Impress the Algorithm. Get $250,000

Ashley Carroll has a go-to story that epitomizes how grim things are for female entrepreneurs trying to raise money in Silicon Valley. Earlier this year, Carroll, a partner at the $2.5 billion venture firm Social Capital, was coaching a female startup founder ahead of a meeting with a potential investor. Let’s call the founder Jane Disruptsky and the investor John Ventureman. The pitch session seemed to go well, but afterward, while Disruptsky was waiting to hear whether the fund would back her, Carroll received a screenshot of a private text-message conversation someone else had had with Ventureman.

Ventureman began by praising Disruptsky’s startup on its merits. The gist, Carroll recalls, was: “Great business. I love everything.” Still, he was passing on the deal. The rest of the text chain read like an assessment of a blind date: “She didn’t seem warm,” for example, or, “She was just all about the business.”