Inside Silicon Valley
Uncanny Valley

Inside Silicon Valley

New York Times bestselling writer Anna Wiener presents an insider portrait of Silicon Valley at a crucial moment in history and explains how that moment changed her life.

In this New York Times bestseller – which the Times, Washington Post, Atlantic, NPR, Los Angeles Times, Esquire, Self and myriad more publications chose as a Best Book of the year – New Yorker contributor Anna Wiener details the seductions and toxins of Silicon Valley’s money, ambition and optimism.

A New York intellectual out of place in the misogyny and bro-hood of the tech universe, Wiener writes with equal insight and eloquence about the consciousness and senseless rituals and norms of Silicon Valley and their oppressive effect on her.

Start-up Tech World

Wiener explains that for denizens of Silicon Valley a certain moment marked either the peak of the frenzied start-up scene or the harbinger of its end. Social media’s defining company had gone public for billions. Employees saw a utopian future and found their roles in it intoxicating. Artificial intelligence (AI) was ascendant, and self-driving cars loomed on the horizon.

It was the dawn of the era of the unicorns: start-ups valued, by their investors, at over a billion dollars. A prominent venture capitalist had declared in the op-ed pages of an international business newspaper that software was eating the world.Anna Wiener

People in tech didn’t believe in boundaries or limits on their freedom to transform their ideas into future reality. Money flowed, pulling in talented engineers and elite MBAs.

A Passing Fad

Wiener didn’t know about what was happening in Silicon Valley or how it would change everyone’s lives. She describes herself as a university graduate in her mid-20s working in a New York City literary agency.

Meanwhile, the industry expanded beyond the province of futurists and hardware enthusiasts, and settled into its new role as the scaffolding of everyday life. Anna Wiener

Wiener resented Facebook because it enabled her discovery of her boyfriend’s infidelity, and she knew Amazon was obliterating the publishing industry. She read about three young men who had gotten a lot of money to transform the publishing industry by developing an e-reading app for mobile phones. Seeing e-book apps as the future of publishing, she got a job at the e-book start-up.

Big data

The start-up’s founders didn’t care about literature and didn’t care if the digital world undermined the market for books and culture. Wiener understood her main function was to be decorative, since the industry recognized its lack of diversity and its dearth of women in positions of authority. Eventually, though, her employer told her she wasn’t the right kind of person for the company.

Wiener moved to San Francisco. She had university friends there living lives of hallucinogens, sex parties and bands – the kind of people her New York friends laughed at. She endured the strange interview process at a data analytics start-up – the Valley was famous for disruptive interviews – and got the job, which paid a grown-up, above-market salary. The money enthralled Wiener. It was more than she had imagined earning. 


Wiener wanted her life to move forward, so she owned her ambition. As she acknowledges, she was “spoiled” by the tech industry’s feeling of boundless potential and its lightning pace.  The analytics start-up devised a crucial tool that everyone in the expanding digital world could use, the kind of thing venture capitalists support because the company would market it to other businesses, not consumers. Wiener was the company’s 20th employee, joining three other women.

Work AS Identity

San Francisco was once a haven for hippies, beat poets and gay activists. The newly arrived tech people were mostly heterosexual men obsessed with money and power. These transplants weren’t comfortable with the city’s left-wing politics and broad tolerance. Their dislike of unreliable public transport inspired a ride-sharing start-up. Skyrocketing rents and high-end developments spawned numerous homeless encampments.

I had never seen such a shameful juxtaposition of blatant suffering and affluent idealism.Anna Wiener

Wiener’s start-up rocketed past its competitors. Everyone worked so much that work became integral to people’s identities. The constant forward momentum produced euphoria. However suspicious she might have been of that euphoria, Weiner felt it, too.

An Alien World

Wiener grew accustomed to talking about tech with engineers. She gave training webinars for new customers and made her way across model data sets. She reassured people about data, software and servers, making customers feel that everything was fine and that they received real value for the fees they paid the company.

Some days, helping men solve problems they had created for themselves, I felt like a piece of software myself, a bot.Anna Wiener

At the CEO’s behest, Wiener learned to code. Tech people explained that writing code expanded and illuminated the world. With code, they could create anything they could imagine. Writing code wasn’t difficult, and its precision and clarity engaged Weiner. But working in technology without a tech sensibility was like living in an alien world. Still, she got a $10,000 raise.

A Leak

A National Security Administration (NSA) whistleblower released classified documents and information. The leaks exposed the United States government’s surveillance efforts and showed that NSA monitored people’s private exchanges via phone, text and email as well as on various social networks without anyone’s consent or knowledge.

If anyone raised concerns about the information our users were collecting, or the potential for abuse of our product, the solutions manager would try to bring us back to Earth by reminding us we weren’t data brokers.Anna Wiener

No one at Wiener’s company considered how they enabled the creation of massive, privately owned databases that documented human activities – databases ripe for government spying. Company managers assured everyone they held the high moral ground.


Wiener relates that the future came to look strange and indeterminate, while the present seemed precarious. People in the Valley had started out trying to create a better world and ended up just trying to hold on.

Wiener knew her pay was good, and her lifestyle was comfortable. But the work left her with a yawning emptiness. She had spent years disassociating and thinking of her life in technical, systems languages. Wiener wanted to be a writer, so in the end, she quit.

Cultural and Personal Insights

Many reviewers pigeonholed Wiener’s work as a scathing attack on misogyny and bro-hood in Silicon Valley. Deliberately or not, they reduced her rich psychological portraits and brooding, revelatory self-insights to clichés, but they were wrong. First, she doesn’t deal in clichés. Wiener stands out as an exemplar of her generation and of a certain moment in history to those younger and older who want to understand this culture and its impacts. She is a witty, poetic writer with great insight into how certain telling moments can define an era and mark her personal evolution. She provides both autobiography and social and economic history.

Other insightful books about Silicon Valley include Valley of Genius: The Uncensored History of Silicon Valley by Adam Fisher; The Code: Silicon Valley and the Remaking of America by Margaret O’Mara; and Bad Blood: Secrets and Lies in a Silicon Valley Startup John Carreyrou.

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