- Natalie Egan is an entrepreneur who founded two tech startups.
- She says coming out as a transgender woman helped her learn empathy after she spent years contributing to a toxic “tech bro” culture.
- This is her story, as told to the reporter Cadence Bambenek.
This as-told-to essay is based on a conversation with Natalie J. Egan (she / hers), 44, a transgender tech entrepreneur and founder. When Egan founded her first company, PeopleLinx, she presented as a man, but by age 38 she had come out as trans. By the time she was fundraising for her second startup, Translator Inc., which uses technology to help companies meet their diversity, equity, and inclusion goals and initiatives, she was shocked at the challenges she faced in her new identity. She spoke about the journey with Cadence Bambenek. Their conversation has been edited for length and clarity.
Raising capital as a second-time founder is supposed to be easy. They say the first million is hard but the second million is inevitable. When I started raising money for my second startup in 2016, I had the connections, I had the experience, I knew how to build teams and mentor people. I’d raised $7 million and built and sold complex B2B products.
So I expected that securing funds was within my reach — and I was wrong. What I didn’t realize was that presenting as a white man trumped all of the experience I had as an entrepreneur. But by 2016, I had come out as a trans woman and publicly started my transition to become Natalie.
When I gave presentations as a man, the other men in the room picked up on my energy.
They never thought about the risk, even though it’s inherent in every business plan. They could simply see my vision.
But when I gave presentations as Natalie, all they could see was risk. It was written all over their faces. With Natalie, they saw risk in the plan, risk in me as a person, as a trans woman.
I used to command the boardroom. I was very aggressive. I’ll be the first to admit that my behaviors — the ways I related to my employees or investors — verged on toxic. At the time, I didn’t even realize the power I wielded and the amount of space I felt comfortable taking up. Respect was important to me, as it should be to everyone, and I would demand it.
During one presentation as CEO for my old company, I noticed an
was not paying attention. I stopped the entire presentation and called him out for it. I realize I could never do that now as a trans woman.
Pitching to a group of VCs as a trans woman, I was ignored, disrespected, and even laughed out of the room.
Fast-forward to 2016, when, after transitioning, I pitched my new DEI-focused startup, Translator, to a similar assembly of 15 to 20 venture capitalists — a room full of more white men in suits.
During one of my presentations, an attendee was on his phone — not just using it to check messages or email, but actually talking on the phone. At first it threw me off, hearing someone’s voice during my presentation, and I assumed it was a question for me. But after pausing long enough to register that he was not in fact speaking to me, I was mortified.
It’s one thing to take a call (not great). It’s another thing not even to have the courtesy to step out of the room.
At the time, I remember thinking that I didn’t want to cause a scene. I didn’t want to interrupt him. The irony! I was just terrified that, if I reacted at all to the situation, he or the attendees in the room would think I was rude or maybe even tell other venture capitalists that I’d interrupted him and then they’d decide not to fund me.
Other times, I’ve had attendees fall asleep during my presentations or, worse, laugh me out of the room. Nothing like this ever happened to me before I transitioned.
The truth is they’ve never seen a CEO that looks like me or sounds like me. They have never seen a trans CEO be successful. It seemed like a hurdle they couldn’t get over. They no longer saw the big market opportunity or my professional experience and proven ability to execute. Instead, they only saw risk.
It was from a constellation of experiences like this that I began to understand the things women and people of other marginalized identities must go through daily, let alone when pitching for venture capital. I began to experience firsthand the harassment that’s so commonplace for many women, many of whom become desensitized after experiencing it for so many years.
Before my transition, I had neither self-awareness nor much empathy.
I used to pit my subordinates against one another. When I had opportunities to stop my team members from bullying other employees, I chose to do nothing.
I used to pat a Black employee on the head to greet her. I thought I was fostering a friendly relationship with her by giving her affection. Of course, she was never going to say how uncomfortable it made her feel, but it wasn’t until long after the fact that somebody pointed out how inappropriate it was.
I hate to admit it, but if she’d tried to communicate her discomfort to me at that time, I don’t think I would have taken it well. It’s not comfortable for a man to confront the reasons he might have power.
When I presented as a cis white man, for instance, I thought I’d earned everything I ever had. I didn’t realize that with my advantages in life, I could put in the same work and yield more every time. I just couldn’t see it at the time.
Coming out and working in Silicon Valley as a trans woman helped me realize how representation matters on every level — from the boardroom to the front lines. The research shows that organizations with diverse C-suites make better decisions, but companies are still slow to act on diversity initiatives.
But for any of us to explore and develop self-awareness and understanding, we need to feel comfortable and welcomed. With my new startup, Translator, I wanted to bring DEI exercises into the digital age. We’ve created a safe place for employees to explore and understand (for example) their own privilege and marginalization in life and allow them the space to sit with any uncomfortable feelings.
Through my transition, I became an overnight minority. Most people aren’t going to have my experience, certainly, but we’re all transitioning all the time, one way or another. I always say: My journey to Natalie was also my journey to empathy.