ABOUT ONCE A MONTH, on a Friday or Saturday night, a select group of 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 or longer. 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 makes 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. However, few participants have been willing to describe these scenes to me without a guarantee of anonymity.
Sex parties are just one aspect—albeit an impressively excessive one—of today’s sexually open Valley culture. Everyone, it seems, is experimenting with their sexual lives and relationships. A thriving hook-up culture is fueled by apps such as Bumble and Tinder. Open relationships are common and there is an active polyamorous community. For the large population of young heterosexual men in tech making six figures, there is also the pay-for-sex scene that includes strip clubs, easy access to online escorts, and a new type of prostitution promoted by numerous “sugar daddy” websites where men pay women regular stipends for their companionship.
If this activity was just relegated to personal lives it would be one thing. But what happens at these sex parties—and in open relationships and at strip clubs as we’ll see later—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.
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, men whose faces have graced the covers of tech and business magazines. Billionaires abound. 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 local 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 parties, there are tons of them.”
Over the last two years, numerous sources have told me that this culture has become rampant, though this has been the hardest chapter of this book to report by far. Many potential sources, especially women, abruptly canceled meetings with me the day of. Others asked me not to reveal their names, fearing retribution.
Still, 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 this culture before I approached her told me, “Women are participating in these parties 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. The path by which women are lured into these sex parties differs. One female tech worker told me she fell into a high-flying, open-minded crowd after attending a party for the Bravo reality show about Silicon Valley. “I was invited to some villa in the city, I had just graduated from college, and it sounded cool and glamorous,” she said. That took her on a series of unexpected adventures, including a sex party where several tech founders and engineers were in attendance and food was being served off the bodies of naked women. A few years later, this same woman met an investor who was trying to sell off some of his shares in a multibillion-dollar start-up on the secondary market. She introduced him to prospective buyers and received a commission for her efforts. The pair started dating, and the investor took her to exclusive dinner parties, one of which ended up being a sex party. When I asked for more details, she grew quiet. Talking about these events to anyone on the outside, she said, is “seen as the ultimate betrayal.”
Men show up only if directly invited by the host, and they can 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,” just in case the invitation gets forwarded or someone takes a screen shot. No need to spell things out, anyway; 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 VC or founder’s house and he asked me to invite you.’”
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 twenties. 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. 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 designer 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 such as Tesla and Snapchat. Some refer to these parties as “E-parties.” “People ingest Molly like candy during these events,” says a woman who has partaken. Sometimes guests will mix the bitter powder with a fruity drink or stir it into a coconut.
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. “When you’re on it, you feel like you love everybody,” says one female entrepreneur. 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 high-end, premier VC 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 twenty-first 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 might 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.” The invite requested “glamazon adventurer, safari chic and jungle tribal attire” for the party, to be hosted at “Casa Jurvey by the Sea”—the home of venture capitalist Steve Jurvetson in the resort beach town of Half Moon Bay, south of San Francisco. It turned out that this was the afterparty for his venture capital firm, DFJ’s Big Think “unconference,” an exclusive gathering for folks in the tech industry. But two invites went out for the same event, a moody, provocative Paperless Post invite, tiger and all, and then a separate, official email from Jurvetson’s firm. This second invite was a straightforward email from DFJ inviting guests to a daytime retreat that included “expert-led breakout sessions” and “The Afterthought” party at Jurvetson’s home. This was just four months before he would leave the firm amid allegations of misconduct.
In photos of the party posted to a private group on Facebook, Tesla CEO Elon Musk—a longtime friend of Jurvetson’s—appears, wearing a black armorlike costume adorned with silver spikes and chains. Jurvetson is sporting a feather vest and hat. Google co-founder Sergey Brin was also there, bare-chested in a vest, as was Jonathan Teo, Justin Caldbeck’s business partner, who later referred to the party as “Magic” in a Facebook post. Ironically, the gathering was held just a week after sexual harassment allegations against Caldbeck had been reported, but that didn’t seem to discourage certain guests from participating 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 VC firm. “And it was all so ridiculous.” Doe found herself on the floor with two other 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 says, in what became a sizeable cuddle puddle. Photos reveal a group of men and women lying close together, kissing and massaging one another. In a later Facebook comment, Jurvetson referred to one snapshot of the scene as “deep cuddle.” 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 said. “I’m like, ‘Your wife is right there, is she okay with this?’” The founder’s wife acknowledged that, yes, she was okay 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 okay 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, at more private affairs, if it’s your first time, a friend might 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 get invited only 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. This is the same general spirit at play in the orgy dome at Burning Man, popular among techies. “No spectators” is the slogan out on the playa, and so it is back home.
They don’t see themselves as predatory, of course. 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 openmindedness that allowed 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 anywhere?” 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 VC who attends and is married (I’ll call him Married VC). “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.
Regardless, a select few at the very top believe it’s their obligation to tear down traditional sexual expectations. They are just expressing who they are. Founder X summed it up this way: “You build your own team and you get to build your own reality. Why wouldn’t that mentally spill over into your sexual life?”
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 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 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 VC described his teenage life as years of playing computer games and not going on a date until he was twenty 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 with him. In fact, they’ve introduced several newbies, including Founder X, to this brave new world.
Married VC’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.
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 asked Founder X whether these men are taking advantage of women by feeding them inhibition-melting drugs at sex parties, he replied 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 multimillion-dollar payout, younger founders report that more and more women seem to become mysteriously attracted to them no matter how awkward, uncool, or unattractive they may be. Alexis Ohanian, who co-founded Reddit, remembers going to bars with his co-founder, Steve Huffman, in the early days before their company was well known. They’d be proudly wearing T-shirts bearing the Reddit logo, but they had no luck with the ladies. As Reddit became more recognizable, however, the T-shirt attracted more and more attention until eventually Ohanian stopped wearing any Reddit-branded swag. In fact, when he went on dates, he would not mention Reddit at all.
“I would just try to avoid the conversation to see how long I could go before they found out where I worked,” Ohanian says. Of course, the internet makes it impossible to hide such information for long. “Fuck you, I can’t believe you founded Reddit,” one woman texted him after a few dates. Whether she was impressed or felt deceived was a little unclear. Ohanian solved this problem by marrying someone even more famous than he is: the tennis phenomenon Serena Williams.
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 have then ended things, several using the same explanation. “They say, ‘I’m still catching up. I lost my virginity when I was twenty-five,’” Ava tells me. “And I’ll say, ‘Well, you’re thirty-three 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.” His overall plan is this: “I’ll sell my company in my thirties, settle down, and have kids in my forties.”
Furthermore, these elite founders, CEOs, and VCs 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. If I’m Miranda Kerr [the very successful lingerie model], I’d think Evan Spiegel [the co-founder of Snapchat who is now Kerr’s husband] is a much more durable bet than Orlando Bloom [the actor who’s now Kerr’s ex-husband].” Bloom is only a handsome, highly paid actor, Founder X points out. That can hardly compare with Spiegel: “He’s a billionaire, and he’s got an empire.”
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.
From 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.
One clue that this is far from “evolved” behavior would be the ubiquitous drug use. “When you are on that many drugs it puts you in that mind-set where you’re not making good decisions,” one female entrepreneur told me. “At the end of the day, there are reasons why drugs are illegal. It makes you fucking crazy and after all the drug stuff is over it feels quite empty. There is a huge morality issue in Silicon Valley and at the very core, it’s people with money thinking they can get away with everything. A lot of these guys got lucky, became billionaires on paper, and so they feel they are kings of the universe. This stuff happens everywhere but at least it’s kind of shamed in New York. In Silicon Valley for some reason it’s not just okay, it’s cool.”
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 VC admits, however, that for many men, these parties aren’t so much about self-expression than 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.”
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 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 freely about her sexual experiments and open relationships. For the last four years, she has been in a nonmonogamous (they say “monogamish”) relationship with Chris Messina, a former Google and Uber employee best known for inventing the hashtag. At the time we last spoke, Crawford and Messina had decided to start a company together called Molly—perhaps not uncoincidentally the same name as the drug—a “non-judgmental, artificially intelligent friend who will support your path to more self-awareness.” They also chose to become monogamous for a while; it was getting too complicated. “The future of relationships is not just with humans but AI 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 more 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.”
While Crawford supports the idea that consenting adults should be able to form the kinds of relationships that work for them, she says, “Those who are in positions of power need to be a lot more thoughtful about how and who they engage with in their free time. It’s such a small ecosystem, and the power dynamics between VCs and founders adds a layer of complexity that everyone has to be aware of. It’s never okay for a VC to flirt with or proposition a female founder—or a female colleague for that matter!”
Married VC 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.
Women can eschew the party scene, of course, but those who do end up running a different risk. That’s what Lisa Yu discovered when she started her first company, OfficeBook, with the aim of becoming the Airbnb of office space. Just after she launched, she was invited to a penthouse party hosted by a powerful angel investor who had made his fortune as an early employee at eBay. There she met a wealthy investor. “He was super friendly and he was listening to my idea and he was like, ‘Wow, I want to connect you to my business partner.’” She says he then flashed her a few pictures of his own mansion and his yacht, where, he bragged, he hosted parties of his own. Yu dismissed the yacht photos as unsubtle self-promotion and focused instead on the suggestion that he might provide some value to her company: “I’m thinking, ‘Wow, this could actually be a business partnership.’”
The next day, Yu says she received a text from the investor inviting her to dinner on his boat. “I’m like, okay, this is odd,” Yu says. “I politely declined and he brushed it off, like ‘no worries.’” But the investor apparently wasn’t as cool about the rejection as he wanted to seem. A few days later, Yu attended a birthday party for investor Jonathan Teo. For Yu, it was an opportunity to meet new potential backers and hang out with her female founder friends; then she ran into Yacht Guy again. “I was like, ‘Oh, crap,’” Yu recalls. She managed to avoid him until the end of the night, when he cornered her and started yelling, claiming that she had missed out on a business opportunity by rejecting his earlier invitation. Yu said she was petrified. “I felt attacked and I was scared. When a drunk man is yelling at you and cornering you, what do you do?”
A girlfriend cut in between them, saying, “Are you interested in Lisa or her business? Because you’re making it very confusing.” Yacht Guy then unsubtly pivoted, trying to persuade both of them to attend that night’s afterparty. “I’m just imagining what’s happening at the mansion—drugs and orgies,” Yu tells me. “We are like, okay, we are getting out of here.”
At home, she says, “I stayed up crying and talking and eating ramen until 3:00 a.m. I just felt so defeated I almost wanted to give up on my business. If this is what it takes to start a business, I don’t know if I want to do this.” Meeting tech investors requires a certain amount of socializing, but this kind of interaction is not what she signed up for. “If you go to these parties, you’re just asking to be objectified. Sometimes you don’t even know what you’re getting yourself into. You don’t know: Is it going to be shady or not?”
Rather than give up, Yu paused her fund-raising conversations and focused on building her business organically. “I went into grind mode. I focused on customers, and within a few months we were profitable,” she says proudly. She knows the stronger her business is, the more money she can raise on her own terms, which means no need for shady investor parties. “They invite me to these things . . . but I refuse to go because I know what happens,” Yu says.
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, said 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.”
For women in Silicon Valley, if you aren’t at these weekend bacchanals, you’re missing out on potentially useful connections, not to mention being marginalized as prudish and uncool. If you are there, you’re gossiped about and reduced to a notch on a bedpost. Meanwhile, the powerful men who claim to be overturning the establishment are instead becoming age-old examples of the worst of it, shaming women for the very same behavior they give themselves and their buddies a pass for. They might as well be sad imitations of Don Draper and Roger Sterling, sniggering over martinis about the secretaries they’ve shagged. They’re not expanding boundaries, no matter how many times they go to Burning Man or how many drugs they take. Whether they were nerds or not in their teen years, they’ve now become the worst stereotype of the jock, frat boy, and banker they dismissed.
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.
Remember Susan Fowler, the former Uber engineer who blogged that her manager brought up his nonmonogamous relationship as a way to make a pass at her over the internal company chat system? It’s worth repeating what she wrote in her viral essay: “He was in an open relationship, he said, and his girlfriend was having an easy time finding new partners but he wasn’t.” Open and polyamorous relationships—like the one Fowler’s manager described—are on the rise among many tech workers in Silicon Valley but not working out to everyone’s satisfaction. As Fowler experienced, this new landscape of nonmonogamous dating can infect the workplace with varying results. Uber’s response seemed to suggest that the manager’s invitation to be part of his open sex life was not a big deal. The company, according to Fowler, told her that it “wouldn’t be comfortable punishing [the manager] for what was probably just an innocent mistake.”
That tepid response from HR may not be surprising, given that open relationships were being explored at the highest levels of the Uber organization. At the time, then-CEO Travis Kalanick was dating Gabi Holzwarth, a violinist. Holzwarth entered the Silicon Valley scene when Uber investor Shervin Pishevar hired her to play at a fundraiser at his home for soon-to-be senator Cory Booker in 2013. That’s where Holzwarth first met Kalanick. Sparks flew—but what she says she didn’t realize is that Kalanick didn’t want a traditional relationship.
Over a year after the pair broke up, Holzwarth shared with me details of their years together, including moments when Kalanick mixed business with pleasure. She shed light on a story that originally broke in The Information of the night when Kalanick joined a group of Uber executives that included the company’s head of business, Emil Michael, on a visit to an escort-karaoke bar in Seoul. “The girls were sitting in the center of this ring, shivering in miniskirts,” Holzwarth recalled. Each woman had a numbered tag so they could be chosen by the men in the group for a more personal encounter. A female Uber executive who was also in the group at the time later reported it to HR and said the incident made her “feel horrible.”
Holzwarth said that Michael called her to ask her not to discuss the night publicly—although Michael has countered that he was only calling “to let her know that reporters may try to contact her directly,” as a series of post-Fowler stories about Uber began to break in the news. Feeling he was trying to bully her into silence, she instead became the whistle-blower. It was not the only story she told. In October 2017, she posted on Facebook: “For all the women who are trying to fit in . . . you don’t have to hunt for women to bring back for them to fool around with. No, you don’t have to rate other women’s bodies, call them too ugly or fat to hang around with. No, you don’t have to sit around as you hear them compare the number of women they have slept with at one time.” When I called Holzwarth to ask what she was referring to, she said that Kalanick regularly encouraged her to find other women to bring into threesomes. She also told me that Kalanick and Michael talked openly in her presence about their sexual adventures. “Travis surrounded himself with men who liked that lifestyle; it was easier for them to get close to him,” Holzwarth told me.
A company culture is formed by what people at that company actually say and do together—the norms, standards, and values they collectively uphold. When the two most senior and important leaders of a company are a party to women being treated as objects—as Kalanick and Michael were in that bar in Seoul—it is not hard to imagine how this might poison company culture and lead cases like Susan Fowler’s to be overlooked. Again, an external investigation documented forty-seven claims of sexual harassment at Uber.
I reached out to Emil Michael about five months after he had left Uber, on the heels of Holder’s investigation. In a statement, he was both defensive and apologetic, clearly affected by the public reaction to Uber’s cultural unraveling and his role in it. He told me that he worked hard to build a diverse team, including women, at Uber, and said he deeply regretted “attending and failing to prevent” the visit to the South Korean bar. “My lack of judgment on that evening did not represent [my] values,” he told me. “I have learned a lot since those early days about the obligations that I and all leaders have to lead by example in situations like this and the lasting impact that decisions, both good and bad, can have on any organization.”
• • •
THE SPECTRUM OF OPEN relationships in Silicon Valley is broad. “Polyamory,” on one extreme, is defined as the state of being in love with, or romantically involved with, more than one person at the same time. Polyamory shares the same Latin root as “polygamy,” the practice of having more than one mate at the same time. But while polygamy is generally rejected in the Western world, polyamory has become a widely accepted social trend, at least in the Bay Area. There are no hard numbers on how many local residents have adopted, often loosely, the tenets of polyamory, but experts I’ve talked to feel safe to say that a significant majority of those who do are tech workers.
Sociologist Elisabeth Sheff has been studying polyamory since long before it was trendy in Silicon Valley. She says that most polyamorists, nationwide, are highly educated, middle- and upper-middle-class white people who have the freedom to experiment and the means to hire a good lawyer if things end badly. “In the tech industry, specifically, I think people think a lot about what is possible,” Sheff says. “If your mind is constantly like, ‘Things don’t have to be this way’ or ‘It could be any way at all, let me think of a new way,’ then you also start questioning not just binary code but binary relationships, heterosexual relationships, and marriage.”
“Polyamory is a hack,” says Twitter co-founder Evan Williams (to be clear, not his kind of hack). “It’s trying to solve the problem of love and security and excitement and novelty. It’s popular here because people see it as a smarter way to live.”
Candace Locklear is a partner at the tech public relations firm Mighty, which counts Facebook, Twitter, and Pandora among its clients. When I met her in 2016, she and her husband had been dating another couple for two years. She was sleeping with the other man. Her husband was sleeping with that guy’s wife.
“We’re all on WhatsApp. There’s a lot of coordination. We have date nights where we swap houses,” Locklear told me. The rule when they started was “Don’t fall in love.” “Well, fuck,” she said, “everybody fell in love.” Locklear asserted that the experience had only made her marriage stronger, because she fell in love with her husband all over again by seeing him through another woman’s eyes. Yes, they do have kids, and their kids (six and twelve years old at the time) are in on what’s happening, to the extent they can understand. Locklear does worry about how this unconventional love quadrangle may affect her preteen daughter (the younger child belongs to the other couple), but said she is constantly trying to explain and give her as much attention as possible.
To clarify: There is an important distinction between polyamory and everything else that falls under the nonmonogamy umbrella. For example, you and your partner might be “monogamish” (like Crawford and Messina), meaning the two of you agree you can see other people but there are certain rules. For one couple, the rule might be that it’s fine to get a little handsy if you stay above the belt. Another couple might countenance one-off hookups or casual side relationships with third parties.
Polyamory is different, in that it involves deep emotional connections, as in Locklear’s situation, rather than simply sex with multiple partners. Adherents believe that love is infinite and that you can feel love for multiple people at the same time; they call it “committed nonmonogamy.” For these reasons, most polyamorists don’t like being compared to 1970s swingers. Advocates describe what they are doing as a brave experiment in human connection. But what happens when the workplace becomes the lab they’re experimenting in?
Though the tech community didn’t invent polyamory, it has certainly adopted it. There’s reportedly even a poly meet-up group at Google. But Susan Fowler’s case is just one example of how the “we’re so cool about sex” culture can create confusion that can bleed into the workplace and foster an uncomfortable power dynamic.
Chris Messina was still working at Uber when Fowler’s blog post hit. “After it happened, I had people ask me about it and I’m like, ‘Whoa, whoa, I’m not condoning the rest of this stuff because I’ve chosen this lifestyle,’” Messina told me. “I see a lot of people looking for excuses for bad behavior—Oh, I can fuck whoever I want whenever I want. No, it’s not okay to do this at work; all the same rules apply. What I’m concerned about is the whole trend around nonmonogamy becomes another justification for not being responsible for yourself and that’s not the point. It’s not a get-out-of-jail-free card. And it creates an environment where, specifically as a woman, you can’t get a break.”
Elisabeth Sheff says the rise of polyamory and other forms of nonmonogamy can have especially dangerous professional consequences for women if their workplace is already dominated by men. “You can’t assume that people will understand that you’re off the market because you’re married” or in a relationship, she says. “Navigating that, being on the market, even though you’re married, can be exhausting, especially for women, who don’t have as much power in the workplace. Now it takes more effort to patrol that boundary. Being on the market never stops.”
There is often a social cost to refusing the endless offers or expressing more traditional views that sexual relationships should be monogamous. “It comes across as parochial and prudish in certain settings,” says Sheff.
The Uber example, for Sheff, represents how this evolution in various types of relationships can lend cover for a new type of sexual harassment. “That’s not polyamory; that’s fucked up,” she told me when we discussed Fowler’s story. “It’s just inappropriate to put people in that position in the workplace. You may think you’re Steve Jobs, but really you’re Roger Ailes or Bill O’Reilly with a Bernie Sanders tattoo.”
Even a woman who is nonmonogamous herself could have problems. “If a woman is known to be polyamorous, then there is this assumption, like, of course she’ll date,” Sheff says. “And if she won’t engage, then she’s a frigid bitch. Women can be at a double disadvantage around this because they still get the sideways looks from other women and from men who think, ‘Well, you’re slutty—why don’t you fuck me?’” One female tech worker who is open-minded told me that her go-to excuse to gently fend off unwanted advances from male colleagues is to tell them she prefers to date women, which is only half true.
Finally, even when all parties consent to some sort of open arrangement, Sheff says, men are more frequently the instigators. “If they are an established couple and one of them says, ‘Let’s become polyamorous,’ very frequently it’s the man. Definitely that’s a dynamic where the man is like, ‘Oh, come on, honey, let’s do this,’” she says. “But sometimes it doesn’t work out quite the way the man expected. Once couples finally start, it’s often easier for the woman to get dates.” That appears to have been the situation of the manager who harassed Fowler.
Sheff is no prude. She believes that the modern form of polyamory in fact gives women more power, and that some women are the instigators in their relationships. “Every traditional society that we know of, wealthy men get as many women as they want. I’m talking China, France, Mongolia, Peru, Canada, everywhere; if you’re a rich guy in 300 B.C. or 2075, you get multiple women. The huge difference now is that women can also have multiple partners. Not all polyamorous relationships are empowering for women, but they are certainly not all exploitative.”
Finding love and keeping love has puzzled humans through the ages, and one might be a little impressed by the bravery and innovation that this generation of tech workers brings to the challenge. But there is so little separation in tech offices between social life and work life and the power dynamics at play that the romantic confusion created by polyamory and nonmonogamy is seeping into the office, increasing tension and opportunities for misunderstandings.
San Francisco has long been a place of sexual norm breaking. It was a club in the city’s North Beach district that is credited in the 1960s with pioneering topless dancing. That style of entertainment, now with the added titillation of private lap dances, seems somewhat old-fashioned. Still, when I heard there was a downtown strip club that was often packed midday with young men from the tech industry, I threw on a pair of sunglasses and decided to make a visit myself.
My trip to the Gold Club on San Francisco’s Howard Street began at 11:45 a.m. on a Friday. The place is already hopping, and by noon there’s not a seat left in the joint and the buffet line wraps around the perimeter of the room. One reason is that this may well be the cheapest lunch in San Francisco. Just pay the $5 cover charge and the rest is free—all-you-can-eat mountains of meaty fried chicken, thick juicy ribs, chicken taquitos, and a generous dessert tray. The other reason the Gold Club is packed: unlimited topless entertainment.
I take a seat at a table near the back with a female colleague I have coerced into joining me on this awkward reporting excursion, feeling more than a little naive and dumbstruck. The Gold Club is the lone strip joint in the tech-heavy SoMa district, just a block from the Moscone Center, which hosts the biggest technology conferences in the world (Apple’s Worldwide Developers Conference, Salesforce’s Dreamforce, and Oracle OpenWorld). Yelp is just blocks away, as is LinkedIn’s brand-new twenty-six-story skyscraper.
One step into the Gold Club, and you feel as if you’ve been transported to a Las Vegas nightclub, LED lights and all. But this isn’t your usual late-night casino crowd. Construction workers on their lunch breaks sit next to men in suits and tech engineers in hoodies and T-shirts. In some of these groups, a woman or two has tagged along. At the center of it all, a half-naked dancer shimmies up and down a fifteen-foot pole on the main stage.
Around noon, the hostesses start weaving through the tables, catching the eyes of customers who might want something more intimate than the fried chicken. The Gold Club appears to be staffed so there’s a woman for everyone—black, blond, Asian, Latina, tall and short, big- and small-bosomed, tattooed and au naturel.
When a dancer wearing a gleaming-white bra and underwear approaches our table, I introduce myself and confess that I am there to do some reporting. She introduces herself with her stage name, Zorah Rose, and tells me she is a teacher at a public middle school in Berkeley, doing summer day shifts at the club to help pay bills. She says she has met patrons from all of the brand-name tech companies nearby, specifically mentioning Uber, Dropbox, Twitter, and Airbnb. “Salesforce is big here,” she adds. “Yelp employees call this place Conference Room G.”
I ask Rose what exactly is on the menu, besides the dancing and buffet. She tells me that most of the place clears out after lunch, so “you know that the people who are still here want something more.” Besides lunch, nothing’s cheap at the Gold Club. (It costs $10 just to withdraw money from the on-premise ATM.) A lap dance costs $20, $60, or $100, depending on how long it runs and how naked the dancer gets. Or you can just go all out and book thirty minutes in a back room for $375.
“Every girl decides how far they want to go back there,” one dancer told me. “I’m sure there’s all kinds of things going on.” Another dancer confirmed that sex is available for those with the cash.
Rose says she definitely attracts a particular type of man. “I get all the mid-forties, white, married tech execs,” she explains. Compared with Chicago, where she used to perform for mostly lawyers, doctors, and salesmen, her tech clients in San Francisco are much more interested in having a conversation, in addition to all the other stuff. “Basically, they just want a stripper girlfriend for a few hours,” Rose says. “I call it therapy in a sexy outfit.”
Another dancer, Nikki Darling, agreed to chat with me later by phone. She too estimates that male tech workers are the predominant clientele. “Sometimes a group will come in, and guys are like, ‘Oh yeah, that’s my boss that I’m with.’” Business deals happen here all day long, she says. After all, it’s much easier to close a sale when everyone’s in a really, really good mood.
Darling tells me she has two regulars whom she sees outside the club, including a Google employee who’s single and a venture capitalist who’s married. While some of her tech clientele are nice guys, she has also encountered her share of Silicon Valley jerks. “They’re younger, came into money early, and it makes them act kind of douchey, kind of a bit entitled,” Darling says. “They have money or power and know you want their money, and they use that power dynamic in a not-so-nice way.”
In case it isn’t clear from the description above, going to strip clubs isn’t something just a couple of guys in the office are doing once in a while. In certain companies, it rises to the level of a corporate culture that is, in some cases, approved by the men at the very top, with strip club fees being charged back to the company.
Strip clubs are nothing new to business, and they have been part of hard-charging tech culture since at least Trilogy’s heyday in the 1990s. The CEO, Joe Liemandt, a.k.a. Hundred-Dollar Joe, led young, impressionable employees on pilgrimages to Las Vegas, where gambling and naked women were the main event.
Christa Quarles, now the CEO of OpenTable, was taken to the Gold Club at the end of an interview—a job interview!—with another tech company. “It was more like, ‘Hey, everyone, let’s go out and see if this person is a social fit,’” Quarles remembers. She felt it was clearly part of the interview, a sort of test to see if she could, as she puts it, “hang with the bro culture.”
Despite feeling uncomfortable, Quarles didn’t complain. “I felt like what I needed to be successful was being one of the boys,” she says. Quarles ultimately took herself out of the running for that job and kept looking.
Another female founder told me she once shared office space with a male entrepreneur who met friends for the Gold Club buffet weekly. It became such a normal part of his routine that he took new employees to the club for their orientation lunch, including men and women.
What employees do on their own time is, of course, their business. But, without a doubt, attending strip clubs with colleagues during the workday is lethal to company culture. Many of the tech workers who engage in this behavior don’t seem to realize it’s problematic. One founder and investor told me he’s been to the Gold Club at least five times with his friends who also happen to be his co-founders. When I pointed out that outings like this might have influenced the start-up’s bro-ey culture, he agreed. “It was hard for us to hire women. We didn’t hire women, and we’ve tried to be very cognizant of not fucking that up anymore. I’m not a saint in this story,” the founder admitted.
When I told LinkedIn’s co-founder Reid Hoffman about tech employees’ regular outings to “Conference Room G,” he simply said, “That is not good.” Does it matter that they are regularly visiting strip clubs (and attending sex parties) if it’s happening outside the workplace? I asked. “Yes, of course it does,” he said. “We are the habits that we create . . . You have an extra burden to make sure that’s not screwing with your workplace.”
Visiting strip clubs becomes especially problematic when it becomes a test for who is on the team. If the woman is on a job interview, refusing to go will certainly damage her chances of getting the job. But even for women who are already part of the staff, the strip club invitation is a lose-lose proposition. They can either participate and potentially feel humiliated and awkward in front of their colleagues or decline and miss the group bonding and business conversation that will take place there. Uber engineer Ana Medina says she was issued “an open invite” to accompany her co-workers to the Gold Club, “and I never took it. Other engineers asked me to go to bondage clubs and bars, and it was one of those things that I was like, ‘What is this, an SF thing or a tech Valley thing? Or is this company so fucked up that this is what gets talked about?’”
Of course, sometimes women aren’t invited to begin with. One female founder told me that every time she went to a conference with her team, a group of men would venture off on their own. “At some point in time, everyone would disappear and I was left. You’ll never know how much business happens in those venues,” this founder said.
Like the high-end sex parties, the strip club scene is part of the background noise that women in Silicon Valley have to deal with. It’s a practice that often leaves women in an untenable position. There is no parallel problem for men. Work and private lives are mixed together in Silicon Valley and the new sexual adventurism inevitably informs how male dominated workforces perceive the few women in their midst. As one Bay Area sex therapist told me, “Women are seen as sexual objects, and their objectification is everywhere.”