Brotopia: Breaking Up the Boys' Club of Silicon Valley

by Emily Chang

Katrina Lake, the CEO of Stitch Fix, heard Sacca extol his hot tub test at a conference. “As a woman, I’m sitting there thinking, ‘I don’t want to go all the way up to Tahoe and sit with this guy in a hot tub.’ At that point, I’m like 100 percent not going to get invested in by Chris Sacca,” Lake concluded. “Was he discriminating against me? No. But at the same time, I feel I don’t have all the options available to me because of the way deals are done in Silicon Valley. How many women want to get in a bikini and drink beers while pitching a business?”

“Absolutely, wealth can change people,” one former Google executive told me. “It disconnects you from average people. It’s a big, big problem. You assume your experiences are everyone’s experiences, and with wealth that becomes dangerous. Moral exceptionalism is disgusting, and Silicon Valley has tons of it, and it stems from a lack of empathy. You assume the people who don’t see the world as you do are uneducated or stupid.”

When I started writing this book, several people suggested Silicon Valley couldn’t possibly harbor more gender inequity than Wall Street. When it comes to the numbers, those people are simply wrong. Women account for almost half of employees at the top U.S. banks (though banks still have work to do when it comes to promoting women into leadership positions). One Goldman Sachs banker turned entrepreneur, Nicole Farb, told me she felt far more isolated as a woman trying to raise funds in Silicon Valley than she ever did in finance. “I think the investment banks are more forward thinking than the venture funds, and that’s sad,” Farb told me.

Cosmopolitan even interviewed Grace Hopper, who compared programming to planning a dinner, something she said women are expert at because of their patience and attention to detail. “Women are ‘naturals’ at computer programming,” Hopper declared matter-of-factly. Cosmo backed her up, declaring this “a whole new kind of work for women . . . Telling the miracle machines what to do and how to do it . . . and if it doesn’t sound like woman’s work—well, it just is.”

In fact, new technology was often sold as a way to replace women in the office. One ad for Optical Scanning Corporation read, “What has sixteen legs, eight waggly tongues and costs you at least $40,000 a year?” The pictures depicted the answer with tight shots of the legs and mouths of eight female office workers.

If you select for an antisocial nerd stereotype, you will hire more men and fewer women; that’s what the research tells us. The prevalence of antisocial personality disorder, for instance, favors men by a three-to-one ratio.

Emily Grijalva of SUNY at Buffalo found that men consistently score higher than women when it comes to narcissistic traits such as exhibitionism, feelings of entitlement, and the willingness to employ unethical or exploitative behavior to get ahead.

“Brainteasers are a complete waste of time,” Google’s longtime former head of HR Laszlo Bock admitted to the New York Times in 2013. “They don’t predict anything.”

Men are far likelier than women to take risks like these and to feel comfortable doing so. Geoff Trickey, managing director of Psychological Consultancy Limited, a group of business psychologists, studied risk-taking behavior in over seventy-five hundred people and found that risk takers who are both impulsive and fearless were twice as likely to be men as women. On the flip side, female risk takers were roughly twice as likely to be more wary and judicious than men.

An extensive study by the Peterson Institute for International Economics, a nonprofit that studies international economic policy, analyzed nearly twenty-two thousand publicly traded companies across various industries in ninety-one countries. The study found that companies whose leadership was at least 30 percent female were 6 percent more profitable.

One day in 1998, Thiel was guest lecturing about currency trading at Stanford when a young Ukrainian engineer named Max Levchin sneaked in to, as he told me, “sleep and get some air-conditioning.” Instead, he wound up listening. At the end of class, Levchin introduced himself to Thiel and mentioned that he wanted to start a company. He had already started four that had failed, but he wasn’t about to give up. The next day, the two men had breakfast and hatched the idea for PayPal over a Hobee’s “Red, White, and Blue” smoothie. Suddenly a former securities lawyer with no technical background was the unlikely co-founder of what would become a billion-dollar start-up. And the group that would become the PayPal Mafia began to form.

Reflecting on her time at PayPal, Manning told me, “The problem was a cultural one, not necessarily a lack of women, but if there were more women, the culture might have been better. There was a certain overconfidence among the engineers. I wanted a little more process that could have protected us from mistakes, something that I think women can be more sympathetic to. I do think there can be a sort of macho all-male environment of ‘We don’t make mistakes.’” For example, Manning had to fight to get the team to use a bug-tracking system (and one engineer programmed it to play “The Hamster Dance Song” whenever it loaded). The team, conversely, felt they could keep track of whatever they needed to in their heads.

To build a healthy culture, Levchin, who has been known to wash his own dishes at Affirm, relies on his two decades of company-building experience. “At PayPal, I would argue all of us were so young and running quickly,” Levchin says, while at Slide he made far too many “poor cultural choices.” “With benefit of hindsight, Affirm is very different,” he says.

In his novel The Rise of the Meritocracy, Young portrayed a dystopian Britain in which status based on birth and lineage was replaced by status based on education and achievement. Young wasn’t advocating for a return to the old system, but he did see grave dangers in the new embrace of meritocracy, eerily predicting that in this new world, status would still be accessible only to a select few: those who had access to elite education.

When you are convinced your organization is a meritocracy, the theory goes, you can often forget to do the hard work of rooting out gender and racial biases.

At one point, a recruiter remembers Page ordering the team to stop hiring male engineers until they had hired twenty female engineers in a row.

Around 2008, Google also established a secret hiring practice to ensure that women engineers did not fall through the cracks. “If a woman failed an interview, a second committee was assigned to review the case,” a former Google executive tells me. It was called the Revisit Committee, and it included women engineers who would take a closer look at candidates on the verge of being denied.

The “Elephant in the Valley” study (yes, that’s its real name) found that of the more than two hundred women respondents (most of them having had at least ten years’ experience), the vast majority—90 percent—reported witnessing sexist behavior at industry off sites and conferences.

Tracy Chou once wrote this about the “uncomfortable state of being Asian” in tech: “It’s not as ‘good’ as being White, but it’s certainly ‘better’ than being Black or Latin@, and it’s good enough that we don’t complain about the erasure of our individual identities and work ethic and personal successes, we don’t complain about the bamboo ceiling, we stay quiet on issues of race.”

Investors generally do see women’s businesses differently than their founders do. One VC told me, “I’d love to fund more women, but I just don’t want to fund another e-commerce company!” This comment points to the same issue that some VCs have complained to me about privately: that too many women choose to start companies in sectors where growth is expected to be lower, such as e-commerce and parenting, rather than in areas with huge growth potential, such as artificial intelligence. A lot of low-growth businesses are viable; they just don’t have the kind of enormous upside that excites investors who are successful enough to pick and choose. In 2011, Mashable reporter Jolie O’Dell tweeted, “Women: Stop making startups about fashion, shopping, & babies. . . . You’re embarrassing me.” Her comment triggered the typical social-media uproar, but there is some truth to it.

In a comprehensive survey in 2017, TechCrunch found that 31 percent of start-ups with a female founder focused on e-commerce. Other sectors popular among women were education, health care, and media and entertainment. But the vast majority of venture capital in 2016 went into fintech (meaning financial tech, such as apps that disrupt banking and retirement planning), security, genetics, augmented and virtual reality, and artificial intelligence, in addition to an outsize amount in transportation (dominated by funding of Uber, Lyft, and other ride-hailing services).

“There are a lot of women in the LP community, but all of us would say the same thing,” says Joelle Kayden, founder of Accolade Partners, a limited partnership that invests in a variety of different venture firms including Accel and Andreessen Horowitz (two firms that had no female investment partners as of 2017). “We’d like to see more women [at venture capital firms], but if you stuck a gun to our heads, we’d invest based on returns.” Kayden’s job, after all, is to deliver returns to her own investors.

As for Aileen Lee, she now hosts an annual gathering of powerful women at her home, where the husbands and partners of the guests don suits and pass out the drinks. At the most recent event, Chamath Palihapitiya kindly served me some sparkling water. In case her intentions weren’t already clear, Lee dubbed the event Ladyfest.

Most companies, unfortunately, don’t “step up,” as Sandberg advises; they wait to get pushed. It took a report from the former U.S. attorney general Eric Holder for Uber to move its dinner offering from 8:15 to 7:00 p.m. Holder was tasked with critiquing the company’s culture after Susan Fowler’s accusation of sexual harassment came to light. Holder noted that an earlier dinner would allow a “broader group of employees” to utilize the benefit—including those who “have spouses or families waiting for them at home”—and signal an earlier end to the workday. Uber complied.

Taylor believes the women who worked at Facebook faced an even bigger trade-off: “When someone would go on maternity leave, it was like fifty-fifty whether they would come back.”

Like Stewart Butterfield, CEOs need to make hiring and retaining women an explicit priority. In addition, here is the bare minimum of what we can do at an individual and a systemic level: First of all, people, be nice to each other. Treat one another with respect and dignity, including those of the opposite sex.That should be pretty simple. Don’t enable assholes. Stop making excuses for bad behavior, or ignoring it. CEOs must embrace and champion the need to reach a fair representation of gender within their companies, and develop a comprehensive plan to get there. Be long-term focused, not short-term. It may take three weeks to find a white man for the job, but three months to find a woman. Those three months could save three years of playing catch-up in the future. Invest in not just diversity but inclusion. Even if your company is small, everything counts. And take the time to educate your employees about why this is important. Companies need to appoint more women to their boards. And boards need to hold company leadership to account to get to fifty-fifty in their employee ranks, starting with company executives. Venture capital firms need to hire more women partners, and limited partners should pressure them to do so and, at the very least, ask them what their plans around diversity are. Investors, both men and women, need to start funding more women and diverse teams, period. LPs need to fund more women VCs, who can establish new firms with new cultural norms. Stop fu...