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

Some of the most powerful men in Silicon Valley are regulars at exclusive, drug-fueled, sex-laced parties—gatherings they describe not as scandalous, or even secret, but as a bold, unconventional lifestyle choice. Yet, while the guys get laid, the women get screwed. In an adaptation from her new book, Brotopia, Emily Chang exposes the tired and toxic dynamic at play.

by

• Emily Chang

January 2, 2018,https://www.vanityfair.com/news/2018/01/brotopia-silicon-valley-secretive-orgiastic-inner-sanctum

Photo Illustration by Darrow.

About once a month, on a Friday or Saturday night, the Silicon Valley Technorati gather for a drug-heavy, sex-heavy party. Sometimes the venue is an epic mansion in San Francisco’s Pacific Heights; sometimes it’s a lavish home in the foothills of Atherton or Hillsborough. On special occasions, the guests will travel north to someone’s château in Napa Valley or to a private beachfront property in Malibu or to a boat off the coast of Ibiza, and the bacchanal will last an entire weekend. The places change, but many of the players and the purpose remain the same.

The stories I’ve been told by nearly two dozen people who have attended these events or have intimate knowledge of them are remarkable in a number of ways. Many participants don’t seem the least bit embarrassed, much less ashamed. On the contrary, they speak proudly about how they’re overturning traditions and paradigms in their private lives, just as they do in the technology world they rule. Like Julian Assange denouncing the nation-state, industry hotshots speak of these activities in a tone that is at once self-congratulatory and dismissive of criticism. Their behavior at these high-end parties is an extension of the progressiveness and open-mindedness—the audacity, if you will—that make founders think they can change the world. And they believe that their entitlement to disrupt doesn’t stop at technology; it extends to society as well. Few participants, however, have been willing to describe these scenes to me without a guarantee of anonymity.

If this were just confined to personal lives it would be one thing. But what happens at these sex parties—and in open relationships—unfortunately, doesn’t stay there. The freewheeling sex lives pursued by men in tech—from the elite down to the rank and file—have consequences for how business gets done in Silicon Valley.

Sex Parties of the Tech and Famous

From reports of those who have attended these parties, guests and hosts include powerful first-round investors, well-known entrepreneurs, and top executives. Some of them are the titans of the Valley, household names. The female guests have different qualifications. If you are attractive, willing, and (usually) young, you needn’t worry about your résumé or bank account. Some of the women work in tech in the Bay Area, but others come from Los Angeles and beyond, and are employed in symbiotic industries such as real estate, personal training, and public relations. In some scenarios, the ratio of women to wealthy men is roughly two to one, so the men have more than enough women to choose from. “You know when it’s that kind of party,” one male tech investor told me. “At normal tech parties, there are hardly any women. At these kinds of party, there are tons of them.”

I believe there is a critical story to tell about how the women who participate in these events are often marginalized, even if they attend of their own volition. One female investor who had heard of these parties before I approached her told me, “Women are participating in this culture to improve their lives. They are an underclass in Silicon Valley.” A male investor who works for one of the most powerful men in tech put it this way: “I see a lot of men leading people on, sleeping with a dozen women at the same time. But if each of the dozen women doesn’t care, is there any crime committed? You could say it’s disgusting but not illegal—it just perpetuates a culture that keeps women down.”

To be clear, there is a wide range of parties for experimental sexual behavior. Some, devoted entirely to sex, may be drug- and alcohol-free (to encourage safety and performance) and demand a balanced gender ratio. Others are very heavy on drugs and women and usually end in group “cuddle puddles,” a gateway to ever-so-slightly more discreet sexual encounters.

Men show up only if directly invited by the host, and they can often bring as many women as they want, but guys can’t come along as plus-ones. (That would upset the preferred gender ratio.) Invitations are shared via word of mouth, Facebook, Snapchat (perfect, because messages soon disappear), or even basic Paperless Post. Nothing in the wording screams “sex party” or “cuddle puddle,” in case the invitation gets forwarded or someone takes a screenshot. Besides, there’s no need to spell things out; the guests on the list understand just what kind of party this is. Women too will spread the word among their female friends, and the expectations are hardly hidden. “They might say, ‘Do you want to come to this really exclusive hot party? The theme is bondage,’ ” one female entrepreneur told me. “ ‘It’s at this V.C. or founder’s house and he asked me to invite you.’ ”

“IT’S VERY RISKY—ONCE YOU’RE IN THAT CIRCLE, ONCE YOU DECIDE YOU WANT TO PLAY THE GAME, YOU CAN’T BACK OUT.”

Perhaps this culture is just one of the many offshoots of the sexually progressive Bay Area, which gave rise to the desert festival of free expression Burning Man, now frequented by the tech elite. Still, the vast majority of people in Silicon Valley have no idea these kinds of sex parties are happening at all. If you’re reading this and shaking your head saying, “This isn’t the Silicon Valley that I know,” you may not be a rich and edgy male founder or investor, or a female in tech in her 20s. And you might not understand, anyway. “Anyone else who is on the outside would be looking at this and saying, Oh my God, this is so fucked up,” one female entrepreneur told me. “But the people in it have a very different perception about what’s going on.”

This is how the night goes down, according to those who have attended. Guests arrive before dinner and are checked in by private security guards, who will turn you away if you’re not on the list. Sometimes the evening is catered. But at the most intimate gatherings, guests will cook dinner together; that way they don’t have to kick out the help after dessert. Alcohol lubricates the conversation until, after the final course, the drugs roll out. Some form of MDMA, a.k.a. Ecstasy or Molly, known for transforming relative strangers into extremely affectionate friends, is de rigueur, including Molly tablets that have been molded into the logos of some of the hottest tech companies. Some refer to these parties as “E-parties.”

MDMA is a powerful and long-lasting drug whose one-two punch of euphoria and manic energy can keep you rolling for three or four hours. As dopamine fires, connections spark around the room, and normal inhibitions drop away. People start cuddling and making out. These aren’t group orgies, per se, but guests will break out into twosomes or threesomes or more. They may disappear into one of the venue’s many rooms, or they may simply get down in the open. Night turns to day, and the group reconvenes for breakfast, after which some may have intercourse again. Eat, drugs, sex, repeat.

These sex parties happen so often among the premier V.C. and founder crowd that this isn’t a scandal or even really a secret, I’ve been told; it’s a lifestyle choice. This isn’t Prohibition or the McCarthy era, people remind me; it’s Silicon Valley in the 21st century. No one has been forced to attend, and they’re not hiding anything, not even if they’re married or in a committed relationship. They’re just being discreet in the real world. Many guests are invited as couples—husbands and wives, boyfriends and girlfriends—because open relationships are the new normal.

While some parties may be devoted primarily to drugs and sexual activity, others may boast just pockets of it, and some guests can be caught unawares. In June 2017, one young woman—let’s call her Jane Doe—received a Paperless Post invite for “a party on the edge of the earth” at the home of a wealthy venture capitalist. The invite requested “glamazon adventurer, safari chic and jungle tribal attire.” Ironically, the gathering was held just a week after sexual-harassment allegations against Binary Capital co-founder Justin Caldbeck had been reported, but that didn’t seem to discourage certain guests from indulging in heavy petting in the open.

“It was in the middle of the Binary thing,” Jane Doe told me, referring to the scandal at the V.C. firm. “And it was all so ridiculous.” Doe found herself on the floor with two couples, including a male entrepreneur and his wife. The living room had been blanketed in plush white faux fur and pillows, where, as the evening wore on, several people lay down and started stroking one another, Doe said, in what became a sizable cuddle puddle. One venture capitalist, dressed up as a bunny (it’s unclear how this fit into the edge-of-the-earth theme), offered Jane Doe some powder in a plastic bag. It was Molly. “They said it will just make you feel relaxed and you’re going to like being touched,” Doe recounted to me.

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.

With famous actors and athletes wanting to get into the tech game, it’s no surprise that some in the Valley have a high opinion of their attractiveness and what they should expect or deserve in terms of their sex lives. In the Valley, this expectation is often passed off as enlightened—a contribution to the evolution of human behavior.

For many women who describe it, however, it’s a new immaturity—sexist behavior dressed up with a lot of highfalutin talk—that reinforces traditional power structures, demeans women, and boosts some of the biggest male egos in history: just another manifestation of Brotopia.

When I spoke about Silicon Valley’s sex parties—specifically those where women vastly outnumber men—with Elisabeth Sheff, a Chattanooga-based writer and professor who has spent two dec­ades researching open relationships, her reaction was heated: “That’s exploitation. That’s old-school, fucked-up masculine arrogance and borderline prostitution,” she said. “The men don’t have to prostitute themselves, because they have the money. . . . ‘I should be able to have sex with a woman because I’m a rich guy.’ That is not even one particle progressive; that is the same tired bullshit. It’s trying to blend the new and keeping the old attitudes, and those old attitudes are based in patriarchy, so they come at the expense of women.”

Jennifer Russell, who runs the established Camp Mystic at Burning Man, is more sympathetic. “Men and women are equally drawn to creating a structure that invites their full sexual expression, and events like this are a safe place to dabble,” she says. “It’s way better than a swingers’ club would feel because this is at a home and you are surrounded by people you know.”

Married V.C. admits, however, that for many men these parties aren’t so much about self-expression as they are about simply sport fucking. “Some guys will whip out their phones and show off the trophy gallery of girls they’ve hooked up with,” he says. “Maybe this is behavior that happened on Wall Street all the time, but in a way they owned it. These founders do this, but try not to own it. They talk about diversity on one side of their mouth, but on the other side they say all of this shit.”

The New Paradigm for Women Getting Screwed

For successful women in Silicon Valley, the drug-and-sex-party scene is a minefield to navigate. This isn’t a matter of Bay Area tech women being more prudish than most; I doubt recent history has ever seen a cohort of women more adventurous or less restrained in exploring sexual boundaries. The problem is that the culture of sexual adventurism now permeating Silicon Valley tends to be more consequential for women than for men, particularly as it relates to their careers in tech.

Take multi-time entrepreneur Esther Crawford, who is familiar with sex parties (specifically those with an equal gender ratio and strict rules around consent) and talks openly about her sexual experiments and open relationships. For four years, she had been in a non-monogamous (they say “monogamish”) relationship with Chris Messina, a former Google and Uber employee best known for inventing the hashtag. More recently, Crawford and Messina have started a company together called Molly—perhaps not un-coincidentally the same name as the drug—where they are developing a “nonjudgmental (artificially intelligent) friend who will support your path to more self-awareness.” They also chose to become monogamous for a while; seeing other people was getting too complicated. “The future of relationships is not just with humans but A.I. characters,” Crawford told me. By December 2017, they had raised $1.5 million for their new company. In the meantime, Crawford is acutely aware of the harsh reality that as a female entrepreneur she faces so many challenges that men don’t. What she has found is that, for a woman, pushing private sexual boundaries comes with a price.

When Crawford was raising funds for her second company, a social-media app called Glmps, she went to dinner with an angel investor at a hip restaurant on San Francisco’s Valencia Street. At the end of the meal, he handed her a check for $20,000, then immediately tried to kiss her. “I certainly wasn’t coming on to him,” she asserts. “I kind of leaned back, and he ordered me an Uber, and I was like, ‘I gotta go home.’ ” Crawford thinks it’s likely that this particular investor knew about her sexual openness and found it difficult to think of her simply as an entrepreneur rather than as a potential hookup. This encounter is an example of a unique penalty women face if they choose to participate in the “we’re all cool about sex” scene.

Ava was working as an executive assistant at Google when she ran into her married boss at a bondage club in San Francisco. He was getting a blow job from a woman strapped to a spanking bench who was being entered by another man from behind. Ava and her boss, an engineer, locked eyes but didn’t exchange a word and never spoke of the encounter again. However, a few months later, at a Google off-site event, another married male colleague approached her. “He hits on me, and I was like, What are you doing? Don’t touch me. Who are you again? He was like, I know who you are. The other guys said you like all this stuff.” Someone had outed Ava. She quit working at Google shortly thereafter. “The trust works one way,” Ava says. “The stigma for a woman to do it is so much higher. I’m supposed to be in this industry where everyone is open and accepting, but as a woman the punishment is so much more unknown.”

Crawford can’t even count the number of men who’ve told her how lucky she is to have so many eligible men to date in the male-dominated tech scene. “Of all the privileges in the world, that is not the one I would choose,” she says fiercely. “I’d choose equal pay for equal work. I’d choose having better access to capital and power. I’d choose not being passed over for promotions. I’d choose not having to worry about being in the 23.1 percent of undergraduate college women who get sexually assaulted. I’d choose not being slut-shamed if I do opt to explore my sexuality.”

Married V.C. admits he might decline to hire or fund a woman he’s come across within his sex-partying tribe. “If it’s a friend of a friend or you’ve seen them half-naked at Burning Man, all these ties come into play,” he says. “Those things do happen. It’s making San Francisco feel really small and insular because everybody’s dated everybody.” Men actually get business done at sex parties and strip clubs. But when women put themselves in these situations, they risk losing credibility and respect.

The party scene is now so pervasive that women entrepreneurs say turning down invitations relegates them to the uncool-kids’ table. “It’s very hard to create a personal connection with a male investor, and if you succeed, they become attracted to you,” one told me. “They think you’re part of their inner circle, [and] in San Francisco that means you’re invited to some kind of orgy. I couldn’t escape it here. Not doing it was a thing.” Rather than finding it odd that she would attend a sex party, says this entrepreneur, people would be confused about her not attending. “The fact that you don’t go is weird,” the entrepreneur said, and it means being left out of important conversations. “They talk business at these parties. They do business,” she said. “They decide things.” Ultimately, this entrepreneur got so fed up that she moved herself and her start-up to New York and left Silicon Valley for good.

The women who do say yes to these parties rarely see a big business payoff. “There is a desire to be included and invited to these kinds of things and sometimes it felt like it was productive to go and you could get ahead faster by cultivating relationships in this way,” one female tech worker told me. “Over time, I realized that it’s false advertising and it’s not something women should think is a way to get ahead. It’s very risky—once you’re in that circle, once you decide you want to play the game, you can’t back out. If you really believe that’s going to get you to a serious place in your career, that’s delusion.”

Another female entrepreneur described the unfair power dynamic that’s created. “There is this undercurrent of a feeling like you’re prostituting yourself in order to get ahead because, let’s be real, if you’re dating someone powerful, it can open doors for you. And that’s what women who make the calculation to play the game want, but they don’t know all the risks associated with it,” she said. “If you do participate in these sex parties, don’t ever think about starting a company or having someone invest in you. Those doors get shut. But if you don’t participate, you’re shut out. You’re damned if you do, damned if you don’t.”

It hearkens back to those popular 1980s teen movies which tell the “heartwarming” story of a glasses-wearing nerd who is transformed into the cool, funny kid who gets all the hot chicks. But we’re not living a teenage dream. Great companies don’t spring magically to life when a nerd gets laid three times in a row. Great companies are built in the office, with hard work put in by a team. The problem is that weekend views of women as sex pawns and founder hounders can’t help but affect weekday views of women as colleagues, entrepreneurs, and peers.

Adapted from Brotopia: Breaking Up the Boys’ Club of Silicon Valley, by Emily Chang, to be published on February 6, 2018, by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC; © 2018 by the author.

CORRECTION: A photo with incorrect caption information has been removed from the story.