Natalie’s Journey: From Male CEO To Female Trailblazer

Natalie’s Journey:

From Male CEO To Female Trailblazer

This article was first published on 6/17

Just a few years ago Natalie Egan was living the American dream, as Nathan Egan, a father of three married to her college sweetheart. Chief Executive Officer of a growing tech company, Egan, as Nathan, had everything a successful business and family man could ask for, even a white picket fence.

“I spent the large majority of my life as a white man of privilege with access and resources,” says Egan. “I very much lived in a bubble but I had no idea how isolated I was from the rest of the world’s reality. For sure I thought I understood diversity, I thought I understood the struggle, [but I really didn’t].”

Fast forward to now, Egan is a proud transgender woman, and the founder of Translator, a unique tech platform focused on creating corporate cultures of inclusion and empathy. Egan spoke to SWAAY about business, her amazing journey to self-discovery and how her transition ultimately saved her life.

Natalie Jane Egan

“When I came out as a transgender woman it was this wake up call,” she says. “I knew it would be hard but I had no idea how bad it would really be. I felt bias, discrimination and hatred for the first time. I thought I knew what those things were, but when you really feel them for being who you are, it changes everything.”

Egan says that she has always known she was different, but never fully understood why she felt that way. Looking back to her childhood, Egan realizes there were clues.

“I wanted to do things that girls do, but I didn’t even really understand that,” says Egan. “I just knew I wasn’t allowed to. Once when I was five years old, I snuck into mom’s closet, put on her pantyhose and I got caught. It was mortifying.  I was so scared that my brothers and dad would find out, and I swore to myself I would never do that again. So, the first affirming memory of my gender was based on what I was not allowed to do. That really set the stage for the rest of my life; always modeling myself after what people wanted me to do.”

After attending top notch schools (Egan is a Cornell graduate) and working hard to be successful in business, Egan, as Nathan, was entrepreneurial and success-minded. With a brother and father who served as Chief Executive Officers at major pharmaceutical and tech companies, Egan was drawn to brand building and business development, and subconsciously making everyone in her life proud.

“I had entrepreneurship in my blood,” says Egan. “I always aspired to run my own business, so I built my life that way. In 2008 I landed at LinkedIn as sales rep number 11.” After the economy crashed in 2008, Egan says she became passionate about the company having a training and services arm to its business. Next, Egan met with LinkedIn founder, Reid Hoffman, and pitched the idea.

“He loved the idea but said he wasn’t going to do it because services don’t scale,” says Egan. “I thought ‘I’ll show you. I’ll make a huge business out of this.’ Although there were some challenges, Egan went on to launch a third party LinkedIn app called PeopleLinx, which took off growing from two to three employees to 45 in just 18 months. Additionally, Egan took the company from $10,000 a month in revenue to a nearly $5 million trailing run rate.

“At the peak of my male existence, I thought I had everything,” says Egan. “I was married to a beautiful woman, who was my best friend from college. We had three beautiful kids. We lived in a house with a white picket fence in suburbs of Philadelphia. Everything was perfect and then all of a sudden, the wheels came off and I started to go sideways. Part of that was my personal life; I had been hiding my identity for 38 years and it was starting to become an issue distancing me from my wife. We were both in denial about even exploring it. I was so afraid I was being recorded [while cross dressing] and was afraid I would be blackmailed. I lived in a lot of fear.”

Just as Egan began exploring the side of herself that she had repressed for the bulk of her adult life (as Nathan), a bomb dropped in her professional life.

“LinkedIn  revoked our APIs and our access to their data, and it sent the entire company into tailspin,” says Egan. “All of a sudden we didn’t have a product anymore. My employees were panicking, the investors were freaking out, and they were all freaking out to me. I had bootstrapped the business and grown it out of my basement and was starting to scale. And all of a sudden we were in a really bad situation. Plus, things with my wife were not good at all. So that hit me really hard. It was a left, right blow. Literally I was at the top of my game then all of a sudden I was on a downward spiral and it just got worse and worse.”

“I’m in process, and I always will be. Sometimes I have trouble leaving my apartment because I am worried how I will be perceived that day; Will I be attacked on the subway? That’s a hard pill to swallow but I look at everyone else who does this everyday and realize this is my calling.”

Natalie Egan speaking to a crowd about the importance of authenticity in business

Egan stepped down from the CEO role, becoming instead head of product and head of sales, putting the company’s Chief Operating Officer in charge of the company. At the time, Egan was focused on rebuilding a marriage that was falling apart and being there for her kids. Eventually, the CEO fired Egan from the company, which sent her further into depression.

“I thought my life couldn’t get any worse and that’s actually when I figured out that my deep dark secret that I was a cross dresser, was actually much more, and that I was transgender,” says Egan.” All of a sudden I realized, I was actually a woman inside and it scared the shit out of me. It was not a welcome realization. I thought if I come out it becomes everybody’s burden – my kids, my family, all the professionals around me who had invested in Nathan. I thought I have to be Nathan.”

Translator offers "empathy workouts" via an app

It was in this darkness that Egan said her thoughts actually went to suicide. “I nearly killed myself,” she says. “I didn’t want my kids to have a transgender parent and I just wanted to make it easier for everybody else. Thankfully I didn’t but I was damn close. I had a plan. I was going to do it. But fortunately, as I started to tell people about my identity, they were incredibly supportive.”

Egan began reaching out to friends, and getting a reaction that surprised her. “The response was ‘you have to be you,’” says Egan. “I slowly started to build the courage to tell my story more and more. I found that the more detail I shared of my story, the more likely it was that I would convert somebody or to create a little more empathy and sympathy for my situation and my new community. It was actually details made it real for people.”

Egan says despite the supportive reaction from those who knew her, she still faced negative backlash for being herself, like being turned away from stores and completing business transactions with employees who wouldn’t look her in the eye. It was this experience that inspired Egan to think creatively about how to foster a more respectful environment not just for transgender population, but also LGBTQ, women, and minorities.

“I never experienced how unbelievably disrespectful [people could be],” says Egan. “That’s when it started to become real to me that I needed to somehow become part of changing all of this and then it occurred to me that I’m uniquely qualified to [lead the charge]. As a technologist and an entrepreneur, it was kind of exciting to think about tackling a problem so big. I became obsessed with helping people understand other people, because they certainly wouldn’t judge me if they understood everything I’ve been through to get to this point.”

And so in early 2016, Translator was born. Described as an “empathy software company,”  the platform utilizes tech-based storytelling to help employees to embrace diversity and authenticity.

 “We start with self awareness and then work through the pillars of empathy over time, the same way you develop muscles,” says Egan. “There is a ripple effect. By working with thousands of employees in a company we are affecting all the relationships around them. If we can make someone a little more empathetic it can actually save someone’s life.”

The company, which is comprised of full-time employees and contractors, has raised $850,000 as of 2017. Although she cannot name her clients, Egan says they include Fortune 500 companies including banks, and top special service firms.

“It’s very unique what we are doing,” says Egan. “People are immediately drawn to it  because with everything going on in the world, they feel like diversity is under attack and are looking for ways to counter that and invest in it. Diversity equals talent. You need to have a diverse candidate pool in order to solve today’s most challenging problems.”

Belisa Silva

Belisa is an editor with more than 10 years of experience. Prior to SWAAY, she worked as freelance writer, covering lifestyle, fashion and beauty industries. Belisa was a Market Editor at Women's Wear Daily for five years, where she interviewed rockstar business women like Drew Barrymore, Jennifer Lopez and Iman. Belisa also contributes to Cosmetic Executive Women, where she highlights female executives making an impact in the beauty industry.

  1. You are so strong to become your authentic self. I am 58 now and ever since I can remember wanting to be a girl
    I used my maculine fascade to
    repress who I was internally.
    I was my father’s little man even though he knew about my cross dressing as a little boy.
    I wish I had had affluent parents who could have raised me to be the girl I had always wanted to be! Today being transgender is more acceptable thankfully!
    Shay Linn

  2. Thank God for your bravery in embracing your mental illness. Gender dysphoria is a nothing to be ashamed of. God bless you on your journey to recovery!

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