I had spent a third of my time worrying about not being authentic. And when that was gone, my mind became so clear.

FAVORITE AUTHOR OR BOOK: Rebecca Solnit “A Field Guide for Getting Lost.” FAVORITE DISH: A hearty but low calorie soup. SOMETHING THAT MAKES ME GO "AWW": My wife’s smile. SOMEONE I ADMIRE: Robert F. Kennedy.

Michele Bettencourt

Forgiving everyone before you can forgive yourself

INTEGRATING COMPANIES, BUT THE SELF REMAINS FRAGMENTED. Michele Bettencourt introduced herself to the staff and employees of Corelight, a network cybersecurity firm, as the new executive chairperson. She then listed her qualifications, which were extensive—CEO and chairperson at cybersecurity firm Imperva, board member at cybersecurity firm Proofpoint, CEO and director at code analysis software company Coverity and CEO at three other companies.

It was an impressive resume spanning nearly 30 years of executive leadership experience. Michele then revealed that if anyone were to look up her those positions, they would have been under a different name—Anthony—one that she used prior to transitioning to a trans woman. The staff welcomed her warmly, which Michele says she’s still trying to get used to. “My life has gone from closeted and trying to figure out who I want to be, to shockingly welcomed.”

In 2016, Michele was having a discussion with an investor at Imperva about due diligence, when the investor suddenly said to her that he knew her secret about her gender identity. He then outed her to the board of directors. “Did you know your CEO is transgendered?” Michele recalls him saying.

In a whirlwind, the board started bombarding Michele with questions. “I felt violated. It wasn’t showing transphobia they were showing, but they were nervous I couldn’t get the job done,” she says. They had invested $140 million into the company and were worried about their investment. “It would have been easier to accept if they just told me they hated trans people, but no, they said we got to guard our investment, as though I was suddenly incapable of leading the company,” she says. And that was Michele’s ramp off the company.

THE WORLD CAN BE KIND. Since Michele’s transition, she has been dedicated to mending her life. She strengthened her relationship with her wife, and took steps to resolve her anger with her mother. She channeled her energies into creating music and her own documentary, “Beautiful Lie.” She sat on the board of trans organizations.

In early 2019, Michele got an email from a headhunter about Corelight. She dismissed the outreach as it was sent to her old email address, associated with her dead name. The headhunter said the investors knew about her story and would like to speak with her. Michele told them she was going to send them her documentary, and if they couldn’t stomach it, they should stop any further conversation.

“Every response I got back was ‘You’re brave; you’re courageous,’” she says. Michele kept pushing back. You don’t want the blowback for having a trans person as a chair, she told them. And a board member told her if an employee has a problem, maybe the employee is wrong for the company. And if a customer has an issue, maybe the customer is wrong for the company.

Order your own copy of the Gaingels 100, today! Our mission is to encourage greater representation and create a more diverse, equitable, and accessible venture capital ecosystem. Elevating the stories of the most inspiring amongst us is one of the ways in which we do this.

Gaingels 100 2023
Lead Image
1st Edition

Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.

Gaingels 100 2023