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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.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. 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 Power Point pitch a dozen times and met with more than 50 potential investors. They had 1,500 clients wait-listed for a beta launch.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. That afternoon, over lunch in the California sun, they committed to an ambitious business plan.

That swells to 79 or so the number found circling the giant planet since Galileo spotted the first of them with a homemade telescope more than 400 years ago.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.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.

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