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When I talk to women in venture capital, they often tell me, “It’s hard being the only woman.” Female investors are frequently put in positions where they are one of a few women at a firm—and sometimes the only woman.
“It’s shocking to me that it’s so stark,” one VC told me, “but there’s no diversity in venture capital, period.” Another described the industry as feeling a “little bit like high school.” That appears to be changing slowly, as the industry becomes more self-aware—and as women push for change in the industry and usher in a new crop of female-run funds. I talked to female investors* about some of the things they’ve encountered when they’re the only ones in the room.
You may feel singled out in the office . . .
Saira, a VC based in the Midwest, was pregnant but not showing when she joined her firm. She says her pregnancy was something of a litmus test for her, especially since at the time, she was also the only woman on her team. But her experience—and the response to her pregnancy—was positive, though she attributes part of that to location. “My perspective is that most people put family first [here],” she says. “So the good news is, I feel like that makes it an easier environment to succeed as a woman because you’re not expected to make sacrifices like you might be [elsewhere]. In New York, I feel like you’d be gunning against a man who would judge you if you had to leave early to go pick up your sick child from school.”
But at the same time, she says the “greater family orientation” can breed more bias. “I do think that in the Midwest, you see more stay-at-home wives,” she says. “When I compare the best males I’ve worked for or with to the worst males I’ve worked for or with, one thing I’ve noticed is men who have working wives are just better men to work with.” And while she doesn’t think family trade-offs have exactly hurt her career, she feels the weight of being one of the only women. “I became more acutely aware of being a woman in the room once I had children,” she says. “Up until then, I could work as hard. I could do just as much . . . post-children, there are definite disadvantages.”
. . . And out of the office
The feeling of being at a disadvantage follows you out of the workplace, too. “When I was younger I was a little bit oblivious, and I think that helped me out a lot,” Saira says. But earlier in her career, she was on an all-male engineering team—after having studied engineering in a supportive, co-ed environment—and said it was the first time she fully recognized her gender could be an issue. “There was a camping trip that all the guys on my team organized and went on,” she says. “And I was the only one who didn’t get invited. I was shocked . . . It was such a small, subtle thing, but it was the first time I felt it.”
Often, it’s not that women VCs don’t get an invite to events, but that they don’t feel particularly welcome when they do. “A lot of people—and it tends to be men as opposed to women—don’t realize that they’re making other people uncomfortable with what they’re saying or doing,” says Kristin, a Chicago-based VC. Some female VCs opt to skip events that they suspect will be a bro fest, but that can also feel like a missed opportunity. “It becomes a lot harder to avoid, because then you’re also presented with the question of, well, this is where I’m going to meet the people that I want to be meeting,” Kristin says. “If it’s in theory something that you’re uncomfortable with because of the timing, or the situation, then you’re kind of putting yourself at a disadvantage.”
Another VC adds that while things can get blurry—especially when peers in the industry become friends—she has found the venture capital scene in New York far more diverse than in San Francisco. “All these events are with really big groups,” she says, noting that it would be strange if an investor she didn’t know personally asked to meet for dinner one-on-one. “It’s like reading regular people. And I think everyone is very conscious of it.”
You get asked probing questions
Kristin says some of her worst experiences as a woman in VC have been in job interviews, where she often had to field questions that she felt a male candidate would not have been asked, or questions that were simply inappropriate. Since Kristin’s middle name is her mother’s maiden name, she appears to have two last names on her resume. In one interview, she was asked a veiled question about where her family was “originally from”—an attempt to figure out if she was married. When she shared the experience with male friends, they didn’t think it was a big deal. “But if you ask any woman,” she says, “they’re like, ‘Well, he’s just trying to figure out if [you’re] married and going to leave anytime soon to have kids.’” In another instance, she was outright told, “There’s a thousand questions I wish I could ask you, but HR tells me I can’t.”
During the interview process, it was clear to Kristin that many firms wanted to bring women onto their teams—but they weren’t laying the groundwork to attract and support those potential hires. “It was an interesting time to be interviewing because a lot of funds were very focused on trying to hire a woman,” she says. “They were self-aware enough to recognize that they wanted to diversify their team, but I don’t think they had the EQ to actually effectively talk to those people.”
You get interrupted frequently or talked down to
Since Kristin currently works at a fund that is female-run, she tends to confront more bias from founders rather than fellow investors. “I see it more in a lot of the initial calls we have with entrepreneurs,” she says. “The way that it usually manifests is that they’ll talk over you, which makes it hard to break in and ask questions.” In other instances, she’d ask a specific question, and a founder would respond as if she didn’t have a grasp of the business. “The assumption is always that by asking the question, there’s something that you fundamentally don’t understand—when, really, you’re just looking for a very specific piece of information,” she says. Kristin sometimes found that was also the response when she’d pass on companies; instead of just accepting the news or asking for feedback, some founders would argue she didn’t “understand the business.”
The New York-based VC says that her biggest source of frustration is being interrupted or talked over in meetings—something she has encountered with founders. One founder, she says, interrupted her “all the time,” and eventually, her male boss spoke up on her behalf. “My boss had to say, ‘Jesus, let her finish her sentence,’” she says. “And on the one hand, I’m so thankful, and I love my boss . . . but it’s just frustrating. It feels like your dad has to stick up for you.”
Still, she adds, her boss did what she believes male allies in the workplace should do. “I think the role of male advocates is really interesting,” she says. “And I think my boss does a good job of being a champion, and not being pedantic.”
*To maintain anonymity, we used pseudonyms.
Tory Burch is a woman you would probably describe as ambitious. But for years, even well after starting her eponymous brand, the fashion entrepreneur steered clear of the word.
“The first article that was written on our company was written by the New York Times,” she said during a session at the Fast Company Innovation Festival last week. “A dear friend of mine called me up and said, ‘Nice article, but you shied away from the word ambition.’” In fact, when she was asked if she was ambitious, Burch remembers finding it a rude question. “It was a pejorative and negative,” she says.
For Burch, who grew up with three brothers, gender didn’t necessarily feel like an issue when she was younger. “My parents raised me thinking I could do just what they could do,” she said. The negative framing of women’s ambition was something she started feeling as she moved through the workplace—and as she launched her brand in 2004. “When I started the company, a lot of people weren’t doing startups,” she said. “So people sort of patted me on the back and said, ‘So cute, you’re [starting] a company. Oh, and you want to have a foundation be part of it?’ They just thought that was charity work.”
Over time, Burch realized she wanted to change the narrative around women’s ambition—and help women name it. “A year and a half ago, I sent an email to a lot of people that I admired and said I was doing a public service announcement,” she said. “And it was to really deal with the word ‘ambition’ and the negativity around it when associated with women. We had to get rid of that.”
That effort became the #EmbraceAmbition campaign, which spawned the first Embrace Ambition Summit earlier this year. “We dealt with ambition, unconscious bias, and stereotypes, so it was a big idea and big words to deal with,” she said. “But I think we made some progress, and I think for women to own their ambition and be proud of it is a great first step.”
Whether or not she used the word “ambition,” Burch has sought to support female entrepreneurs—and their ambitions—since 2009, when she started the Tory Burch Foundation. In the 14 years since she started her business, Burch says, the support networks for women entrepreneurs have become far more robust, especially as the sheer number of female founders has increased (and those entrepreneurs are, in turn, able to invest in other women).
Burch hopes to keep building on those networks through her foundation. “One of the great things about our foundation is the peer-to-peer mentoring,” she said. “Eventually, we want to take it further; we want to have chatrooms and do interviews on those chatrooms. But it really has changed a great deal.”
And why is that? “People are more accepting of women in business,” Burch said. “We’re not there yet—I want to be careful because we have a lot of work we have to do. But it’s on the right track.”
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