by Anna Wiener
Not just a diamond, a mine. A significant fraction of my former coworkers became millionaires and multimillionaires; the founders became billionaires. The venture capitalists refueled. I was happy for friends, especially lower-level employees who had worked incredibly hard, and I was excited for their families, for whom a low-six-figure exit would be life-changing. I wondered if the company would develop an internal class hierarchy, then remembered it already had one.
The shares I exercised were worth about two hundred thousand dollars, before taxes. This was a windfall by my standards, if modest for the industry: it was less than the median salary at the social network everyone hated; less than the six hundred thousand dollars direct-deposited into an early support rep’s bank account; less than the multimillion-dollar sums that went to people I suspected had done indelible harm to coworkers. I felt no pride, only relief and guilt.
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.
* * *
That same spring, the CEO of the analytics startup stepped down. “I just need a break,” he told a business reporter. “It’s been a marathon.” On social media, he joined the ranks of industry thought-leaders contributing to the founder-realism genre, recommending therapy and community, microblogging his own emotional development in real time.
In the chat room for ex-employees of the analytics startup, my former coworkers lauded the decision. They joked about inviting the CEO to the channel. They rolled their emoji-eyes at his inspirational posts. They reminisced about the early team, griped about the CEO, and debated, as former employees of still-private companies were wont to do, whether our own stock options would ever be worth anything. I wondered if it had been traumatic for the CEO to leave the company he built, if it felt like grief. I wondered if he had regrets, and how long it would be until he did it all again.
Within a year of the CEO’s departure, the CTO and several engineers would return to the analytics startup to see it through. I wondered if they felt a loyalty to the product—if they would not be satisfied until the problem, technically speaking, was solved. I understood the appeal of returning to the company, though I knew I never could. It wasn’t just that I had traded the security of tech for more engaging work—and was hoping, against the odds, that it would last—but that I couldn’t imagine once again being so complaisant, so consumed.
A few months later, I wandered through the Mission, killing time before meeting a friend for lunch. Sitting outside a fast-casual Greek restaurant on Valencia Street were two men engaged in animated conversation, their napkins wadded on the table. Nearly five years had passed, but I recognized the CEO of the analytics startup immediately: gelled hair, slight frame, green jacket. He looked happy, relaxed, older. He looked just like anyone else.
Weekday lunch on the town, I thought—good for him. Then I turned and walked as quickly as possible in the opposite direction. I am confident he never saw me.
ACKNOWLEDGMENTS
I am immensely grateful to Daniel Levin Becker, Molly Fischer, Henry Freedland, Jen Gann, Sam MacLaughlin, Manjula Martin, Emily Nakashima, Meaghan O’Connell, Hannah Schneider, and Taylor Sperry, for their intellectual generosity and editorial insight. I am thankful to Nick Friedman for early, foundational conversations. Thank you to Moira Weigel for her friendship and intelligence, and for always offering the systems view. Thank you to Gideon Lewis-Kraus, for wild kindness at every stage.
Thank you to Mark Krotov, for genius edits and unfailing support of this project. Thank you to Dayna Tortorici, for encouraging me to write about San Francisco and startup culture in 2015, and for brilliant editorial advice. I am indebted to n+1: thank you for taking a chance on me.
Thank you to Chris Parris-Lamb, for developing this book alongside me, and for being a constant source of wisdom, advice, clarity, humor, and support; truly beyond. Thank you to Sarah Bolling, for sharp and understanding notes, and to Rebecca Gardner, Ellen Goodson Coughtrey, and Will Roberts, for bringing this book to readers abroad.
Thank you to my editor, Emily Bell, for believing in this project from the beginning, and for being a fierce advocate at every stage. Thank you to the team at MCD / Farrar, Straus and Giroux, especially Jackson Howard, Naomi Huffman, Sean McDonald, and Sarita Varma. Thank you to Rebecca Caine for her thoughtfulness and poise while working on this manuscript, and to Greg Villepique, Chandra Wohleber, Kylie Byrd, Kathleen Cook, Nina Frieman, Jonathan Lippincott, and Gretchen Achilles, for their attention and care. Thank you to Anna Kelly, Caspian Dennis, and Sarah Thickett, for championing this book in the U.K.
Thank you to Jason Richman, for his exuberance and insight, and to his team at UTA. Thank you to Johnny Pariseau and Alison Small, for their excitement, integrity, and open-mindedness. Thank you to Michael De Luca Productions and Brownstone Productions. I am grateful to Sara’o Bery for his frank, crucial advice.
Thank you to Emily Stokes, for working closely on sections of this book, and for being a wise and generous sounding board. Thank you to Michael Luo, Pamela McCarthy, David Remnick, and Dorothy Wickenden for offering me a place to continue writing about tech culture. Thank you to Carla Blumenkranz, Anthony Lydgate, and Daniel Zalewski. Thank you to Joshua Rothman for his insightful, enriching editing on my Silicon Valley dispatches.
Thank you to Leah Campbell, Danilo Campos, Patrick Collison, Parker Higgins, Cameron Spickert, and Kyle Warren, for their friendship and trust. Thank you to David Gumbiner. Thank you to my former coworkers at the analytics and open-source startups, especially those who took the time, and some risk, to speak with me for this project. Thank you to dear friends in California and New York, so many of whom have helped untangle my thoughts about labor, life, art, capitalism—like anything, a work in progress.
Thank you to the Shermans, north and south, for their kindness and encouragement. Thank you to my family, especially David and Marina Wiener. Thank you to Dan Wiener and Ellen Freudenheim, for their enthusiasm and guidance. I am grateful to Ian Sherman for his love, for his steady support of my writing, and for always asking the right questions.
A NOTE ABOUT THE AUTHOR
Anna Wiener is a contributing writer to The New Yorker, where she writes about Silicon Valley, startup culture, and technology. She lives in San Francisco. Uncanny Valley is her first book. You can sign up for email updates here.
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CONTENTS
Title Page
Copyright Notice
Incentives
Scale
Epilogue
Acknowledgments
A Note About the Author
Copyright
MCD
Farrar, Straus and Giroux
120 Broadway, New York 10271
Copyright © 2020 by Anna Wiener
All rights reserved
First edition, 2020
E-book ISBN: 978-0-374-71976-0
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This book is a memoir. It reflects the author’s present recollections of experiences over time. In some instances, events have been compressed and dialogue has been re-created. The names and identifying characteristics of some persons described in the book have been changed.
