
Simon & Schuster
1230 Avenue of the Americas
New York, NY 10020
www.SimonandSchuster.com
Copyright 2017 by Alexandra Wolfe
All rights reserved, including the right to reproduce this book or portions thereof in any form whatsoever. For information, address Simon & Schuster Subsidiary Rights Department, 1230 Avenue of the Americas, New York, NY 10020.
First Simon & Schuster hardcover edition January 2017
SIMON & SCHUSTER and colophon are registered trademarks of Simon & Schuster, Inc.
For information about special discounts for bulk purchases, please contact Simon & Schuster Special Sales at 1-866-506-1949 or .
The Simon & Schuster Speakers Bureau can bring authors to your live event. For more information or to book an event, contact the Simon & Schuster Speakers Bureau at 1-866-248-3049 or visit our website at www.simonspeakers.com .
Interior design by Ruth Lee-Mui
Jacket design by Alison Forner
Library of Congress Cataloging-in-Publication Data is available.
ISBN 978-1-4767-7894-5
ISBN 978-1-4767-7896-9 (ebook)
For Mom, Dad, and Tommy
The cabin was so cosy with its little doors and windows
A little chimney on it like a funny little hat;
A little flower-garden for the bees who wanted honey
Now whoever, ever saw a sweeter little house than that.
Dixie Willson, Honey Bear
Contents
Authors Note
I first met Peter Thiel, the cofounder of PayPal, managing partner of Founders Fund, and first investor in Facebook, in New York at a salon at his house in 2006. He had invited a number of friends to give presentations about religion, technology, and real estate. Over the next months and years, the tech investor and I became friends, and he introduced me to the world of Silicon Valley mania. During that time, he had all sorts of ideas that most people thought were outlandish, such as building islands with libertarian principles out in the ocean, funding longevity research, and, more recently, financing a program to encourage students to drop out of college and start companies in Silicon Valley.
All of his ideas went against political correctness. He was a contrarian and attracted equally unique friends. Through Thiel, I discovered a whole new world of often-wacky people and ideas that didnt seem to subscribe to any set principles or social awareness.
His anti-university program ended up being the one that took hold in the mind of the public. Perhaps it hit at an inflection point when Americans were fed up with paying off student debt, or they couldnt find jobs after the 2007 to 2009 recession despite having degrees, but Thiels 20 Under 20 program to grant twenty students under age twenty $100,000 to stop out of school started a new conversation about education.
The first years fellows ended up being part of my window into Silicon Valleys elite and underbelly. Through their eyes, I saw a lifestyle entirely different from the East Coasts hierarchy. Through Thiels perspective, I saw a curiosity, intelligence, and counterintuitive idealism that kept me coming back to the Bay Area more and more. This book is an attempt to capture some of the culture that attracted both me and the fellows to a place that has disrupted not only the way America does business, but also how people live their lives. In Silicon Valley, gone are the straitjacketed paths of the East Coast elite; in their place are a series of open-ended questions about which industries will be disrupted next, and which cultural configurations will supplant Old Society. Even more than a testing ground for start-ups, Silicon Valley, to me, is a larger laboratory of cultural experimentation, where the only thing thats impossible is to predict.

Prologue
I ts six oclock on a Thursday night in San Mateo County, California, at a relatively new (2009), fashionable California Craftsmanstyle hotel called the Rosewood Sand Hill. Out on the deck, which overlooks a bottom-lit Olympic-size pool skirted in fuchsias, huddles of lithe blondes in bright sundresses and billowy blouses perch on rancho-style woven ottomans near tablefuls of tech entrepreneurs outfitted in the techno-fabulous uniform of tight T-shirt, jeans, and tailored blazer. Theyre lounging under heat lamps, eating spiced popcorn and oak-grilled sliders with bottles of Sancerre wine.
This evening, however, the young blondes have competition. Every Thursday night is what regulars call Cougar Night. The cougars are women over thirty, or fortyor who dares guesson the prowl for just the sort of delicious mortals they see spread out before them right here: one tableful after another of young techies, all of them male, most of them single, half of them innocent of a womans wilesand so many of them billionaires, centimillionaires, and decamillionaires that they would make any similar assembly of investment bankers and hedge fund managers cringe from the humility of inferiority and old age.
What the women, both the young and the Botoxed, have their eyes on are young pioneers who struck it rich early on when a vast, virgin terrain called the Internet started to spread across the world in the mid-1990s. Only the young and ambitious who grew up with the computer saw it for what it might become. They had absorbed the computers digital processing early in life. To them, it didnt seem so much like a tool as it did part of their autonomic nervous systems, the part of the central nervous system that enables mammals to breathe without having to think about it. Only they could feel the boundless possibilities of the Web. Astonishingly few people born before 1970 ever got it , no matter how brilliant they might be in business or academia. The old boys looked at the Internet from the outside in and wondered what was the big deal. The digital ages children didnt have to look at it. It was in their innards. They were visionary puppies who realized that the Internet would become the worlds first great new industry in a half centurycreated, developed, operated, and, more important, owned by children. It had the potential to make television and nuclear power look like relics.
It also had entry points that had never been heard of on the East Coast. Paying your dues in Silicon Valley? Out here, that meant starting as a chief executive officer of a start-up and then failing. That was step one: the glorification of starting at the topnot the bottom or the mailroomas a founder, crashing dramatically, and then putting it on your resume as a bragging right. It was a new way of making it for those who didnt have the right pedigree. You could come from anywhere, regardless of country or degree, and there were no real steps you had to follow. The people who hit it bigand even if it was only a few billion-dollar companiesfelt like they could be the everyman, or the any-nerd. It was a hopeful message, even if it was the lucky few who crowed the loudest about their improbable leap to Silicon Valley royalty.
It was also their looks. Back home, wherever they were from, a scrawny nerd with thick glasses, baggy jeans, and a T-shirt would be unlikely to score a mate. Here at Cougar Night, women were crawling on just this type of specimen.
But how could the cougars tell who was successful and who wasnt? Everyone looked the same, from the venture capitalists to the Stanford University seniors. The former may have just dyed their hair.
The scene here at the hotel reflected the industrys first glow of glamour and turned a four-mile stretch of Sand Hill Road into a destination as magnetic as Manhattan, Londons Mayfair District, Pariss Champs-lyses, Rio, Hong Kong, Las Vegas, and the Via Veneto in Rome. In short, its the heart of the Silicon Valley, a geographical and emotional location referring to a vaguely defined fifteen-hundred-square-mile stretch beginning twenty-five miles south of San Francisco and running down the peninsula through Palo Alto and all the way to Mountain View, near San Jose.