“The new C.E.O. would say the same things as I did, but he swore more,” says the entrepreneur. “He made a lot of mistakes, but they were all forgiven.” Like others interviewed, the C.E.O. was reluctant to have her name used for fear that being seen as a complainer could hurt their current or future efforts to raise funding.

“There are some who have talked to people about bad experiences that they have had, and it comes back to bite them when they come back to try again,” says Springboard’s Millman.

It’s tough to dispute that the VC community is a tight-knit group of mostly men, which can lead to inadvertent prejudice when it comes to funding. Among the ten largest VC companies in the country by assets managed, for example, only about 11 percent of the partners and managing directors are women.

Venture deals require networking, and it’s harder for women to break into the network, even if they’re talented and do their homework, since the network comprises mostly men.

“For all the VCs I’ve talked to in my career, I have yet to talk to a woman VC,” says Liz Cobb, C.E.O. of Makana Solutions, a sales software company based in Lexington, Massachusetts. Makana is the third company Cobb has founded and the second for which she received venture funding. “I look at all these VC Web sites, and I look at the partners, and they’re almost all men. It’s very rare that a woman is doing the investing.”
 
Diane Hessan, the C.E.O. of corporate networking company Communispace, agrees that the venture capital industry can be like an old boys’ network. Her company secured VC funding in 2000 but only after a prolonged search.
 
“People are more likely to invest in people they know,” Hessan says. “If you have friends and business colleagues and a network of VCs, then you’ll get a meeting. If you don’t hang out with VCs and don’t have them in your network, then…the probability will go down.”

Advisors counsel female entrepreneurs to not let the extra challenges they face bother them, and just focus on their strengths.

“I counsel young women, and I tell them I really believe you have to ignore it,” says Venetia Kontogourgis, the sole female managing director at venture firm Trident Capital, who also has experience founding a company. “Just smile, and move on, and keep going. Otherwise it gets into your system.”

Zipcar’s Chase has taken Kontogourgis’ advice to heart, moving on to found a new venture—a rideshare company called GoLoco—and says that she’s having a much easier time with funding than she did at ZipCar. People know who she is now, and her previous experience helps a lot.

“[VCs] look at proven leaders,” says Communispace’s Hessan. “That’s not whether you have done a good job managing a company before, it’s whether you’ve successfully built a business in the past successfully. And guess what? The people who have done it before are mostly men.”