Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.
It was around age 15 when I starting to have conflicts with my mother. Most of our fights revolved around what I was wearing. My wardrobe tended to be a little flamboyant. My clothes were too tight and that wasn’t how my parents thought a boy — their son — should be dressing. But I figured if I bought my own clothes, they couldn’t say anything. So I worked every job I could in order to pay for the things I wanted.
I was born in Kenosha, WI but was raised in Racine. I have a bunch of half-siblings but grew up in a house with just my mom, my stepfather, and my younger brother. We had two working parents, but we were still strapped for cash. We had two cars, but that was so they could both get to work. My first job was at Arby's. After that I did some telemarketing. I also worked at Burlington Coat Factory. I understood the value of a dollar really early on.
I graduated high school when I was 17 and enrolled at the University of Wisconsin, Parkside. But I really, really, really wanted to study music and theatre. I learned how to play piano by ear in the fourth grade. I sang in choirs. I wrote my own songs. But my journey is very much like Lauryn Hill’s character in Sister Act 2: Back in the Habit when Sheryl Lee Ralph says to her, "We don't need you singing your shoulda, coulda, wouldas on the corner." That was pretty much the exact same speech I received from my stepfather.
My stepfather’s experience as a black man has shaped his worldview. Growing up he would tell me, "Being black you have to work four times as hard as everybody else to get ahead." He would say, "You have to run your own company in order to be able to make your own decisions. Study business,” he’d tell me. “Otherwise you're gonna be poor.” And I listened because being poor and black is not the look, you know?
So I stayed living in town and my stepdad paid for my first semester of college. But it wasn't working out for either of us. I wasn’t happy and he was like “I can’t afford to do this.” And I didn’t want to pay for something he was forcing me into. And that’s when I decided to enlist in the Navy. I was 17 so my parents had to sign a waiver for me join underage.
I joined thinking I would get the GI Bill and receive money to pay for a degree I actually wanted. I moved to Rochester, NY and then was stationed in Yokosuka, Japan for four months. I really didn’t know I was trans at the time. I was just really confused. “Don’t ask, don’t tell was still in effect and I couldn’t really trust anyone to talk about who I was or what I was feeling. I knew I was feminine. I knew how I felt. I just didn’t have the terminology for it. I was quiet about it, but that didn’t stop the death threats.
I was discharged from the Navy in such a violent way. Some guys hung me out of a third-story window to try to get me to admit I was gay. My life flashed before my eyes and I immediately knew I had to get out of there as quickly as possible and start living my truth. So I went to the attorney's office and they told me there was no sense in fighting the military because they just protect their own. They basically told me the only way to get out was to admit on paper I was gay. So I took their advice and promised myself as soon as I got back on American soil I was going to start living life on my own terms: as a woman.
Leaving the military was so bittersweet. I was saving my own life by leaving. But I left feeling so disappointed in this country. I remember thinking to myself that the freedom I was fighting to protect wasn’t meant for me. I'm actually still fighting my discharge in order to get the benefits I rightly deserve.
After leaving the Navy I moved back to Wisconsin to live with my parents, where I met Traci Ross, a queen in Milwaukee who ended up being my drag mother. She’s where I got the last name “Ross.” She also helped me get on hormones and start my transition when I was 19.
I have a great relationship with my parents now, but when I first told them I was trans they kicked me out of the house. After that, I went to live with my birth father — who I had no prior relationship with, mind you — in Roanoke, VA. He seemed to be more accepting of me, but really he was just looking for a roommate to help pay the bills — which I did with my tips from waitressing at Applebee’s. I used the money that didn’t go towards rent to put myself through cosmetology school.
I worked on and off at Applebee's for like, six years, but was eventually let go in a really shady manner. I don't know how I managed to get the job as a trans person in the first place, but I did. When I applied I put down my driver's license and the gender marker was male. I remember, very vividly, I had a shaved head in my ID photo. It was a very masculine picture. But the manager was so clueless. I remember him asking me if the name on my license was my legal name. I was like, "Yes, but the name on my application is preferred." He was like, "But your father gave you this name? That's a weird name for a daughter." My secret eventually came out and I was stuck working in a very toxic environment.
Performing at a drag bar is like winning the lottery to work in a sweatshop.
During one of my shifts, another waitress called me by my birth name. We ended up getting into an argument and I, in a very joking way, picked up a butter knife and said, "Bitch, if you call me by that name again I'm gonna cut you." It was very campy and everyone started laughing, but I was just trying to deflect and redirect the discomfort I felt over her using my dead name. All of the sudden I found myself in a meeting with the regional manager and he was like, "You know, we can't tolerate violence." And I'm like, "You do not have the entire story. What happened to all of the complaints I made about being sexually harassed? About the dishwasher exposing himself to me? Or about my coworkers calling me horrible names?" And he just looks at the manager and says, "I never heard about any of those things."
After that, Applebee's offered me all kinds of shining recommendations for any job I wanted – elsewhere. I just couldn't work there anymore.
I was introduced to a woman who was making all kinds of money running an adult website. And that’s when I learned about the sex trafficking of trans women. And I say sex trafficking because there’s often a level of high coercion in getting girls involved. Recruiters will say, “Where else can trans women work and be paid as much? Let alone be treated like a human being?” And the sad truth is, they’re right. That’s how a lot of girls start doing sex work. For many, it’s not just a way to make ends meet; it’s a way to affirm their identity as women.
I didn't want to do any of that, though. Sex work just wasn't my lane. But I was damn good on the computer. And in a stroke of serendipity, the woman needed someone to help run her website. So I moved to Florida to be her webmaster. Eventually, I left to create my own adult website. I did that for about six months or so.
I lived in Boca Raton with my ex from 2001 to 2006. We were engaged and he helped me get my real estate license and I started making money that way. I also found a modeling agency and signed with them. They did not know I was trans. And so I started doing commercials. I did runway. I modeled in jewelry catalogs and eventually ended up acting in this foreign film called Natale a Miami which means Christmas in Miami. And it's sort of like Italy’s version of National Lampoon’s Christmas Vacation. So I was in this random foreign language film that became this blockbuster hit in Italy — it was beating King Kong at the box office at one point — while also selling houses and using that commission to pay for my tuition at Florida Atlantic University, where I was finally able to study theater and creative writing, before ultimately dropping out my junior year. I had to leave school when shit really hit the fan with my relationship.
My ex had asked me to keep my trans identity a secret because we were living in one of the most conservative, white spaces in America. But I was tired of living in stealth. I asked him to move to Chicago with me where I could find better work and spread my wings. He refused. So I gave him back the ring and went on my own.
When I got to Chicago I started performing at the Kit Kat Lounge, and let me tell you, this is whole other piece of my financial puzzle. It’s a great example of how trans women around the country are being marginalized and oppressed by members of their own community. We are taken advantage of by the gay, usually white, men who own the clubs where trans women, femmes and drag queens perform. Almost none of these places pay. Performers have to work for tips. And if a girl makes it known that she’s not willing to dance solely for tips, the owners will just get a new girl to come in and do it instead. There are only a few places — the Kit Kat Lounge being one of them — where there are a handful of cast positions. And if you’re lucky enough to get on cast it means having somewhat consistent pay to count on week to week. But the pay is under the table. And the boss makes it a point to remind cast members they’re highly replaceable. So it's like winning the lottery to work in a sweatshop.
The competition for cast positions has gotten worse in the age of RuPaul's Drag Race. Now most girls can't get a paid gig to save their life unless they’ve been on that show. But even if you manage to secure a steady gig, there’s really no long-term benefit of working at drag bar. You’re not contributing to a 401k. You’re not receiving medical.
It’s hard for trans women to find financial and medical security. That’s why I went with some Latina girls to Ecuador to get my boobs done. I saved thousands of dollars and didn’t need proof of health insurance. Luckily nothing went wrong. I’d have been screwed if there were any complications, but that’s the risk I took. I’m actually currently trying to nab a date to undergo the rest of my surgeries in Thailand because I still don’t have health insurance. And in Thailand I don’t have to jump through hoops to get a letter approving my gender reassignment surgery. Here in the states I have to prove to someone I’m good and ready. But, like, why should I? I’ve been on hormones since I was 19.
I left Chicago and moved to LA in 2010 and that's when I started working for Apple at one of those stores that had a huge theatre in it. I’m telling you, I’ve done it all. I would wear a headset and stand on a stage and teach people how to use different software, all while running a company I started where I would offer clients a whole bunch of creative services. I designed everything, from backstage passes for Cedric the Entertainer and Ludacris to CD covers for independent artists. I also produced photo shoots, did some retouching work and even built websites for people. All of which I taught myself how to do online by watching videos on this site called Lynda.com. They have a lot of really great video tutorials.
After two years in LA, my résumé was looking good and I moved back to Chicago to take a job at the Trans Life Center as their employment coordinator. They had this job readiness program where trans individuals would receive a safety and sanitation license to work in restaurants. It was well intended, but the program was basically ushering people into jobs they didn’t want instead of teaching them skills that afforded them more options.
That was my introduction to the non-profit, social work sector. And it's where I learned how to steer clear of discriminatory hiring practices. No one knew what I looked or sounded like. All that mattered was my skill set. If I could do the work, the job was mine. And that’s what inspired me to start my own non-profit. In 2014 I launched TransTech Social Enterprises, a talent incubator focused on economically empowering trans careers. I moved to DC, where the Human Rights Campaign heard about my mission and gave me office space at their headquarters completely free of charge.
I raised $10,000 to help launch TransTech through an online fundraiser. Then MillerCoors matched that. So I had $20,000 to operate our training programs. There was no salary for me. In the four years I’ve been running this company, I still have never taken a salary. There was no salary for a staff either. So I found some volunteers and literally slept in the office. My credit score tanked. My bills weren't paid. But I began training people in all things tech and was eventually able to attract more funding by charging for the services we offered — having the girls who came through the program build websites and apps and platforms for outside clients.
I got to a place where every white person in every white organization in DC started inviting me to their galas and panel discussions and to all these things that put my face — my black trans face — front and center within their spaces. I even made relationships with the White House. And everyone would pretend to think what I was doing at TransTech was brilliant. But the moment I would start talking about fundraising, I cannot tell you how quickly and often people would suddenly be like, "So, explain all of this to me again? I'm not quite getting it." Isn’t it funny how that works? So you got it when you invited me here, but now that I’m asking for actual help you’re confused?
During my entire journey, I always found time to act. I got my big break when I was in Chicago and living with Jen Richards, who wrote Her Story, which ultimately became the Emmy-nominated web series I co-starred in. It was a little passion project, but when Kerry Washington tweeted at me and was like, "Angelica, I'm your fan," I knew I wanted to do more.
Starring in Her Story was the first time I was able to be openly trans and actually bring my whole experience to the table. It was the first time as an actor I was able to just act and not have my inner dialog running wild, wondering if the cameraman was too close or if my voice was too low. I wasn’t asking myself how I’d play off being found out. My secret wasn’t a secret.
That experience is what led to Doubt on CBS. The network saw me and then cast me. I didn’t even submit for it. And honestly, that’s basically how it’s been ever since. People have been asking me to audition. It's a very interesting place to be, because I used to do any and everything to be seen. From sleeping on the concrete for casting calls to waiting in lines that wrapped around the block to auditioning for Wanna Be a VJ on MTV. I’ve gone from really going out of my way to get cheesy auditions to now, where my dreams are literally chasing me down. It's at a point right now where I actually have to say no to things.
Before Pose on FX I did Claws on TNT. I basically told all the girls — and I do mean every single trans girl who auditioned — to just go home because the role was mine. Literally every trans actress in Hollywood auditioned for it: Isis King, Jen Richards, Alexandra Grey, Trace Lysette. And they will all tell you, “Angelica was manifesting getting that role.”
Pose was something I didn’t want at first. I was like, "This is not for me." But I was getting a lot of signs from the universe hinting I would be on this show. And when Ryan Murphy met me he was like, "I want to write a role specifically for you." So I signed on and Ryan has been incredible. I didn't really have a big role to begin with, but he’s a director who gives actors some freedom. He was asking me to ad-lib one day and then he asked Janet Mock to write an entire episode for me the next.
Waitress. Makeup artist. Realtor. Dancer. Web Master. Actor. I've worked every kind of job you can think of. So when I talk about my value you can trust I’m worth every penny.
As told to Maxwell Losgar exclusively for Wealthsimple; transcript edited and condensed for clarity. Illustration by Jenny Mörtsell.