What Silicon Valley Thinks of Women

By Nina Burleigh – NEWSWEEK
BusinessSilicon ValleyTech Industry

On a spring afternoon last year at an outdoor café in San Francisco, two denizens of the tech community sketched out their strategy for a startup. Like most 28-year-olds in Silicon Valley, they had smarts and dreams. One was a passionate, fast-talking New Yorker, the other a shy computer whiz from Syracuse, New York, and together they formed the classic hacker-hustler team behind many of the valley’s Next Big Things.

They had been emailing each other about the idea for months, with growing conviction of its awesome potential. It addressed a well-known problem, one that afflicts the tech industry but also banking, media, advertising and film. Corporations needed it. Individuals would love it. It might even be disruptive, as they say. That afternoon, over lunch in the California sun, they committed to an ambitious business plan. That summer, they would keep their day jobs at media and advertising companies, but devote many off-hours and weekends to the startup. The savvy talker, who had worked in communications at Citigroup and Thomson Reuters, joined professional clubs, sought out older advisers, arranged meetings and worked at creating buzz that just might pique investors.
The programmer toiled at the computer, coaxing an algorithm, often alone.

Four months later, the hustler won the project’s first investor, a woman who works at one the world’s biggest hedge funds. It was a small sum, but the entrepreneurs quit their jobs the next day, setting up camp in a donated corner of another startup’s loft office above San Francisco’s Union Square. The new digs mercifully provided free food.

In the ensuing months, the pair eschewed new clothes, walked instead of Ubered and assembled a small, mostly unpaid staff. They found pro bono lawyers with startup expertise, signed contracts, designed and revised their PowerPoint pitch a dozen times and met with more than 50 potential investors. The programmer tested the algorithm. They had 1,500 clients wait-listed for a beta launch. They attracted interest at five large technology companies, including Twitter. They told investors their project was the next Pinterest—the way screenwriters tell movie moguls their scripts are the next Titanic.

Nine months after that day at the café, they launched their startup last month.

In a community like Silicon Valley, where six- and seven-figure investments are routinely tossed at ideas that sometimes succeed but more often flash-bang and fizzle out like meteors, they were getting only paltry sums—about $400,000 shy of the $525,000 they were hoping for in “pre-seed,” early investment money.

There is, though, one thing these two founders are missing, and it is almost the sine qua non of the fabled Silicon Valley startup. They don’t have penises.

Dana Settle is pictured age 27 at a meeting at the Mayfield Fund in 2000. Settle worked at The Mayfield Fund, among the oldest VC firms in tech, before moving on to co-found a VC firm named Greycroft Partners. Bob Sacha/Corbis

Gang-Bang Interviews

The legendary names of Silicon Valley are well known, and for the most part, the men behind the names look like this: geeky, in jeans and T-shirt, maybe with a hoodie, maybe shaving, maybe a college dropout, coding since early pubescence in the upper-middle-class parental basement. They walk into a venture capital firm on Sand Hill Road in Menlo Park or in San Francisco’s SoMa district, and they walk out with a million dollars. A few years later, if all goes well, an IPO makes a lot of people richer.

Computer programmer Lauren Mosenthal and her partner, Eileen Carey, came to California attracted by that kind of possibility. The only problem with their dream is that Silicon Valley has never produced a female Gates, Zuckerberg or Kalanick. There are a few high-profile female entrepreneurs in the Bay Area, but despite the very visible success of corporate titans Meg Whitman, Sheryl Sandberg and Marissa Mayer, who signed up with companies after they took off—their numbers are relatively minuscule.

Despite that discouraging fact, the two women spent their 20s deep inside the valley’s bro community—a culture that has been described as savagely misogynistic. In inverse ratio to the forward-looking technology the community produces, it is stunningly backward when it comes to gender relations. Google “Silicon Valley” and “frat boy culture” and you’ll find dozens of pages of articles and links to mainstream news articles, blogs, screeds, letters, videos and tweets about threats of violence, sexist jokes and casual misogyny, plus reports of gender-based hiring and firing, major-league sexual harassment lawsuits and a financing system that rewards young men and shortchanges women.

There was the young executive of a company valued at $250 million who got up in front of an audience at a conference billed as diverse and joked about “gang-bang interviews” and how he got his start by sending elusive CEOs whose attention he needed “bikini shots” from a “nudie calendar” he’d made of college women. It’s the sort of place where one of the valley’s “most-eligible bachelors,” Gurbaksh Chahal—an entrepreneur with companies valued at hundreds of millions of dollars—is shown on a home security video beating his girlfriend for half an hour. (He received no jail time, pleaded guilty to a misdemeanor and received 25 hours of community service and three years’ probation.) It’s a community in which the porn-inspired, “drading” college tweets of Evan Spiegel, the CEO of Snapchat, go public; where a CEO’s history of domestic violence has no repercussions but female executives get fired for tweeting about sexist jokes they overhear. It’s a place where companies routinely staff conference booths with scantily clad “code-babes” and where women are so routinely sexually harassed at conferences that codes of conduct have become de rigueur—and the subject of endless misogynistic jokes on Twitter.

It is still the kind of place where investors can tweak women who ask them for financing with barbs like “I don’t like the way women think. They haven’t mastered linear thinking.” This was how one investor turned down Kathryn Tucker’s pitch for RedRover, an app that helps parents find kid-friendly things to do, which has since launched in New York, San Francisco and Atlanta.

Three high-profile sexual harassment lawsuits have been filed against Tinder, the virtual town square of hookup culture, and two of the biggest venture capital firms—Kleiner Perkins Caufield & Byers and CMEA Capital. The complaints include a senior CMEA partner harassing a series of executive assistants like a character in Mad Men, replete with sexual nicknames, trapping them in his office and frequently referring to porn and pubic hair. At Kleiner Perkins, former partner Ellen Pao says partners countenanced harassment and retaliation from a fellow partner, and excluded women from client dinner parties because they “kill the buzz.” At Tinder, a male co-founder (and ex-boyfriend) sent abusive texts and yanked co-founder Whitney Wolfe’s title because, she alleged, he told her having a woman on a board “makes the company seem like a joke.” Tinder and CMEA settled under confidential terms within months. That CMEA partner is no longer with the firm, and Tinder temporarily suspended the executive involved. The suit filed by Ellen Pao—who is now at Reddit—is headed to trial this spring. Kleiner Perkins has denied the allegations and stated that Pao “twisted facts and events in an attempt to create legal claims where none exist.”

It wouldn’t be an exaggeration to say that a front line, if not the trench of the global gender war, is in Silicon Valley. In that sense, Silicon Valley culture echoes the Wolf of Wall Street culture in the ’80s and ’90s. But while Wall Street today seems tamer—thanks to lawsuits and diversity consultants in every corner—in Silicon Valley the misogyny continues unabated. A combination of that very traditional Wall Street wolf-ism among Northern California’s venture capital boys’ club and the socially stunted boy-men that the money men like to finance has created a particularly toxic atmosphere for women in Silicon Valley.

This matters for tens of thousands of reasons, but on the broadest level, since digital technology is our era’s Industrial Revolution, fortunes being made now and business models and corporate cultures forming today will be with us for a century to come—and women are for the most part sidelined. Zuckerberg, Gates, Thiel, Musk—these are our Carnegies and Morgans and Rockefellers, whose names will be on museum wings and university halls 100 years from now. And there’s not a female among them.

Venture capitalists often blame the dearth of women graduating in computing and math and engineering, but that is only part of it. As Jodi Kantor wrote in a New York Times article tracing the fates of the Stanford class of 1994, many women with such degrees simply bailed out, while their male counterparts went on to make fortunes as the Internet exploded.

A recent report on women entrepreneurs by the Kauffman Foundation identified the chief challenges to female entrepreneurship. Researchers interviewed 350 female entrepreneurs, and most cited “lack of available advisers” at the top of their list. Female professional attrition is only one reason for the scarcity of mentors for younger women. Another is that women who stay in the game beyond their late 30s may be less subject to sexual harassment than their younger counterparts, but they are sidelined by virulent ageism in the industry that especially—but not solely—afflicts women.

Younger women, setting out on careers in tech, are furious. One group wrote a scathing “Open Letter to Tech” last year complaining about regular “rape-y emails” and professional exclusion.

Shanley Kane is a young tech industry observer and founder of Model View Culture, an acid-penned, widely read website on which she routinely exposes and excoriates the white brogrammer establishment. In an interview with MIT Technology Review in December, she said venture capitalists talk about the need to get 10-year-old girls into science in order to bring up the numbers of women they will fund, but don’t fund the ones already in the industry. “We are not getting hired, and we are not getting promoted, and we are being systematically driven out of the industry,” she said.

Asked what women should do, Kane wasn’t encouraging: “I don’t have a lot of advice. There’s not a whole lot you can do to keep your career from being crushed by misogyny.”

From left, Lauren Mosenthal and Eileen Carey are co-founders of Glassbreakers. Ashley Jones

Kicking Glass

Every successful startup pitch begins with a problem, followed by a solution and an estimation of how many people will pay for it. Carey and Mosenthal are well versed in the problems women in tech face, and that’s how they came up with the idea for their startup, which they called Glassbreakers.

Glassbreakers is a peer-mentoring platform for companies that want to retain and promote women, and it’s also for individuals because it matches women in the same profession with other women at relatively similar levels so they can share tips, contacts and skills. Based on a “software as a service” business model, it relies on an algorithm Mosenthal continues to refine to produce a product that’s a bit like a dating site, matching people by location, career goals, background and needed skills. “Glassbreakers is a $100 million-a-year opportunity for investors, given how many organizations lack the resources to build mentorship programs but are seeking a solution,” Carey says.

But there is “added value,” as she puts it in her pitch to investors: community-building for working women. “A more connected female workforce is a stronger one,” she says.

Founders Jaclyn Baumgarten, left, and Ari Horie discuss a project during a meeting with entrepreneurs at the Women’s Startup Lab in Menlo Park, Calif., May 27, 2014. Patrick Tehan/Bay Area News Group/MCT/Sipa USA
That’s an added value close to Carey’s heart. She hails from a family of East Coast feminists, and her aunt, Noreen Connell, was a member of the New York Radical Feminists, a National Organization for Women leader and Bella Abzug comrade-in-arms who co-wrote a 1974 sourcebook for rape victims. Carey is named after her mother: “I’m Eileen Junior.” She admits she has only rarely experienced sexual harassment or even sexist behavior. “Women our age expect feminism,” she says, sitting in a sunny, donated corner room in the loft offices of Prism Skylabs, a retail analytics company. “We expect to be treated equally. That shit would never fly around me.”

But she knows bias and harassment are endemic in her profession. When she hears such stories, she encourages the women to report the men, but she understands why they don’t. She has no such qualms herself. “I have seen people sexually harass people, and I have reported it to HR or their bosses,” she says.

Glassbreakers’s peer-mentorship model is different from the traditional mentorship model, Carey says. It aims to mitigate the effect of female professional attrition on younger generations of women coming up. “Traditional mentorship, established in male-dominated industry, is between very senior and very junior people. But the problem for women in the workforce is that there are many more mentees than mentors. Also, the tech industry is changing so fast that women even five or 10 years older may have very little of practical use to share with younger workers.”

Around 1,500 women signed up for last month’s launch, which was confined to the Bay Area. Customers who sign up provide information about their skills and professional goals, and thanks to Mosenthal’s algorithm, they will find three names in their inbox and the user decides whether to make the connection. The two plan to eventually tailor Glassbreakers platforms for women in other industries.

After their first investment, the women raised $100,000, including their combined personal life savings of $15,000 each. Carey says she met with around 50 potential investors, and if the launch goes well, and she can show both significant interest and that the product works without glitches, this month she will be heading out on her first “seed round”—startup lingo for pitch meetings with venture capitalists aimed at raising enough money—she wants $1.5 million—to keep going for 18 months.

The road to launch wasn’t easy. Investors did not pony up the pre-seed financing goal. The company made it to the interview stage of the coveted Y-Combinator tech incubator but no further. Carey says those setbacks were balanced out by promising signs, including the ardent support of older influential women, like the woman who ponied up their first investment.

She also picked up some male investment interest, including funding from Ben Parr, founder of the DominateFund and formerly of Mashable, who invested $20,000 in Glassbreakers just before the launch. “I’ve been talking to women about this problem for years,” Parr says. “A lot of men would write this off. If they build the community, the possibilities and opportunities are enormous—especially for Glassbreakers within workplaces.
Conference attendees at TechCrunch Disrupt at Pier 48, Sept. 8, 2014 in San Francisco. Steve Jennings/Getty

Asking for It

“We are confident women!” It’s a mantra Carey repeats, half-earnestly, half-smiling, as she prepares for a pitch meeting. CEO Carey does those alone; Chief Technology Officer Mosenthal will come only when and if the investors want to talk technology. Carey says that having two of them in the room when she’s asking for money “breaks the energy.”

But asking for money didn’t come naturally—and that’s part of the problem for women in tech. It’s not all sexism but also a culture in which women don’t easily brag or bring the same swagger to fund-raising pitches that the boys do. She and Mosenthal bootstrapped (startup talk for self-financing) for months. Even after she had her rap down for the pitch, she had to be coaxed across the line. In August, she met at a Starbucks with a woman affiliated with a major hedge fund. Over the course of an hour, Carey explained the Glassbreakers platform. The woman, who invested her own money and prefers to remain anonymous (she doesn’t want her company involved), clearly “got” the problem. At some point in their conversation, the woman gently advised Carey that it was important to come out and ask for money.

“At the end of the meeting, she asked straight out, ‘Are you going to ask me to invest in your company?’” Carey says. “And I said yes.”

That investor ponied up less than $10,000 but says she likes Glassbreakers as a business prospect because of various corporate initiatives, such as Intel’s recently announced $300 million, five-year commitment to women’s leadership and diversity. “That’s a trend that will be very favorable for a technology like Glassbreakers,” the investor says.

The effect of that investment on Carey and Mosenthal was exponentially greater than the relatively small dollar figure. “Next day,” Carey says, “we quit our jobs.”

Carey’s unease about asking for money doesn’t surprise Vivek Wadhwa, a Silicon Valley investor, diversity coach and author of Innovating Women. Wadhwa says shaky self-confidence is one of the chief things holding women back. It’s not just about the money, though. Wadhwa says women not only are reluctant to overstate their accomplishments and goals; they habitually understate them. “Often I have to say to them, Why are you underselling?” he says. “When I coach women, I tell them how wonderful they are. Women won’t make the ridiculous projections about their companies that the guys will. They won’t say the really stupid thing the nerds do. They are a lot more realistic and practical and humble.”

Stanford engineering graduate student Serena Yeung, second from left, meets up with other male engineering students Arturo Escaip, left, Subodh Iyengar, right, and Rathul Sheth, second from right, on the Stanford University campus in Stanford, Calif., May 30, 2012. Paul Sakuma/AP

Gender-gating

No amount of confidence changes the fact that the valley’s big venture capitalists are almost entirely male. The top five don’t have any female senior partners, and VC partners are 96 percent male. Twenty years ago, the partners were 97 percent male.

A new generation of millennials starting their firms have hardly changed the system. Some of the wealthiest men in the New Billionaires club are Peter Thiel (who financed Zuckerberg) and David Sacks—two guys who spent their formative years at Stanford in the 1990s writing anti-feminist screeds for their school paper. According to Kantor in The New York Times, “In the pages of [Stanford’s] The Review, they defined feminism in negative terms—alarmist, accusatory toward men, blind to inherent biological differences. Feminists ‘see phallocentrism in everything longer than it is wide,’ Mr. Sacks wrote. ‘If you’re male and heterosexual at Stanford, you have sex and then you get screwed.’”

Speaking to the Times, Sacks regretted his collegiate anti-gay screeds, but didn’t seem too concerned about the juvenilia directed at women, nor the status of his female co-eds, the majority of whom dropped out of the business.

VCs are not funding women. According to a study by Babson College, only 2.7 percent of the 6,517 companies that received venture funding from 2011 to 2013 had women CEOs. Meanwhile, the Kauffman report found that female-run startups produce a 31 percent higher return on investment than startups run by men.
One problem with the male-dominated system is that top partners have almost never been exposed to women as professional peers. Their interaction with women is limited to their wives and daughters, and maybe executive assistants.

Male VCs who don’t have female professional peers are especially difficult to pitch on products that serve a female market. “Dozens of times, women have come and told me, I pitched to a firm and what do I hear over and over, ‘Oh, I will go home and ask my wife about it,’” says Trish Costello, an entrepreneur and founder of Portfolia, a venture capital investment platform designed for women. She is also CEO emeritus and co-founder of the Palo Alto–based Kauffman Fellows, a global training institute for venture capitalists.

A prominent venture capital investor from one of California’s top firms, who asked not to be identified because he didn’t want his firm “singled out,” called the absence of female partners “embarrassing” but said it’s directly related to the smaller percentages of women graduating from the engineering schools. “There is no question that diversity of opinion adds to the acumen of the group,” he said. “One of the most passionate business reasons we have to expand the investment to include a handful of women is that they are often not represented in the partnership dynamic around the table on Monday when we are discussing investment ideas.”

But the investor insisted that potential, not gender, was the key to which ideas, of the 10,000 that get pitched to his firm annually, end up being among the 12 that get financed. He added that of those pitches, 20 percent come from female entrepreneurs—which he said tracks with the percentage of women in engineering programs. The investor sits on the boards of two women-run firms that his company financed, and both female CEOs find the focus on their gender “patronizing.”

This is such a touchy subject for the all-male partnerships that few investors want to discuss it—on the record or not. A spokeswoman at Andreessen Horowitz declined to comment, and Peter Thiel’s firm, the Founders Fund, did not respond to messages.

To be fair, there are many reasons Glassbreakers might not appeal to a Founders Fund or Andreessen Horowitz, or any of the dozens of other all-male VC partnerships on Sand Hill Road in Menlo Park, reasons that have nothing to do with sexist bias. It’s not likely to be a Facebook, or even a Houzz, the home-remodeling site launched by an Israeli husband and wife, financed by Sequoia and now valued at $2.3 billion. Glassbreakers is by definition “gender-gated,” thereby excluding 50 percent of potential users. It also presumes that many women do feel the need for female mentorship, when in fact there is quite possibly a significant cohort of working women who think they are getting along just fine without another woman’s advice.

That said, if the Glassbreakers launch shows a market for the product, it will almost certainly have a longer life than Red Swoosh, a now-forgotten Travis Kalanick file-sharing enterprise that venture capitalists threw millions at, and which, when it sold for $19 million, enabled the young founder to buy a San Francisco mansion and Uber.
Should the Glassbreakers team fail in the next 18 months, odds are much worse for them than for men that they will not get more funding. Wadhwa often talks about the importance of “pattern recognition” among VCs. The male bankers simply have an idea of what a successful startup founder looks like, and young women like Carey and Mosenthal simply don’t fit.

“Women don’t look like winners. So they can’t fail, while boys in the club can,” Wadhwa says.

To avoid this, Carey has vetted the venture capitalist firms she will approach, seeking those that have funded other female startups, and making sure that they have some women in senior, decision-making roles. “Of the VCs we have had the highest engagement with, three are women-led firms,” Carey says.

The financing gap between male and female entrepreneurs is massive. VCs typically fund women at the lowest levels—$100,000. The Kauffman study found the majority (nearly 80 percent) of female entrepreneurs didn’t get venture capital but used personal savings as their top funding source. Carey found a network of women, some of whom are or have been venture capitalists or who have started companies. Among their bits of wisdom was one that is antithetical to the swaggering male startup CEO who is sure he’s going to be the Next Zuck. “Talking to these women, we learned you have to ask,” Carey says. “Don’t pretend you know something. If you are honest about what you don’t know, people are more responsive.”

But the advice that bothers her most, Carey says, has to do with how to deal with her own gender. “We are very fortunate and haven’t faced discrimination in our lives,” Carey said of herself and Mosenthal. “I’ve never been told I would not be able to do something or that it would be harder to do because I was a woman. So it’s been strange going through this experience and being told that because we are women it will be harder for us to fund-raise. The hardest part has been hearing that and digesting it and accepting that our gender would be a barrier for entry. I never thought it would be this real.”

Sheryl Sandberg visits the Facebook France offices, April 14, 2014. Elodie Gregoire/REA/Redux

“This Really Happened”

Heading out on her first financing round, Carey is well aware of the worst things that can happen to a young woman seeking money for a startup. The stories are rampant—in fact, every woman entrepreneur who’s been around Silicon Valley has one. For brevity’s sake, we present one from entrepreneur and venture capitalist Heidi Roizen.

Early in her career, Roizen was working “on a company-defining deal”—involving, potentially, millions of dollars—with a major PC manufacturer. “The PC manufacturer’s senior vice president who had been instrumental in crafting the deal suggested he and I sign over dinner in San Francisco to celebrate,” Roizen has written. “When I arrived at the restaurant, I found it a bit awkward to be seated at a table for four yet to be in two seats right next to each other, but it was a French restaurant and that seemed to be the style, so down I sat. Wine was brought and toasts were made to our great future together. About halfway through the dinner, he told me he had also brought me a present, but it was under the table, and would I please give him my hand so he could give it to me. I gave him my hand, and he placed it in his unzipped pants.

“Yes,” she said. “This really happened.”

Every Silicon Valley entrepreneur who spoke with Newsweek has a story somewhat like this—varying only in degree of brazenness. One young woman had worked for a year on a startup with an older male financial mentor. When she was ready to head out for a round of funding, he took her to dinner—a meeting at which she expected to be introduced to VCs or told which ones he’d arranged for her to meet with. Instead, over wine, he confessed that he was having a midlife crisis and that he was in love with her. No finances would be forthcoming.

Roizen stayed in the business and is now one of the industry’s legendary female entrepreneurs. Wadhwa says women must approach male VCs with caution and awareness: “Women don’t get it. The young women don’t seem to understand the reason why they get their calls returned so easily and get small amounts of funding is they are dealing with hungry men. These are disgusting perverts. Some of them used to be my friends—sexist jerks. And I know how they speak behind the scenes.”

To head this off, Carey recently dyed her blond hair mousy brown and dresses down, not up. Now she meets with investors only after researching them or getting references from other women. “We are vetting them left, right and center. We don’t take meetings over drinks. I do know a guy who raised a million dollars and got blackout drunk every night with the VC. That’s not how we work.”

Carey says the slightest sexist overtures dent her confidence. “When an investor kisses me on the cheek on the way out, I feel like shit for weeks afterward.”

Google employees eat lunch in a cafeteria adorned by artwork created by Google employees, in Mountain View, Calif. Jan. 6, 2006. Eros Hoagland/Redux

Viagra but No Abortions

The Glassbreakers women are launching a product for women, designed to solve a problem women understand better than men, in an economic sector that has traditionally produced products shaped by the minds of young men for young men. It’s inarguable that white, upper-middle-class young men have applied the new technologies to make things that reflect their desires and culture and foisted them on the world. Women who complain about sexist video games get death threats from legions of boyfans conditioned by formative years on the Xbox controller to believe it’s their right to rescue—or maybe assault—wasp-waisted half-naked damsels in distress. And the anonymity of the Internet has proved relatively more menacing to women.

None of these ill effects are deliberate, but they are built into designs and products created almost solely by one gender. As recently as 2011, for example, Apple made a Siri who could find prostitutes and Viagra but not abortion providers.

Reviewing the movie The Social Network, the writer Zadie Smith wrote that everything about Facebook is “reduced to the size of its founder. Poking, because that’s what shy boys do to girls they are scared to talk to.” Ultimately, she wrote, The Social Network wasn’t “a cruel portrait of any particular real-world person called ‘Mark Zuckerberg.’ It’s a cruel portrait of us: 500 million sentient people entrapped in the recent careless thoughts of a Harvard sophomore.”

Frustrated, women in Silicon Valley seem to be segregating themselves in women-only venture funds or starting gender-gated funds.

Costello says that the sexual harassment lawsuits and the public talk about endless ugly events is a sign that things are changing. “We are in a major time of shift. There is no other time when women have been better educated, earning a majority of undergraduate and graduate degrees and serving in equal numbers in nearly all professions. The control of personal wealth is about equal, as baby boomer men are dying earlier and women are inheriting money from their parents and husbands and have their own assets from working. If we can access 2 percent of that money controlled by women, we don’t need to be begging on Sand Hill Road.”

Corrections: This article originally misspelled the last name of Ben Parr. This article has also been updatedto reflect that three high-profile sexual harassment suits against Tinder, Kleiner Perkins Caufield & Byers and CMEA Capital were not all filed in 2014. 

Clarification: An earlier version of this article originally stated that Dana Settle works at the Mayfield Fund. Settle worked at the Mayfield Fund at one point before moving on to co-found a competing VC firm named Greycroft Partners.