“Many women navigate what I call ‘perception gaps,’ being underestimated or typecast based on their past roles,” says Laura Huang, a professor and associate dean of executive education at Northeastern University. “After an exit, they may feel pressure to prove what’s next, especially if their identity was deeply tied to their company.”
She explains, “Even after success, women often experience ‘success guilt’ or feel the need to justify further investment in themselves, especially if caregiving or cultural norms are in play.” Going after an advanced degree can help with this feeling by allowing women to “reposition themselves” and “reset” after an exit.
A common concern shared by these founders when deciding to return to education was falling behind in their industries. “The tech world is changing so fast right now that the pressure also comes from feeling that if I don’t go back into it immediately, I will get irrelevant,” says Shruti Kapoor, another Y Combinator alumna who founded Wingman, which was acquired by revenue operations company Clari in 2022.
Heading to a brand-name institution can be a way to counter some of the challenges founders realized they faced on their first go-round—before potentially starting a second company. “I think that my path would have been easier as a founder raising money had I had a fancy brand name institution on my resume when I started out,” says Hayley Leibson, founder of generative AI startup Astrapilot, acquired by Blackhawk Systems founder and CEO Robert Spix in May 2024. She is now pursuing a master’s degree in management at Harvard.
It depends what a founder wants to do next. “If the women wanted to go on a corporate board, people might like to see an MBA,” says Siri Terjesen, associate dean, research and external relations and a professor of entrepreneurship at Florida Atlantic University, “because you can’t always exactly explain what your startup experience really was.”
Nina Ajemian
