Wait, is this a date? Horror stories from female investors working with a male founder

For some female investors, meeting with male founders can mean weathering unwanted advances or pointed questions about their role and experience. 

Wait, is this a date? Horror stories from female investors working with a male founder
[Photo: Clem Onojeghuo/Unsplash]

When people talk about the sometimes knotty relationship between entrepreneurs and VCs, they usually point to female founders and male investors. But being a female VC presents challenges on both ends—from their male investor peers and the pool of (largely) male entrepreneurs they may work with.


Some female investors we talked to said they hadn’t faced much explicit harassment or discrimination, or that it usually came from investors, not entrepreneurs. But for others, cultivating relationships with male founders sometimes meant taking business meetings that turn into unwanted dates, or weathering pointed questions about their role and experience.

Founders may doubt your experience

Sheila*, a VC based in Chicago, finds that male entrepreneurs don’t necessarily underestimate her or treat her differently solely because of her gender. The bigger issue can be her experience, especially as someone whose tenure in venture capital is only about three years. Of course, that also has to do with the venture capital boys’ club. “Generally, the bias from the hotshot [founders] that I’ve noticed is not gender-related,” she said. “It’s more tenure related . . . A lot of the best deals are still passed between the mostly male general partners at coastal funds.”

But thanks to the leadership at her fund, she rarely feels coerced or cornered into inking deals with entrepreneurs that rub her the wrong way. “The good news is that our fund has a ‘no assholes’ rule,'” she said. “If I ever feel like someone’s not a good person, the advice I’ve gotten from my partners is, ‘Life is too short—just don’t do the deal.'”

Another VC in the Midwest felt like she was able to establish good working relationships with male founders where her “gender wasn’t an issue.” Sometimes, she said, her gender was seen as a benefit if the company was trying to reach female consumers. But she noted that her background also helped legitimize her to founders. “I was from the coasts investing in the Midwest,” she said. “I had connections to Stanford and Harvard alumni networks . . . I feel like the expertise and access that I brought outweighed the fact that I was a woman.”

You may field inappropriate texts

“I text with a lot of founders,” said New York-based VC Caitlin. “I noticed all the guys on my team do it.” When she was working on a deal a few months into her current job, a founder claimed he was interested in the fund because he wanted to work with Caitlin. Following a drinks meeting, at which Caitlin’s boss was also present, the founder—who runs a 3-D printing company—said there was something he “really wanted” to ask her.

“I want to ask what your ring size is,” he texted, as per Caitlin’s recollection. “Why don’t you think about what I want? Why don’t you try to decode what I’m trying to say?” Later that night, he texted again, to remind her not to forget what he had asked. Caitlin immediately knew something was off, but she struggled to label it as outright harassment until she told her boss about the incident.


“The subtle [comments] are almost worse than the overt ones because you feel like you’re insane,” Caitlin said. “I started to feel this shame and feel like, ‘Is he even doing anything wrong? Is this okay? . . . You create doubt in yourself, and that’s what was so infuriating to me—because it feels like they’re taking away some sort of power.”

Caitlin’s firm ended up passing on the founder, though she claims it was for a different reason. “In a male-dominated industry, you don’t want to be the reason that they pass on an amazing deal,” she said.

Founders don’t know why you’re in the room

For another Chicago-based VC, some of the frustrations she felt earlier in her career are less pronounced now.”There’s definitely a lot of stuff that just continues to wear you down,” she said. “In the beginning of my career it was much more frustrating. Everyone just automatically thought I was the admin in meetings.” Still, she still finds that founders make assumptions about women in the room. “Even today, I can be with a colleague or even a group of people at the same level as me, and we’ll introduce ourselves, and the entrepreneur will be like, ‘Oh, so what is your role?’ They assume the men are investors, but they have to ask me.”

In those instances, she often thinks about whether the founder’s behavior is an indicator of how they might treat a female employee. “The worst part about it is you don’t want to bash people like that,” she said. “But then you have to force yourself to think objectively and say, ‘Okay, does this trickle down to how they treat people on their team? Or is this just because they don’t understand, or they have a bias?’ You get into such a mind manipulation trying to work yourself out of those scenarios.”

You may end up on a date

A number of the women I spoke to argued the power dynamic was still tipped in their favor as the people holding the money, but San Francisco-based VC Victoria felt that wasn’t necessarily true with founders who had no trouble attracting investors. “In some cases, when it’s a successful male founder, the power imbalance is on his side,” she said. “He already has a lot of capital—so it’s kind of case-by-case, depending on how hot the round is.”

When Victoria launched her own fund in 2014, she had multiple encounters with male founders that were intended as business meetings but did not end up that way. “I hustled to get deals, and I think you need to have that personality to succeed in venture,” she said. One time, she reached out to an ex-Google founder and asked to grab coffee. “He immediately suggested drinks,” she said. “And he ended up pushing out [the meeting] even later, past 7:30 p.m. It was immediately obvious he wasn’t interested in [my fund]. It was very clear he was treating it as a date.” She said the founder even tried to kiss her. “It was very clear he felt the power dynamic on his side, and the meeting was not a business meeting,” she said. “I made it a policy not to meet with male founders after 6 p.m., unless I know them extremely well.”


Like other women I spoke to, she said things improved once she was a bit older and got married. “When you’re younger, you think, I guess this is normal?” But the fact that networking and meetings frequently took place over drinks meant some men could capitalize on the social context of those events. “I didn’t drink in college, and when I moved to the Valley, I realized that alcohol is such a big part of the ecosystem,” she said. “A lot of these social events revolve around drinking, which definitely introduces that ambiguity . . . It’s not necessarily a business context. It’s a gray area.”

Jennifer, a New York-based VC, said that gray area means some men steer clear of female investors at a happy hour or networking event. “You’re inherently unapproachable at these things because there’s sexual tension,” she said. Like Victoria, Jennifer has also worried about how an entrepreneur may perceive a one-on-one meeting. “I’ve been offered, ‘Come by our studio, i’ll give you a private tour of this thing,'” she said. “And it’s really hard to discern intention sometimes.”

She has had to ask herself similar questions at networking events, where it seemed like men were hitting on her or treating her like a date. And when she talks to founders at those types of events, it can sometimes feel like they would rather be talking to her male colleagues. “For an industry that prides itself on innovation, people are not trying to meet founders in creative ways,” she said. “I can’t say remove alcohol from it entirely, but women are at an inherent disadvantage in that setting.”

*To maintain anonymity, we used pseudonyms.

About the author

Pavithra Mohan is a staff writer for Fast Company.