Corporate Transition

When presenting as a man, this “tech bro” entrepreneur was the toast of Silicon Valley—until she stepped into boardrooms as a woman.

By: STEPHANIE CLIFFORD  - OCT 14, 2021

Natalie Egan
photographed  July 2021

Back when entrepreneur Natalie J. Egan was a self-described “bro,” when sports metaphors rolled off her tongue and she tossed Frisbees over employees’ desks, she walked into a board meeting of the tech company she founded, and brought along a scorecard—not for her, but for the board members. “‘I’m gonna create a scorecard for all the people on the board, tallying all of the things you do quarter by quarter to help me in the company, [like] who you’re introducing me to,’” Nate Lentz, managing partner at Osage Venture Partners—one of those board members and an investor in the company—recalls Egan saying. “Which…we hadn’t really seen before.” “Am I remembering this correctly? Was there a promise of a trophy to the winner?” adds David Drahms of Osage, a board observer. Lentz bursts into laughter. “I think there was.”

That was circa 2009, when she was “an asshole and a jerk,” Egan says. But that wasn’t the only thing that was different about Egan back then: She had been assigned male at birth and raised as a boy. Married with three children, Egan took pride in her college-frat bona fides and harsh management style. She was a tech bro—a successful one, raising $7 million in investments for the tech-sales company she founded. Sure, it was the product of hard work, but it was nothing more than she—presenting as a straight white man—thought she deserved. Or so she thought. When Egan began transitioning at 38, and started a second business as a woman, she was in for a rude awakening. Despite her years of experience, once she transitioned, Egan says investors didn’t take her seriously; men talked over her, and she struggled, sometimes literally, to find space at the table. “I remember being in shock, and thinking, ‘Oh, this is what women have been talking about the whole time,’” she says.

Natalie Egan being interviewed
for LBTQ Women In Tech Conference
May 2019

Decades of research has established the reality that men and women are treated differently at work, and most women can cite examples of how they’ve been underestimated, passed over, or underpaid. Egan is likely one of the few people who’ve run companies presenting as both a man and a woman. (Trans identities, of course, include a wide range of gender identities and expressions, including people who identify as gender-nonconforming or nonbinary, people who go through medical and social transitions, and much more.)

There aren’t solid numbers on how many transgender entrepreneurs there are in the U.S.; according to a 2016 study by the National LGBT Chamber of Commerce, over 900 small businesses qualified as being majority LGBTQ-owned, of some 28 million small businesses overall. Of those, about 2 percent were trans-owned. While that likely far underestimates the number of trans business owners, Egan’s experience is rare. Presenting as a man, “I had so much privilege that I didn’t realize. When I thought I was getting knocked down, I wasn’t really getting knocked down, relatively speaking,” says Egan, 44. “It’s nothing like what other folks in the world experience who don’t have the amount of privilege that I had as a white, very masculine-presenting person.”

Read the whole article as it appears in the October 2021 issue of ELLE...

Talking one-on-one, I ask Egan how she felt after that first glimpse at what starting a company as Natalie looked like, when those VCs rejected her. She sighs, and suddenly looks very tired. “I really believed, probably because of my naïveté about my previous success, that I would be able to bulldoze my way through that. Like, I’d be the exception; I would win.” Now, having experienced the business world as a trans woman, she thinks differently of people who have struggled: “It’s like, ‘Can I walk in those people’s shoes, and understand what it’s like not to have the advantages I always had?’” And through her own struggle, she says:

I’ve become who I always really wanted to be.

Personal Note: Thanks to Sylvia for sending along the link to this article.