The head of the initiative was the former CEO of a website that served as a repository of humorous images and videos optimized for social media virality—mostly cats doing improbable things, like riding robotic vacuum cleaners and getting stuck in hamburger buns. The website had raised nearly forty-two million dollars in venture capital. He would be working alongside another entrepreneur, a woman who had founded an on-demand housekeeping platform that had shut down amid a spate of lawsuits. The audacity was breathtaking.

The VCs were prolific. They talked like nobody I knew. Sometimes they talked their own book, but most days, they talked Ideas: how to foment enlightenment, how to apply microeconomic theories to complex social problems. The future of media and the decline of higher ed; cultural stagnation and the builder’s mind-set. They talked about how to find a good heuristic for generating more ideas, presumably to have more things to talk about.

Despite their feverish advocacy of open markets, deregulation, and continuous innovation, the venture class could not be relied upon for nuanced defenses of capitalism. They sniped about the structural hypocrisy of criticizing capitalism from a smartphone, as if defending capitalism from a smartphone were not grotesque. They saw the world through a kaleidoscope of startups: If you want to eliminate economic inequality, the most effective way to do it would be to outlaw starting your own company, wrote the founder of the seed accelerator. Every vocal anti-capitalist person I’ve met is a failed entrepreneur, opined an angel investor. The SF Bay Area is like Rome or Athens in antiquity, posted a VC. Send your best scholars, learn from the masters and meet the other most eminent people in your generation, and then return home with the knowledge and networks you need. Did they know people could see them?

The rationalist swept her hair behind one ear. Contrarianism was underrated, she said. The intellectual contributions were, on net, positive. It was difficult to judge, in the present moment, which ideas would hold water; thus, better to err on the side of more debate, rather than less. “As an example, think of the abolitionists,” she said. I asked what the abolitionists had to do with libertarian contrarianism. “Well,” she said, “sometimes minority opinions lead to positive and widespread adoption, and are good.”

As a neutral statement, this was hard to disagree with. Some minority opinions did lead to positive change. I wanted to give her the benefit of the doubt. But we weren’t talking about a neutral statement. We were talking about history.

I took a sip of red wine from a glass that I hoped was mine, and ventured that the abolition of slavery was perhaps not a minority position. Slaves themselves were surely abolitionists, I said. Just because no one was polling them didn’t mean they did not exist. I was trying to be lighthearted. I was trying to be kind. I was trying not to embarrass both of us, though that ship might have already sailed.

The rationalist turned to look wistfully at the other partygoers, now gathered in the living room and happily instructing a virtual-assistant speaker to play workout music. She sighed. “Okay,” she said. “But, for the sake of argument, what if we limit our sample to white people?”

With another early employee of the analytics startup, Noah was prototyping an app—application—to facilitate collective action in the workplace. “The critique, of course, is that we’re monetizing labor organizing,” Noah said when I went to see him in Berkeley. His cofounder saw it as a way to make capitalism function better, more efficiently; needless to say, the latter would be the investor pitch. They had considered going through the seed accelerator, until doing thirty seconds of research: Any industry that still has unions has potential energy that could be released by startups, the seed accelerator’s founder had microblogged. The accelerator claimed to want people who wanted to beat the system, but a tool for organizing workers was perhaps beating the system too hard. The wrong type of collaboration software.

[...] My reasons for deflecting and deferring were pragmatic—money, social affirmation, a sense of stability—but they were also personal. I still clung to the belief that I could find meaning and fulfillment in work—the result of over two decades of educational affirmation, parental encouragement, socioeconomic privilege, and generational mythology. Unlike the men, I didn’t know how to articulate what I wanted. Safer, then, to join a group that told itself, and the world, that it was superior: a hedge against uncertainty, isolation, insecurity.

These motivations were not aging well. In reality, there was nothing superior about those whom I was trying to impress. Most were smart and nice and ambitious, but so were a lot of people. The novelty was burning off; the industry’s pervasive idealism was increasingly dubious. Tech, for the most part, wasn’t progress. It was just business.

This was both a relief and a disappointment. It was also, perhaps, the root of my empathy for the young entrepreneurs of Silicon Valley. Many of them were at least a decade deep into lives they had selected for themselves as teenagers. Surely, I thought, some must have wanted to try something different, get off the ride. Surely some were beginning to have moral, spiritual, political misgivings. I was radiant with projections.

I was always looking for the emotional narrative, the psychological explanation, the personal history. Some exculpatory story on which to train my sympathy. It wasn’t so simple as wanting to believe that adulthood was a psychic untangling of adolescence, willful revisionist history. My obsession with the spiritual, sentimental, and political possibilities of the entrepreneurial class was an ineffectual attempt to alleviate my own guilt about participating in a globally extractive project, but more important, it was a projection: they would become the next power elite. I wanted to believe that as generations turned over, those coming into economic and political power would build a different, better, more expansive world, and not just for people like themselves.

Later, I would mourn these conceits. Not only because this version of the future was constitutionally impossible—such arbitrary and unaccountable power was, after all, the problem—but also because I was repeating myself. I was looking for stories; I should have seen a system.

I was lucky. Draining my bank account to exercise my stock options was only tenable because I knew I could borrow money from family, or from Ian. Some of my coworkers, largely women in nontechnical roles whose work had been foundational to the company, but whose salaries did not allow them to save much in the city with the highest cost of living in the country, had been offered generous stock grants that they were unable to exercise after they left the company. Some women, I had heard, were promised extensions on their exercise windows, only to have the extensions vetoed by the board after the grants had expired. The acquisition was a once-in-a-lifetime bonanza. It passed them by.

Flat structure, meritocracy, non-nonnegotiable offers. Systems do work as designed.