a society where people can do hard things?



One thing it means is that we have to be forgiving of failure. Sometimes when you try to do hard things you’ll screw up; a society where people can’t screw up without having it held against them forever is a society where people will slowly lose a lot of ability to do hard things. A good thing about Silicon Valley is that it’s unusually tolerant of resume gaps, of college dropouts, of nontraditional educational pathways. It has to be; if people are doing hard things, then many of them will not have prestigious and reassuring pedigrees. In most of the country, a failed startup or a short tenure at a company looks pretty bad on your resume. In the Bay it’s held against you a lot less.



Related to that is tolerance for weirdness. Tolerance for weirdness can be a double-edged sword, in that it gets used as cover by scam artists and can make it harder for people to articulate when someone else is acting inappropriately. But many good, valuable ideas are weird. Many companies that we now take for granted started out as a weird idea that turned out to just need some refining (AirBnB started out hosting people on air mattresses, thus the “Air”).



And more than that, many people are weird. I and many of my friends are or at various points have been disabled, and among the accommodations we need to work are: meals provided in the office, beanbags and couches to work on, hours that start at 11am, electric scooters (yes, really), noise-cancelling headphones, bouncy balls, places to nap at work, and extended mental health leave. It’s because that’s the background I’m coming from that I tend sympathetic towards the health, diet and exercise fads, the standing desks, the productivity apps. People need different environments and supports to get hard things done. For anything that’s easy to dismiss as a dumb fad, there is probably someone for whom it’s a necessary support in doing hard things – and if we want to enable people to do hard things, we need to let them have it.

Contempt for other people just because they’re weird and waste their time on stupid things is bad for people, and it’s bad for the culture of Silicon Valley, and I think it’s getting worse over time as the internet has explored its potential to make mockery easier faster than it’s explored its potential to make understanding easier.



As a culture gets more “serious” – is understood to be operating with real-world political and social stakes, is under more mainstream scrutiny – its tolerance for weirdness necessarily goes down. This gets in the way of the ability to do hard things, and that’s not great for anyone. I have a strong instinct that if something is weird but people value it, then probably it’s important actually even if I don’t see how – and I think this instinct is true, and justified, and one you can cultivate by talking to enough people with different needs. The best engagement with the Bay Area is engagement that takes a stance of genuine curiosity about why weird things work for people, and the worst engagement is the engagement that encourages people to point and laugh at others for being weird.



vi.



But isn’t tech destroying the world?



I feel like I have credentials from both sides of this argument here. I just wrote a couple thousand words about how awesome tech can be; I’ve also written a couple thousand words about why I think that AI advances may cause the annihilation of the human race.



I think that tech has created a bunch of problems that no one - including them but also including the rest of us - knows how to solve. And that’s terrifying, and it’s forcing a reckoning that obviously had to happen but that also is not yet showing signs of making things better.



At the end of the day that’s the reason I’m writing this. For a long time it felt like the rest of the world merrily appreciated the good stuff coming out of Silicon Valley and laughed at the bad stuff and the fact that tech was fundamentally on a different wavelength than the rest of the world didn’t really matter. No one understood Silicon Valley but, like, Silicon Valley sure didn’t understand Miami either, so it was all even.



But now tech is at the center of social problems that every single person deserves a voice in solving. Facial recognition is being put to sketchy uses by authoritarian governments. People are raising questions about whether the optimization power of Facebook and YouTube’s algorithms makes them too good at increasing engagement and a net harm to their users. The Pentagon wants to partner with Google on drone strikes. Companies which never wanted to have content moderation abilities are trying to figure out how to moderate content anyway out of necessity, and they’re really bad at it. And there’s no reason to expect any of this to get easier with time, and a lot of reason to expect it to get harder as machine learning systems develop more capabilities and get even better at optimizing for whatever dubious target they’re pointed at.



But to fix any of that, we need to all be on the same page. It’s hard to fix an industry as an outsider – people bristle at being misunderstood, and they don’t take solutions seriously from people they see as part of the problem. And a lot of potential fixes, like breaking up all tech companies automatically when they reach a certain size, would probably rip up most of the good things about Silicon Valley.

I genuinely think any conversation about fixing tech has to start by building this particular bridge right here – between people who had good experiences and people who had bad experiences, between people who are holding on to something valuable they need to preserve and people who can’t see any value in it.







* This conversation was a long time ago and I might be off by up to 10% in either direction.