Ann Crady Weiss just raised a $7 million Series A round for her second company, parenting tech startup Hatch Baby, but the money didn’t always come so easily — and she was sometimes the reason why. Ten years ago, Weiss had her first investor meeting for Maya’s Mom, a social network for moms. The meeting went well, but as they approached the parting handshake, Weiss got cold feet and didn’t ask for an investment — so she didn’t get one.

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