Brotopia

by Emily Chang

  “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.”

  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 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 togethe
r 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.