Shelby Chestnut was appointed executive director of the Transgender Law Center, the largest trans-led organization advocating for a universe where everyone is free to define themselves and their future. Chestnut was the organization’s first director of legislation and programs in 2017.
Chestnut, who was born in Montana and raised in Minnesota, is one of the first Native transgender leaders to lead a national LGBTQ+ organization and the first to be the executive director of the Transgender Law Center. They have more than 20 years of experience promoting the advancement of LGBTQ+ communities of color and advocating for them. Chestnut and Antioch College have Bachelor of Arts degrees in communication and social studies, and The New School has a Master of Science in nonprofit management and public policy.
Chestnut is responsible for overseeing strategic campaigning, organizing, and movement-building initiatives that promote the rights of transgender and gender nonconforming people across the country. The Transgender Law Center’s legal victories set precedents in areas such as education, immigration, healthcare, employment, and prison issues.
Internet spoke with Chestnut about their background, work at the Transgender Law Center, and hopes for the future. Here are some excerpts from the discussion, edited for length and clarity.
What do you enjoy doing when you’re not at work?
I like to collect things, and I have a large footwear collection and record collection. I enjoy taking road trips and visiting places I love. I’m constantly planning what I may do next.
What aspects of your personal story do you incorporate into who you are now?
I grew up in the ’80s in Montana and went to high school in Minnesota. My father is African, and my mother’s family is Norwegian. Where you’re from is a significant part of your identity, grounding, and connection to the earth, in my opinion. Even when I spent a lot of time living in New York City in my 30s, I always acted like I lived there.
My approach is to know your neighbors, be kind to them, and help people out. It’s how I started organizing: getting to know people and developing my own perspective based on what other people are saying. Now, things are very professionalized, and indeed, that’s real and important. For me, talking with people directly about their needs and their effects is the most genuine thing to do, even though I’m from another place.
What did you grow up knowing about money?
I didn’t learn much. I was raised in a lower-working-class household. My mother worked hard to give me access to the things she knew would help me succeed because she was a single mom. A bit of a troubled child, I had learning disabilities, I was gay, trans, and bullied, but in hindsight, she did all the things right to grant me this, quote-unquote, “access to a better life.”
The first time I ever learned about money and what it can or can’t buy was in undergraduate and graduate programs in New York City after the 2008 financial crisis. People in graduate school were 22 years old, and their parents paid for it, and I was about 30, commuting an hour each way.
To be honest, I kind of knew nothing about money growing up, which I think is a real advantage in this day and age where success is heavily based on people’s access to success, success entry, or proximity to wealth. The impacts of capitalism are a big part of the issues I’ve organized around in my life. It’s complicated because, on one hand, you’re working to increase marginalized people’s access to financial success, and you’re also fighting those same systems that oppress people because of capitalism.
When did you first realize that philanthropy was a part of the work you are doing?
It was a bit of an accident. I was incredibly fortunate for much of my career to have interactions with progressive, social justice-focused philanthropy. When I was about 25 years old, I worked for an arts organization in New Mexico where we would hold these social dinners following major art shows. I can remember sitting next to this person for the entire night and spending the evening just chatting her up without knowing who she was. It turns out she was the leader of the city’s largest foundation and was responsible for many of the arts organizations. I was really good at understanding how much of philanthropy and funding are about building a relationship, and that is where I come from. I can talk with anyone, virtually!
What role do you think the Transgender Law Center’s philanthropy and fundraising play?
I believe that our relationship to philanthropy is one of mutual need and that we are also in a position where we can influence to support transgender and LGBTQ+ movements, and I believe this will change the course of history. Being the largest trans-led organization in the nation and probably the world, we’ve grown this large by doing really important work. We’re very grateful to our supporters, and yet, we have a responsibility to push philanthropy’s bigger picture to think about, “What’s your investment in trans life”?
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 believe that as a progressive movement, we must understand that our opponents 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! However, it is now if it took a year to complete it.
However, we also need to realize that this is a social progressive issue that we are dealing with and that this is not just a trans issue. 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 planned for the Transgender Law Center?
For what is likely going to be a very difficult year for many people in the nation, we have some exciting things planned. Through the development of a trans power framework, we are attempting to fortify our movements. Our Trans Agenda for Liberation narrative lab, our newest project launching this year, involves colleagues from across the nation working together to discuss how we approach this situation as a whole and chart a course forward.
We have some other things to discuss as of right now, but I believe it will be a good year. We’re going to rely on our community more than ever, and I hope that they rely on us to consider how to tackle the issues at hand because we’ve already discovered that our communities are resilient. If they are invested in and properly cared for, they are particularly resilient.
What modifications have you noticed throughout your career in the philanthropic sector?
There is more trans leadership than there is in any other country. Ten years ago, there wasn’t a trans organization in every state, and I can assure you that it still exists. 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.
A crucial component of 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. We’re targeted because we’ve not had the proper funding for the storytelling in our communities, which is one of the reasons we’re so targeted. We can outmaneuver the opposition through our storytelling and narrative ability, but we can never outspend them.
What do you see as your greatest chance for the future of philanthropy?
Let’s break away from the competitiveness of philanthropic resources that are only available to a select few and instead focus on how to share them all. How do you join a larger ethos of changemakers who claim to be making the world we deserve, whether you invest in Transgender Law Center or another trans organization? Not just being constantly defensive, but actually taking the time to do the deep visioning and power-building that we’re so good at but frequently don’t get the chance to do because it’s always on to the next thing.
If we can find a place where the grassroots are being resourced rather than always giving the grass tops priority. If we can see that a long-term investment is not going to be a strategy that can be recorded and put into writing, but rather a long-term intervention where it will manifest itself in a myriad of ways. Look at the 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. They left their decade-long involvement in student affairs for higher education in 2021, making the transition to the nonprofit and philanthropic sectors. What joys Michelle? Quality time with loved ones, mindfulness, dark chocolate, and Disney magic.
