A few years ago, Heather Marie, the founder and CEO of the e-commerce platform Shoppable, attended a conference that matched entrepreneurs with potential investors. She’d set up a few meetings, and one of them, she says, went like this: When she asked whether or not the investor had seen the background on her company, he replied, “No, I didn’t. Actually, I’ve got to be honest with you — I didn’t look into it at all. I just took the meeting because you’re hot.” Marie ended the meeting quickly. “He was being completely disrespectful, wasting my time and wasting my money,” she says.
Marie’s experience with borderline sexual harassment while raising money for her start-up isn’t especially unique. Over the last couple of months I’ve spoken to over a dozen female company founders and more than half of them told me similar stories. Some of the sexism they experienced was overt — being told, while pregnant, “we’d never invest in a pregnant woman” — some of it less so. In all cases, the comments that these women received when trying to get their companies off the ground contribute to a Silicon Valley’s boys’-club culture that continues to exclude women and treat them like second-class citizens.
And this matters. Venture capitalists are the gatekeepers to Silicon Valley and whoever they choose to fund gets into the kingdom. Certainly, it’s difficult to get funding, period — whether you’re a man or woman. One VC has said that for every ten investments his firm makes, they meet with around 1,200 companies. But that doesn’t explain why so few of the investments they do make go to women: as of last year, only about 3 percent. And in the context of a number that low, routine degradation and discouragement begins to seem like a critically important issue.
The pitching system, though designed to be a meritocracy, is ultimately subjective — a 2016 study found that early-stage investors rely on a combination of “gut feeling” and formal analysis when deciding in whom to invest. When a “gut feeling” leads you to ask someone who’s pitching you out on a date instead of investing in them, that’s a problem. When you’re a woman entrepreneur, it seems, sometimes men can’t decide if you’re pitching your company — or yourself.
“It’s subtle but persistent,” says Carol Barash, the New York–based founder of a writing platform for students applying to college called Story2, of the gender biases in venture capital. “It’s not like someone showed up and touched me. But there were lots of little things.” Barash describes how male VCs often emphasize how much they like her, before rejecting her pitch. “Like: ‘I really like you, but I just don’t see how this business can do the things that you’re saying it will. But I like you.’ It doesn’t freaking matter if you like me!” Barash continues. “We’re not dating! I’m asking you for money! I don’t give a shit if you like me.”
Like Barash, several women I spoke to described male VCs making comments that cross the line from the professional to the personal. Liza Darwin, the co-founder of Clover Letter, a newsletter targeted at teen girls, describes her experience raising money as “pretty harsh.” She and her female co-founder were once told by male VCs that they would take them seriously because they weren’t wearing heels. “We also had one person tell us, ‘Anna Wintour is not the best editor, she just dresses the best, and that’s something you guys need to remember when you walk into a meeting,’” Darwin says.
Many of the women I spoke to pointed to the fact that there are so few of them in the room as being one of the reasons why this behavior continues. According to the 2016 Crunchbase Women in Venture report, only 7 percent of investing partners at the top 100 VC firms are women. Several women, whose companies focus on products or platforms specifically for women, say that they regularly encounter venture capital firms that have no female partners or even associates — and besides the awkwardness of being the only woman in the room, there is the added discomfort that comes when the men say they’re going to ask their wives what they think of the pitch. “There’s something about that that’s so offensive,” says a co-founder of a women’s product company who asked to remain nameless. “An investor’s job is to look at the climate, look at the industry, listen to the pitch, look at numbers, and make a decision. If it was like, ‘Oh hey, my wife happens to be in this industry and I want to throw this by her,’ then fine. But it was always, ‘My wife is a woman, she has a vagina, you have a vagina, let’s see if everything aligns.’ It’s so offensive.”
Addressing these comments is tricky, and women say they’re often accused of being “pushy” if they’re too direct with investors, whereas the same confidence and assertiveness would be considered an asset in a man. Brooke Wentz, who founded a music supervision and licensing company called Rights Workshop, recalls an experience when she disagreed with an investor over their competitive set. He later told her co-founder that he wasn’t going to invest because Wentz was “too defensive, too hard-core.” She explains: “When you’re dealing with people who do not know your line of business and are assessing you by either your tone or your overt strong knowledge about something, you get pushback. On the other hand, if I was a guy, this guy would be literally writing me a check.”
The pitfalls of pitching while female are compounded when the woman in question is pregnant. The woman-focused-products co-founder told me that she hid her pregnancy while fundraising until it was impossible to hide anymore. “Once it was kind of clear, the conversation constantly went back to my pregnancy. It was like, forget about my pregnancy, can you listen to my pitch? Instead, it was, ‘Are you taking time off? I know my wife had a really hard time getting back to work afterwards.’ They’d say things like that, which would make me uneasy. Now I have to go into a pitch and convince you that I can do two things at once. So that was always really frustrating.”
A former health-care start-up CEO, who also asked to remain anonymous, was eight months pregnant during the last round of funding she did before leaving the company. “That was when the true colors of Silicon Valley really came out,” she says. “I was told point-blank they would never invest in a pregnant woman.” The worst experience was four days before she gave birth, when she was asked by an investor how much maternity leave she was taking. She says she was planning on taking one week (this was her second child, she hadn’t taken any for her first). “And the response was, ‘I guess you’re not going to be a very good mother, then.’ I was so taken aback that I didn’t say anything. It was one of those questions where I realized there was no good answer. If I said I was going to take tons of time he would have said I was a terrible business leader.”
Even those interactions, though, are somewhat overt — at least these women have gotten in the room. It’s the sexism that women don’t see that might be even more of a problem — particularly for black women, who make up .2 percent of all venture funding. That’s right: point-two percent. A recent study of more than 60,000 start-ups found that only 88 had black female founders, and of those, only 11 had raised more than $1 million in VC funding. To make the disparity even starker: Black-female-founded start-ups raised an average of $36,000, while the white-male-led start-ups that failed raised an average of $1.3 million.
“To me those instances that are loud aren’t the real problem,” said Atlanta-based Cherae Robinson, who founded the Africa-travel-curation site and app Tastemakers Africa. “The real problem is the stuff we don’t know, the bias that’s there that maybe these investors aren’t seeing themselves.” Robinson describes being a black woman founder as “a double negative.” “As a black person, as a woman, I don’t have the connections to these networks of white males who are writing the checks,” she says.
Access can be incredibly, frustratingly hard to get. “You do a Google search on how to get a VC meeting and it’s a bunch of white male VCs talking about how they don’t answer cold emails,” Robinson says. “If I don’t have that network, that cold email might be my only shot. So how about you tell me how to get you to open the cold email? The access issue is just as much of an issue as the bias itself. Once you get in the room you’re already doing better than most.” She recalls a conversation with a white man in her network, whom she told she was trying to raise $1.2 million. “He said, ‘Oh, that’s easy.’ That’s easy for you, John. It’s not easy for me.”
Stephanie Lampkin, who founded a company called Blendoor, has raised around $150,000 in outside capital — a figure that she says pales in comparison to her white male peers in the same space. She also found that raising money from people of color had not gone as well as she’d hoped. “That was a big revelation — that I’m not going to get support from the people who are most obvious. I do think my biggest check is going to come from an old random white guy somewhere who’s just sick of investing in the same people all the time.”
It’s tempting to look at the women who do stick it out and conclude that they’re somehow stronger for the experience. And certainly, many women I spoke to say they don’t regret trying to raise money for their companies. But there were a few very emphatic exceptions. When I asked one woman what advice she’d give other female founders, she said, “I wouldn’t recommend women go into tech at all. The industry is so toxic. There are thousands of ways you can be technical and not be in the Silicon Valley space.” For some women, the whole sector feels so stacked against them and so saturated in sexism that they just want to have nothing to do with it; even women who say they didn’t regret it joked about having PTSD. Hardly a ringing endorsement of the system.
And all of them have strong opinions about how the system needs to change. One is that there need to be more female investors, period. There also need to be more men taking chances on women, so that the few women who are in venture capital don’t feel like they have to always be the ones to invest in other women.
People on the other side of the table are trying to change that. There are organizations like Pipeline Angels, started by a woman named Natalia Oberti Noguera in 2011, that match up female investors with female entrepreneurs who have started for-profit companies with a social or environmental mission. “The women of color who come to us with a pitch often don’t have a friends or family option,” said Jenn Viane Riese, who started investing with Pipeline a couple of years ago. “They go right from bootstrapping to us. There’s not a ton of options where they feel like there’s a safe environment for them to pitch.”
But even if more women start flooding venture capital, ultimately things probably won’t change until mostly male VCs realize that there’s money in diversity — racial, gender, ethnic, and age. “We’re not going to be successful if we play this gender and race game as a shame game, like, ‘Shame on you for not having women on the board,’” Lampkin said. “It has to be something where we show the benefits of changing the rubrics and changing the game.”
In the meantime, the few female VCs, like Tracy Chadwell of Greenwich-based 1843 Capital, said that male VCs’ lagging understanding of the marketplace has given her firm an opening. As she put it: “The perception-distortion field has left some really amazing female-founded companies that are available for me to invest in.”