Eight Questions for Shelby Chestnut, Executive Director of Transgender Law Center

Shelby Chestnut. Photo Credit: Onyx & Ash.

In 2023, Transgender Law Center, the largest national trans-led organization advocating for a world in which all people are free to define themselves and their futures, named Shelby Chestnut as executive director. Chestnut first joined the organization in 2017 as director of policy and programs.

Chestnut, who grew up in Montana and Minnesota, is the first Native trans executive director of Transgender Law Center and one of the first Native trans leaders to head a national LGBT organization. They have over 20 years of experience in community organizing, policy change and advocating for LGBTQ communities of color. Chestnut has a bachelor of arts in communications and cultural studies from Antioch College and a master of science in nonprofit management and public policy from The New School.  

In their role at Transgender Law Center, Chestnut oversees legal advocacy, organizing and movement-building programs that advance the rights of transgender and gender nonconforming people across the nation. Transgender Law Center’s litigation victories set precedents in areas such as education, immigration, healthcare, employment, and prison conditions.

IP spoke with Chestnut about their background, work at Transgender Law Center, and hopes for philanthropy. Here are some excerpts from the conversation, edited for length and clarity.

What do you like to do outside of work?

I like to collect things, so I have a major shoe collection and record collection. I am a huge fan of road trips and going to places that I love. I'm always scheming where I can go next. 

What parts of your personal history do you bring into who you are today?

I grew up in the ’80s in Montana and went to high school in Minnesota. My dad is Native and my mom's family is Norwegian. I feel like where you're from is a big part of your identity, grounding and orientation to the world. I've always treated everything like I live in a small town, even when I spent a lot of time living in New York City in my 30s.

My orientation is to know your neighbors, be kind to them and help people out. It’s how I got my start in organizing — getting to know people and building people power based on what the people are saying. Nowadays, things are highly professionalized, and yes, that’s real and important. And also for me, talking to people face to face about what they want and what impacts them is the very neighborly thing to do where I’m from.

What did you learn about money growing up?

I didn't learn much. I came from a poor working class family. My mother was a single mother and worked tirelessly to get me access to the things that she knew would help me succeed. A little bit of a troubled kid, I had learning disabilities, I was queer, trans, and bullied; but in retrospect, she did all the things right to get me this, quote-unquote, “access to a better life.”

The first time I ever understood money and what it can influence or buy was in undergrad and graduate school in New York City right after the 2008 recession. Everyone in grad school was 22 with their parents paying for school, and I was almost 30 paying for school myself and commuting an hour each way. 

So to be honest, I kind of knew nothing about money growing up, which I think is a real disadvantage in this day and age when so much of people's success is determined on their wealth, access to wealth, or proximity to wealth. Much of the issues I've organized around in my life are around the impacts of capitalism. It’s complicated because on one hand, you're working to increase people's access to capital wealth, and you're also fighting those various systems that control people because of capitalism. 

At what point did you understand that philanthropy was part of the work that you’re doing?

It was a little bit of an accident. I was super fortunate for much of my career to have interactions with progressive, social-justice-focused philanthropy. When I was about 25, I lived in New Mexico and worked for an arts organization where we would do these communal dinners after big art openings. I remember getting seated next to this woman and spending the whole evening just chatting her up and having no clue who she was. It turns out she was the president of the biggest foundation in the city and was responsible for a lot of the local arts initiatives. It was there that I began to understand so much of philanthropy and fundraising is building a relationship, and I was really good at that. I can chat with anyone, literally!

What role do you see philanthropy and fundraising playing in Transgender Law Center’s work?

I see our relationship to philanthropy as one of mutual need for each other, but also, I see us in a location where we can educate to increase philanthropic dollars to LGBT movements, but specifically trans movements, and I think change the course of history. Being the largest trans-led organization in the country and probably the world, we've gotten this big by doing really critical work. We're incredibly grateful to our supporters, and also, we have an obligation to push philanthropy's big picture to think about, “What's your investment in trans lives?”

I think most people are turning on the news right now and see what is happening in this country to LGBT rights, but really, ultimately, trans rights. I think we as a progressive movement need to contextualize that our opposition will always outspend us but they can't outmaneuver us. We need to get major dollars into trans-led work around the country now, immediately, like two decades ago! But if there was a year to do it, it is right now.

But we also need to understand that this is not just a trans issue, this is a social progressive issue that we're dealing with. The more we can work at the intersections of these issues, whether that's racial justice, immigration justice, criminal justice, LGBT rights, the list is endless… the better we will do at meeting this moment as progressive leaders and doers.

What is on the horizon at Transgender Law Center?

We've got some spicy things planned for what is probably going to be a really hard year for so many people around the country. We’re working on fortifying our movements through the building trans power framework we have. Our newest project launching this year is our Trans Agenda for Liberation narrative lab, with fellows around the country doing shared work on how we meet this moment collectively and put a path forward. 

We have some other things that we can't talk about yet, but I think it's going to be a good year. We're going to rely on our community more than ever, and I hope that they rely on us to think about meeting the challenges of this moment, because particularly since COVID, we've learned that our communities are resilient. They're particularly resilient if they're invested in and properly cared for.

What changes have you noticed in the philanthropic sector throughout your career?

We have more trans leadership around the country than we've ever had before. Ten years ago, there was not a trans organization in every state and I can guarantee you there probably is now. Sadly, the philanthropic dollars have not changed much. We're still at a moment where four cents of every $100 goes to trans-specific work within LGBT philanthropy. That just shouldn't be the case.

I also see that there has been a major investment in some of the litigation strategies, which is critical and important, but there is also a huge need to fund direct service for shelter, for community organizing. If we don't fund all of those collectively, then we're not going to get to the whole issue.

One area that is desperately needed for investment is narrative change. It's become a bit of a buzzword, but let's break it down: It’s power building and telling our stories. Part of why we are so targeted is that we've not had the proper investment in our communities’ storytelling. We're never going to outspend the opposition, but we can outmaneuver them through our storytelling and narrative power.

What is your biggest hope for philanthropy moving forward?

Let’s move away from the competitiveness of philanthropic resources only going to a select few and start collectively looking at sharing those resources. Whether you're investing in Transgender Law Center or another trans organization, how are you part of a broader ethos of changemakers to say we're creating a world we deserve? Not just constantly on the defensive, but really taking that time to do the deep visioning and power-building that we're so capable of but oftentimes don't get the opportunity to do because it's like always on to the next thing.

If we can get to a place where we are resourcing the grassroots instead of always prioritizing the grass tops. If we can understand that long-term investment isn't going to be a strategy that can be written down on paper and put into reports, but it's more sort of a long-term intervention where we'll see that play out in a myriad of ways. Look at Transgender Law Center’s growth arc in the last 20 years; every organization should be able to be in a place where Transgender Law Center is, to incrementally grow their resources, infrastructure, mission, vision and values to meet this moment.

Michelle Dominguez (they/them/elle) is a Queer and Nonbinary professional born to Colombian immigrants on Tongva Land, known post-colonization as Los Angeles. After a decade-long career in higher education student affairs, they switched to the nonprofit and philanthropy sector in 2021. What brings Michelle joy? Quality time with loved ones, mindfulness, dark chocolate, and Disney magic.