“Oh My God, This Is So F—ed Up”: Inside Silicon Valley’s Dark Side

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“Oh My God, This Is So F—ed Up”: Inside Silicon Valley’s Dark Side

Nervous, she dipped her finger into the powder and put it in her mouth. Soon, her guard dropped. Then, the male founder asked if he could kiss her. “It was so weird,” she says. “I’m like, ‘Your wife is right there; is she O.K. with this?’ ” The founder’s wife acknowledged that, yes, she was O.K. with it. Jane Doe, who considers herself fairly adventurous and open-minded, kissed the founder, then became uncomfortable, feeling as if she had been pressured or targeted. “I don’t know what I’m doing, I feel really stupid, I’m drugged up because I’d never taken it before, and he knew I’d never taken it,” she recalled. She tried to escape to a different area of the party. “I felt gross because I had participated in making out with him and then he kept trying to find me and I kept trying to run away and hide. I remember saying to him, ‘Aren’t people going to wonder?’ And he said, ‘The people that know me know what is going on, and the people that don’t, I don’t really care.’ ” Before dawn, she jumped into her car and left. “What’s not O.K. about this scene is that it is so money- and power-dominated. It’s a problem because it’s an abuse of power. I would never do it again.”

While this particular woman felt ambushed, if it’s your first time, a friend will normally fill you in on what you’re signing up for, and you are expected to keep it to yourself. You know that if you do drugs with someone you work with you shouldn’t mention it to anyone, and the same goes with sex. In other words, we’re not hiding anything, but, actually, we kind of are. You only get invited if you can be trusted and if you’re going to play ball. “You can choose not to hook up with [a specific] someone, but you can’t not hook up with anybody, because that would be voyeurism. So if you don’t participate, don’t come in,” says one frequent attendee, whom I’ll call Founder X, an ambitious, world-traveling entrepreneur.

They don’t necessarily see themselves as predatory. When they look in the mirror, they see individuals setting a new paradigm of behavior by pushing the boundaries of social mores and values. “What’s making this possible is the same progressiveness and open-mindedness that allows us to be creative and disruptive about ideas,” Founder X told me. When I asked him about Jane Doe’s experience, he said, “This is a private party where powerful people want to get together and there are a lot of women and a lot of people who are fucked up. At any party, there can be a situation where people cross the line. Somebody fucked up, somebody crossed the line, but that’s not an indictment on the cuddle puddle; that’s an indictment on crossing the line. Doesn’t that happen everywhere?” It’s worth asking, however, if these sexual adventurers are so progressive, why do these parties seem to lean so heavily toward male-heterosexual fantasies? Women are often expected to be involved in threesomes that include other women; male gay and bisexual behavior is conspicuously absent. “Oddly, it’s completely unthinkable that guys would be bisexual or curious,” says one V.C. who attends and is married (I’ll call him Married V.C.). “It’s a total double standard.” In other words, at these parties men don’t make out with other men. And, outside of the new types of drugs, these stories might have come out of the Playboy Mansion circa 1972.

I had a wide-ranging conversation with Twitter co-founder Evan Williams about the peculiar mixture of audacity, eccentricity, and wealth that swirls in Silicon Valley. Williams, who is married with two kids, became an Internet celebrity thanks to his first company, Blogger. He pointed out that he was never single, well known, and rich at the same time, and that he isn’t part of this scene, but recognizes the motivations of his peers. “This is a strange place that has created incredible things in the world and therefore attracts these types of people and enables these types of people. How could it be anything but weird and dramatic and people on the edge testing everything?” On the one hand, he said, “if you thought like everyone else, you can’t invent the future,” yet he also warned that, sometimes, this is a “recipe for disaster.”

Rich men expecting casual sexual access to women is anything but a new paradigm. But many of the A-listers in Silicon Valley have something unique in common: a lonely adolescence devoid of contact with the opposite sex. Married V.C. described his teenage life as years of playing computer games and not going on a date until he was 20 years old. Now, to his amazement, he finds himself in a circle of trusted and adventurous tech friends with the money and resources to explore their every desire. After years of restriction and longing, he is living a fantasy, and his wife is right there along with him.

Married V.C.’s story—that his current voraciousness is explained by his sexual deprivation in adolescence—is one I hear a lot in Silicon Valley. They are finally getting theirs.

Founder Hounders

There is an often told story that Silicon Valley is filled with women looking to cash in by marrying wealthy tech moguls. Whether there really is a significant number of such women is debatable. The story about them is alive and well, however, at least among the wealthy men who fear they might fall victim. In fact, these guys even have a term for the women who pursue them: founder hounders.

When I ask Founder X whether these men are taking advantage of women by feeding them inhibition-melting drugs at sex parties, he replies that, on the contrary, it’s women who are taking advantage of him and his tribe, preying on them for their money.

On their way up to a potential multi-million-dollar payout, some younger founders report, more and more women seem to become mysteriously attracted to them no matter how awkward, uncool, or un­at­trac­tive they may be.

However many founder hounders exist, the idea of these women lives large in the minds of Silicon Valley founders, who often trade stories about women they’ve dated. As Founder X puts it, “We’ll say whether some girl is a fucking gold digger or not, so we know who to avoid.”

When I tell her this, Ava, a young female entrepreneur, rolls her eyes. According to Ava, who asked me to disguise her real identity and has dated several founders, it’s the men, not the women, who seem obsessed with displays of wealth and privilege. She tells of being flown to exotic locations, put up in fancy hotels, and other ways rich men have used their money to woo her. Backing up Ava’s view are the profiles one finds on dating apps where men routinely brag about their tech jobs or start-ups. In their online profiles, men are all but saying, “Hello, would you like to come up to my loft and see my stock options?”

In Ava’s experience, however, once men like this land a woman, they are quick to throw her back. After a few extravagant dates, Ava says, she will initiate a conversation about where the tryst is going. The men then end things, several using the same explanation. “They say, ‘I’m still catching up. I lost my virginity when I was 25,’ ” Ava tells me. “And I’ll say, ‘Well, you’re 33 now, are we all caught up yet?’ In any other context, [these fancy dates] would be romantic, but instead it’s charged because no one would fuck them in high school. . . . I honestly think what they want is a do-over because women wouldn’t bone them until now.”

Ava’s jaundiced view of newly wealthy moguls would be funny if their gold-digger obsession didn’t mask something serious. The claim of being stalked by women often becomes an excuse used by some tech stars to justify their own predatory behavior.

What that adds up to is a great deal of ego at play. “It’s awesome,” says Founder X. At work, he explains, “you’re well funded. You have relative traction.” Outside work, “why do I have to compromise? Why do I have to get married? Why do I have to be exclusive? If you’ve got a couple girls interested in you, you can set the terms and say, ‘This is what I want.’ You can say, ‘I’m happy to date you, but I’m not exclusive.’ These are becoming table stakes for guys who couldn’t get a girl in high school.”

Furthermore, these elite founders, C.E.O.’s, and V.C.’s see themselves as more influential than most hot-shit bankers, actors, and athletes will ever be. “We have more cachet than a random rich dude because we make products that touch a lot of people,” says Founder X. “You make a movie, and people watch it for a weekend. You make a product, and it touches people’s lives for years.”

At least on the financial level, Founder X has a point. The payouts of A-list actors and the wolves of Wall Street just aren’t that impressive among the Silicon Valley elite. Managing directors at top-tier investment banks may pocket a million a year and be worth tens of millions after a long career. Early employees at tech firms like Uber, Airbnb, and Snapchat can make many times that amount of money in a matter of years. Celebrities such as Ashton Kutcher, Jared Leto, and Leonardo DiCaprio have jumped on that power train and now make personal investments in tech companies. The basketball great Kobe Bryant started his own venture-capital firm. LeBron James has rebranded himself as not just an athlete but also an investor and entrepreneur.


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“Oh My God, This Is So F—ed Up”: Inside Silicon Valley’s Dark Side

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