Meet the Vanguard: Trans Businesswoman Angelica Ross Tells All

The former lounge singer tells The Advocate how she survived sex work and a suicide attempt, found spirituality, and made peace with her mom. She's one of this issue's Vanguard.

Angelica Ross spends most of her time these days in Washington, D.C., working in an office just down the hall from the head of one of the largest LGBT organizations in the world.

Human Rights Campaign president Chad Griffin is one of two presidents with offices on the fifth floor. The other is Ross, the founding CEO of TransTech Social Enterprises, based in Chicago, and president of Miss Ross, Inc.

Ross, the 34-year-old entrepreneur, business leader, military veteran, and transgender role model, was not behind a desk as recently as five years ago.

She was onstage, entertaining crowds as a showgirl at Chicago’s Kit Kat Lounge and Supper Club.

And she was lip-synching.

“The art of what they call female impersonation, or the drag shows, really helped me to hone what type of woman I was,” Ross tells The Advocate during a break in a business trip to her old Chi-town stomping grounds.

“What did I look like, what did I feel like all dressed up, how was I sexy, for me, as a female? Over time, I got to know myself in that way,” says Ross. But her presentation, while successful, did not address the trans woman who hid underneath all that makeup, as she competed in pageants as a female impersonator. She was another one of the performers vying for a crown, singing songs made famous by another woman named Ross.

“Stop in the name of love

Before you break my heart

Think it over

Think it over”

Ross indeed thought it over.

One night in the Kit Kat Lounge, Ross came to the conclusion that she describes now as the metaphor that changed her life forever:

“I was lip-synching but I felt I was not truly using my own voice, as a trans person. I was just playing a character that was appeasing the gay community. They’d tip you dollars not knowing those dollars aren’t even going to cover the cost of the eye shadow you just put on your face to earn that money.

“Once I stepped off the stage, the gay community was not there for me. I’d walk up and down North Halsted Street, daytime or even at nighttime and I’m not seeing a single trans person serving me a drink, or ringing me out at the local gay-owned shop. None, or at least hardly none, I should say, actually employed by LGBT businesses.”

That road led Ross to stop performing and find a career. She tried her hand at beauty school, then real estate, lived in Florida and Los Angeles, and last year launched her own company: she is the CEO of TransTech Social Enterprise, a training academy and apprenticeship program.

Ross’s website describes her groundbreaking company as a tool to “empower, educate and employ the trans community through the use of technology, while promoting innovation, independence and entrepreneurship.”

Before the Racine, Wis., native became a career and leadership coach and businesswoman, even before she was a showgirl, she was on a far different path. She joined the military after high school, a move familiar to many a transgender woman, an action that she said she made contrary to how she was perceived, even as a child.

“I had always been pegged for being feminine,” Ross says. “People would always say, ‘Ooh, that’s a pretty little girl.’ They would talk about my eyelashes or that I was sensitive or that I was crying all the time. I didn’t want to play in the dirt outside with the boys.”

All the signs of her gender identity were there, but her mother either missed them or deliberately ignored them.

“If she was paying attention or wasn’t in denial around it, I think she could have been an ally to me, especially if her religion didn’t step in the way.”

After serving her country, she came out at age 19. It was 2000, “before I knew anything about trans,” says Ross.

She considered herself gay at that time. To her evangelical Christian mother, who ultimately became a pastor, Ross was better off dead than gay, and her mother took it beyond personally.

“She told me I should commit suicide or she would, because she couldn’t have someone like me as her child.”

Ross did as her mother asked, and almost overdosed on medication. But she survived, and knew she could not go back home.

Six years passed, Ross says, before she’d see her mother again. From time to time she would receive care packages — most often, food, like ramen noodles — but they rarely if ever talked.

“I’d call my mom and try to get her to accept me as her daughter, but she told me, ‘I’ll never accept this.’ It was heartbreaking.”

Although she rejected her mother's passion for Christianity, Ross says she did find strength in another form of spirituality: Buddhism.

Her mother set a tone that was at first followed by other members of her family, until her relatives one by one reached out, telling her, “Your mother does not speak for me.”

And in time, even her mother came around. But Ross says she felt compelled to reveal something she had done in those desperate and lonely intervening years, before she could take that next step with her mom.

“I had to have a very hard conversation with my mom and stepdad on the phone one night. I told them, ‘Listen, I know you want to be in my life, but I cannot move forward without telling you what the price was for me because you didn’t support me. What I had to go through,’ and that’s when I told them about the sex work.”

Like so many, Ross had used the one thing she had to survive: her body.

“This is not just me; this is what happens to so many trans people when they get kicked out of the house. People don’t want to hire us. We have nowhere to live. What else did you expect to happen? My mom predicted when she kicked me out, ‘You’re going to wind up on the streets and sick with HIV.’ Luckily I was able to escape that prediction.”

Ross looked at sex work as a circumstantial situation, to not let it define her. “‘This, too, shall pass,’ I said to myself. I had an exit plan. I didn’t stay in more than maybe a month or two.”

She put that money not just into survival but growth: getting a real estate license in Boca Raton, Fla., attending Florida Atlantic University, and starting TransTech.

Since May, HRC has donated office space to her start-up and connects Ross with its assets and resources, which has helped her land half a dozen clients.

TransTech services range from $1,200 to as much as $60,000 a year for corporations looking to learn how to attract, retain, and embrace trans employees, and to members of the community her company offers specialized training costing no more than $99 a month, and there are free services as well as scholarships and sliding scale programs.

Perhaps most surprising, given the name, is that TransTech is not exclusively for and by transgender people. “One of our members is a cis Latina lesbian,” says Ross. “She’s helped lead our team. And we have people from different places like The Wall Street Journal volunteer to do blog writing and lead workshops.”

Aside from her work at TransTech and giving speeches like the one she was in Chicago to deliver, Ross is single, dating, and once again acting in a new Web series drama about trans and queer women, called Her Story. She's also making connections where she can, including a certain trans woman named Caitlyn Jenner.

She and her friend, and former roommate, Trans100 cofounder, Advocate contributor, and Her Story co-creator and actor Jen Richards, appeared on I Am Cait with the former Olympian.

“As Jen pointed out in The Advocate, there is not just one trans movement. We have to learn to be allies to each other. We are in a deficit, of financial and social capital, and TransTech aims to help trans people reverse that.”

The other Vanguard profiles from the October/November 2015 issue of The Advocate are here.