Bounce back: Formerly homeless Charlottesville resident will speak in front of the UN

Gwen Cassady is a formerly homeless Charlottesville resident turned activist and entrepreneur. Photo: Eze Amos Gwen Cassady is a formerly homeless Charlottesville resident turned activist and entrepreneur. Photo: Eze Amos

Gwen Cassady has lived a lot more life than could fit into a half-page newspaper profile. She’s been homeless four times, and spent a period living out of an office on the Downtown Mall. She’s been to 64 countries, as well as a royal Saudi compound, earned two degrees from UVA, and is currently enrolled in a Harvard graduate program. Next week, she’ll speak about her experience with homelessness in front of the United Nations as part of the organization’s Civil Society Forum. 

Through all those twists and turns, Cassady’s entrepreneurial spirit hasn’t wavered. She’s got a studio now, a small room tucked in the side of a warehouse in Woolen Mills, jammed with boxes overflowing with fabrics and beads. She has a dozen projects in the works, everything from a “net-positive, off-grid, small-home community” in Greene County to a jewelry business that sends 100 percent of profits to victims of Boko Haram in Nigeria. Her latest endeavor is Eco Chic Boutique, a clothing shop and tailoring service that Cassady coordinates with local refugees. They sell jeans, bridesmaid dresses, and other custom-fit apparel.

She’s also become a tireless advocate for homelessness awareness in Charlottesville, where our housing crisis has exacerbated an already difficult situation. Cassady is working on three documentaries about homelessness, and will premiere one of them at the UN. We caught up with her ahead of her speech on February 13.


C-VILLE: What’s the movie about?

GC: We focus on the global pandemic of homelessness, but our primary focus is on Charlottesville. We interview a lot of really awesome people, amazing people who are currently homeless, people who are formerly homeless.


What support was most valuable to you during your periods of homelessness?

I found that in Charlottesville, when I had too much pride to ask my closest friends for help and assistance, my homeless friends always looked out for me. My 35th birthday, I will never forget…They were pooling all their money from food stamps and from SNAP benefits, which I was on too, just so I could have a nice steak dinner on my birthday. I remember exactly where we were standing, right outside the library.


How have you managed to survive in so many different environments?

I’ve always been able to blend in to any environment because I’ve always treated everyone the same. 


You’ve been knocked down plenty of times, but you always get back up. Where does that resilience come from?

My daily driving forces are my friends who are currently homeless. Like Ricky on the Downtown Mall. Chris, in D.C., who was lit on fire by rich white kids. Understanding the systemic issues, I just want to make a difference.


What can we as individuals do to help?

My whole speech [at the UN] is about how the kindness of strangers reinstated my faith in humanity when I was homeless here on the streets of Charlottesville…You offer random acts of kindness. You do what you can do.


How does it feel to be speaking at the UN, after all you’ve been through?

It’s surreal beyond words. I still can’t wrap my head around it. I will never be able to, fully, even while I’m speaking.


Gwen Cassady, in brief

Education: UVA economics BA ’97, UVA education MA ’14, Harvard sustainability masters in progress

If you could pass any law what would it be: Removing the statute of limitations on sexual assault.

Priority for change in Charlottesville: Building more affordable housing.

Meaningful quotation: “The poverty of being unwanted, unloved, and uncared for is the greatest poverty of all.” —Mother Teresa


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