Silicon Valley’s Most Disturbing Obsession

The Rand Pack

Silicon Valley’s Most Disturbing Obsession

It’s not artificial intelligence, or even perfecting the “smart juicer.” It could be a lot more sinister.
The princes of Silicon Valley—including Kevin Systrom, Travis Kalanick, EvanSpiegel, and Jack Dorsey have learned a lot from tech idol Ayn Rand.
Photo Illustration by Tamara Shopsin. Photographs by Vivien Killilea (Spiegel), Brent Lewin/Bloomberg (Kalanick), David Paul Morris/Bloomberg (Dorsey), Oscar White/Corbis/Vcg (Rand), all from Getty Images; By Matt Edge/The New York Times/Redux (Systrom).

‘At the moment, I’m completely absorbed with end-of-year projects at school,” the e-mail read. It was 2012, and I was working on an article about an innovative new app that was being used by a handful of high-school students in Los Angeles. It had never been written about before, and so I found myself tracking down its co-creator, a freshman at Stanford. Evan Spiegel was elusive. He wasn’t secretive or a jerk, but just had a lot of homework to do. The day after the story was published, he e-mailed me: “If I fail my E40 midterm on Friday because of all this media attention I know who to blame ;)”

I had a similar experience at a tiny coffee shop near South Park, in San Francisco, when a young man named Kevin Systrom sipped an espresso and prodded his phone to show me an app he had recently launched: Instagram. This, in turn, reminded me of a meeting I’d had, a few years earlier, with Jack Dorsey shortly after he had been kicked out (for the first time) of his nascent start-up, Twitter. We ate Korean chicken wings and drank draft beer at a place on 8th Street, in Greenwich Village, not because Dorsey was being modest but rather because he was close to broke. It wasn’t dissimilar from my encounter with another fledgling entrepreneur, whom a friend had introduced to me at Burning Man as “Travis.” As we strolled across the sandy playa, with techno music bleating through the air, I was told that Travis Kalanick worked “for a new start-up called Uber.”

In Silicon Valley, things happen fast. Uber is now worth $68 billion. Dorsey runs two public companies and sits on the board of Disney. Kevin Systrom sold Instagram to Facebook for $1 billion. And just four years after Spiegel fretted to me about his midterm, his start-up, Snapchat, is valued at $18 billion. Perhaps more profoundly, however, these young men, and so many more of their ilk, have come to rule our world in increasingly consequential ways. They control the platforms—how we view the birth of a newborn, how we learn about the blunders of a politician, or how we get to work—that control our lives.

From a business perspective, this new generation of technology moguls rival the Fords and Rockefellers of previous eras. Social networks alone are more valuable than the G.D.P. of more than 95 percent of the countries around the globe. And yet I often think back to those kids I sat across from and wonder whether they are really prepared to be making the kinds of decisions that shape the world and affect our future.

From their actions, it would seem that the answer is no. For a time, when terrorists used Twitter to recruit members, the company’s leaders would often just throw their hands in the air. When taxi drivers lose their jobs as a result of ride-sharing apps, or a driver bludgeons a passenger with a hammer, that may just be the collateral damage of Uber’s massive growth.

For those who follow the Valley, this isn’t all that surprising. Perhaps the most influential figure in the industry, after all, isn’t Steve Jobs or Sheryl Sandberg, but rather Ayn Rand. Jobs’s co-founder, Steve Wozniak, has suggested that Atlas Shrugged was one of Jobs’s “guides in life.” For a time, Kalanick’s Twitter avatar featured the cover of The Fountainhead. Peter Thiel, whose dissatisfaction with a Gawker story led him to underwrite a lawsuit that eventually killed off the site, and who made the outré decision to publicly support Donald Trump, is also a self-described Rand devotee.

At their core, Rand’s philosophies suggest that it’s O.K. to be selfish, greedy, and self-interested, especially in business, and that a win-at-all-costs mentality is just the price of changing the norms of society. As one start-up founder recently told me, “They should retitle her books It’s O.K. to Be a Sociopath!” And yet most tech entrepreneurs and engineers appear to live by one of Rand’s defining mantras: The question isn’t who is going to let me; it’s who is going to stop me.

This year, Vanity Fair has combined the two disparate lists of the New Establishment—“The Disrupters,” dedicated to Silicon Valley upstarts, and “The Powers That Be,” largely a locus of New York and L.A. moguls—into one comprehensive catalogue of modern power and influence. That’s because, on some level, everyone is now in the technology business. Put another way, every person on this list is competing with every other person, often for the same thing: our time. Jeff Bezos may have started out wanting to sell books, but now Amazon is contending with Hollywood, FedEx, and Apple in the entertainment, logistics, and streaming businesses. Kalanick may have initially wanted to make it easier to find a cab, but now Uber is competing in the self-driving-car industry against not only G.M., Chrysler, and Ford but also Tesla and Google, among many others. Spiegel started Snapchat to facilitate the act of sending risqué messages. Four years later his company is a legitimate threat to the entire future of television.

“THEY SHOULD RETITLE HER BOOKS IT’S O.K. TO BE A SOCIOPATH!”

The people who are building our futures are fully aware of this new, hyper-accelerated world—a landscape where everyone is a competitor with everyone else and even billion-dollar ideas can be ephemeral. Walk through Facebook’s headquarters and you will see that famous white poster with red lettering that says, “Move fast and break things,” the much-professed credo of its founder. But something is lost when we travel at such high velocities. I remember once overhearing, in a San Francisco coffee shop, a 19-year-old start-up founder callously offer advice to an 18-year-old founder about how to fire an engineer. It makes me wonder, Who are these young entrepreneurs learning from? Who is teaching them that when they press a button on their keyboard, millions, or even billions, of people can be affected, sometimes in terrifying ways? Is Ayn Rand their only guiding light? One hopes that some of these young moguls, or those who aspire to be them, will take a cue from some of the other members of this list, who worked their way to the top over the course of decades. Spiegel hadn’t even yet come up with the notion of Snapchat when Bob Iger forged the successful relationships with Pixar and Lucasfilm that have made him among the most successful media executives of his, or any, era. I don’t think he was worried about who was going to stop him.

There’s a saying in tech that “the future ages quickly.” When the iPhone came out, we all drooled with delight at the flat touch screen. But it didn’t take long for people to complain that it wasn’t big enough. This truism will likely be reflected in how quickly the people who are currently disrupting our society will themselves be disrupted. As Spiegel and Kalanick and Zuckerberg move fast and break things, there are kids in dorm rooms at Stanford, or men and women arriving in San Francisco, who want to move faster and break bigger things, too. In some ways, our future hinges on what they learned from their predecessors.

To view the complete 2016 V.F. New Establishment List, go here.

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Silicon Valley’s 14 Most Spectacular Failures
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Andrew Mason, Groupon

Andrew Mason, Groupon

Scorned as the “worst C.E.O. of 2012” by CNBC’s Herb Greenberg, Andrew Mason was at the helm of Groupon when the company went public, an I.P.O. Greenberg wrote off as the “most over-hyped . . . of recent years.” Years after going public, Groupon still has trouble turning a profit.
Photo-Illustration by Ben Park; From Bloomberg (Mason), Robert Kirk/Photodisc (Ticket), both from Getty Images.
Elizabeth Holmes, Theranos

Elizabeth Holmes, Theranos

Elizabeth Holmes became emblematic of Silicon Valley excess when her $9 billion blood-testing start-up, Theranos, became the subject of a series of Wall Street Journal investigations that reported that the company’s technology didn’t actually work. Theranos is currently under federal criminal investigation.
Photo-Illustration by Ben Park; By Adrianna Williams/The Image Bank (Needle), Andrew Burton (Holmes), both from Getty Images.
Parker Conrad, Zenefits

Parker Conrad, Zenefits

Zenefits C.E.O. and co-founder Parker Conrad resigned in 2016 amid concerns over questions about his $4.5 billion start-up’s regulatory compliance. Further reports insinuated Zenefits’ company culture under Conrad was more frat house than hackathon, complete with allegations of sex in the stairwells and plenty of drinking.
Photo-Illustration by Ben Park; By Steve Jennings (Conrad), Jack Andersen/DigitalVision (Beer), both from Getty Images.
Marissa Mayer, Yahoo

Marissa Mayer, Yahoo

Hailed as the turnaround boss Yahoo so desperately needed when she was hired for the job in 2012, Marissa Mayer has come under fire as investors have lost their patience waiting for a miracle that never came. (The millions she reportedly spent on lavish parties and perks, while the ailing Internet giant circled the drain, didn’t help.) Yahoo is now up for sale.
Photo-Illustration by Ben Park; By Robyn Beck/AFP/Getty Images (Mayer).
David Byttow, Secret

David Byttow, Secret

David Byttow, the founder of anonymous-posting app Secret, pivoted his year-old start-up to an incubator in 2015 after allegedly pocketing millions and buying a flashy Ferrari. Google Ventures investor Bill Maris later compared the start-up shutting down to a “bank heist.”
Photo-Illustration by Ben Park; By Car Culture (Ferrari), Heather Kennedy (Byttow), both from Getty Images.
Michelle Peluso, Gilt

Michelle Peluso, Gilt

Gilt Groupe, the once hot flash-sales start-up, was valued at $1 billion in 2011, having raised more than $286 million in funding since its founding. Five years later, Hudson’s Bay, the parent company of Saks Fifth Avenue, purchased it for $250 million in what CNN dubbed the “ultimate flash sale.”
Photo-Illustration by Ben Park; From Bloomberg Finance LP (Peluso), Rastem Grler (Sign), both from Getty Images.
Anthony Bay, Rdio

Anthony Bay, Rdio

Rdio filed for bankruptcy in 2015, showing just how hard it can be to make a viable streaming service. Rdio had raised $125 million in funding at a $500 million valuation. Pandora scooped up “many employees” from the failed start-up afterward, though its C.E.O. Anthony Bay did not join them.
Photo-Illustration by Ben Park; From Bloomberg Finance LP/Getty Images (Bay); From Alamy (Headphones).
Dan Wagner, Powa Technologies

Dan Wagner, Powa Technologies

C.E.O. Dan Wagner said that his company’s product, a glorified Q.R. scanner called PowaTag, was going to help Powa become “the greatest technology company of all time.” In February, $2.7 billion Powa shut down after struggling with its flagship product and, according to former employees, Wagner’s own hubris.
Photo-Illustration by Ben Park; From Bloomberg/Getty Images (Wagner).
Adora Cheung, Homejoy

Adora Cheung, Homejoy

On-demand cleaning start-up Homejoy shut down in 2015 after failing to hold onto its customers. C.E.O. Adora Cheung reportedly didn’t work to fix its retention rates, which flopped as a result of offering $19 flat-fee introductory deals. The “deciding factors” in Homejoy closing its doors, however, were the four lawsuits it faced from workers who claimed they’d been misclassified as contractors. The lawsuits were still pending as of last summer.
Photo-Illustration by Ben Park; By Anthony Harvey (Cheung), Tim Macpherson/Cultura (House), both from Getty Images.
Ben Kaufman, Quirky

Ben Kaufman, Quirky

Quirky, a start-up that sought to crowdsource inventions to the masses, filed for bankruptcy in September 2015. Quirky struggled to raise funding and C.E.O. Ben Kaufman stepped down a month before his company folded. Quirky sold Wink, its software business, to Flextronics for $15 million.
Photo-Illustration by Ben Park; By Larry Busacca/Getty images (Kaufman).
Scott Thompson, Yahoo

Scott Thompson, Yahoo

Scott Thompson served as C.E.O. of Yahoo before the company hired Marissa Mayer. Months after Thompson was hired to the job, vocal activist investor Dan Loeb sent Yahoo’s board a letter questioning Thompson’s credentials and wondering if perhaps Thompson had “embellished his academic credentials.” Thompson was immediately replaced with Ross Levinsohn, after the board discovered Thompson had falsely added a computer-science degree to his résumé.
Photo-Illustration by Ben Park; By Jo Foord (Kindersley), from Bloomberg (Thompson), both from Getty Images.
Carly Fiorina, H.P.

Carly Fiorina, H.P.

When Carly Fiorina was let go from her six-year tenure as C.E.O. of Hewlett-Packard, the company’s stock jumped 10 percent upon the news of her firing. While she was C.E.O., Fiorina didn’t increase the company’s profits, and she actually decreased H.P.’s shareholders’ wealth by 52 percent. A disastrous merger with Compaq, which led her to fire some 30,000 employees, haunted Fiorina throughout her failed senate and presidential campaigns, too.
Digital Colorization by Ben Park; By Justin Sullivan/Getty Images. (Fiorina).
Jason Goldberg, Fab

Jason Goldberg, Fab

E-commerce start-up Fab was once valued at $900 million, a near unicorn in Silicon Valley terms. But after allegedly burning through $200 million of its $336 million in venture capital, C.E.O. Jason Goldberg was forced to shutter its European arm and lay off two-thirds of its staff.
Photo-Illustration by Ben Park; By Anthony Harvey (Goldberg), Oli Scarff (Frame), both from Getty Images.
Gurbaksh Chahal, RadiumOne and Gravity4

Gurbaksh Chahal, RadiumOne and Gravity4

Fired in 2014 from his ad-tech firm RadiumOne following a domestic-violence conviction, Gurbaksh Chahal founded a new company to compete with the one he was kicked out of. But Gravity4, his new firm, was sued for gender discrimination in 2015, though that case is still pending, and former employees have contemplated legal action against him.
Photo-Illustration By Ben Park; By Charley Gallay/Getty Images (Chahal).
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Nick Bilton Nick Bilton is a special correspondent for Vanity Fair.

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