D Magazine interview by Ben Swanger

January 30. 2026

The mother-daughter duo connects two of Dallas’ most influential nonprofits at a pivotal moment for arts, workforce development, and women’s advocacy.

Today, Jan. 30, marks Lily Weiss’ last day as executive director of the Dallas Arts District, closing out a decade-long tenure. At the same time, her daughter, Erin Weiss Chupka, is stepping into a new chapter of her own. The newly named executive director of Girls Inc. of Metropolitan Dallas is just a month into leading a growth plan for the nonprofit.

For the mother-daughter duo, the moment feels less like a passing of the baton and more like a continuation of a shared mission—one rooted in creating opportunities for all.

In her previous role as Girls Inc.’s senior vice president of programs and services, Chupka helped expand the organization’s reach by more than 300 percent and secured more than $3 million in corporate, foundation, and government funding.

During Weiss’ 10-year stint, the Dallas Arts District was named the No. 1 arts district in the nation by USA Today in 2024 and 2025. She oversaw its expansion from 68 acres to 118, helped secure $75.2 million for arts and culture in the city’s 2024 bond program, and guided the district into becoming a measurable economic driver, generating $342 million in annual impact and $62 million in tax revenue.

Jill Magnuson, the district’s former board chair and former director of external affairs at the Nasher Sculpture Center, will serve as interim executive director while a national search begins for a permanent successor.

As they navigate transitions—one into retirement and the other into growth mode—D CEO sat down with Weiss and Chupka to talk about multigenerational leadership, building teams and institutions that last, and their shared commitment to championing women and the arts across Dallas.

D CEO: Lily, let’s start with you. When you look back on your tenure, what are you most proud of?

WEISS: “When people ask me what has stood out about these 10 years, I don’t think about specific achievements. I think about the people. I couldn’t have asked for better inspiration from leaders in the field. And I’m not talking just about the arts. We’re a neighborhood, so I’m really talking about all aspects of this neighborhood. It is truly mixed-use, especially when you have multimillion-dollar buildings next to a public school, and five historic buildings—with three of them being historic churches. So it’s a huge mix, and I’m grateful for that.”

D CEO: Erin, you’re at a completely different point in your career. What are you most looking forward to?

CHUPKA: “I’m in an exciting time of growth and transition. So I had the privilege of serving as the senior VP of programs at Girls Inc. of Metropolitan Dallas for the last eight years, and have recently been promoted into this role in an exciting time. And so it has been really fun to hire my replacement and build upon the great work that we’ve done, but shifting into getting to be more external-facing and engage with our community in a different capacity is great.”

D CEO: What lessons have you taken from your mom into your new role?

CHUPKA: “As I’ve reflected on why I’m so passionate about the Girls Inc. mission and what we do—and thinking about how talent is equally distributed but opportunity is not—I always come back to my mom. I’ve had a front-row seat to her all these years at Booker T. Washington [where she formerly served as artistic director]—and I mean the literal front row. If there was a dance concert, I was there in the front row. But seeing over and over, there would be students in the school who didn’t have access to resources for a lifetime of top-notch training. But then before you know it, they’re at Juilliard and performing globally in renowned companies. I believe so passionately that if we provide girls who don’t have access to that same kind of support, they can thrive, dream big, and be wildly successful.

“Another lesson I’ve learned is my mom is not afraid to advocate for what she believes is right. She’s not afraid to be a voice for people when they can’t find their own. People describe her as a firecracker. When it’s time to challenge a decision or make ‘good trouble,’ she does so in a way that’s not abrasive, because she has relationships with people and she’s respected and passionate. It ensures that she’s heard and is able to be that voice for people who can’t find their voice.”

D CEO: You both are advocates for women and underserved communities. What does Dallas do right and what does it do wrong when it comes to supporting and uplifting these groups?

WEISS: “There’s this assumption that the Arts District is only for the wealthy, that the arts are only for the wealthy, and that’s such a misnomer. Yes, the buildings are architecturally stunning, and it’s a neighborhood rich in real estate, but it’s also rich in people. What I know to be true is that every cultural organization has deep partnerships in underserved communities. They’re not always schools—sometimes they’re entire neighborhoods.

“That was always my goal: to make sure that message reached our community. Yes, we offer world-class programming, but our work goes far beyond that. Our symphony provides private lessons for underserved students. Erykah Badu bought instruments for those students. Those are the stories people need to hear about Dallas.

“At the same time, we know the arts require funding, and we work very hard with City Council and our local government to advocate for that support. We’ll take our share of hits, as long as they’re equitable. What we won’t accept is the idea that the arts are expendable.

“So it’s about having a voice, but also about understanding what the community truly needs. I also believe we’re becoming a much more international city. We’ll see just how much in a few months, when the World Cup arrives and we welcome hundreds of thousands of visitors a day. I’m excited about that. I’m a little frightened, too. But the idea that all of us are coming together to make it a great experience—that’s what matters most.”

CHUPKA: “When I look at it through the lens of Girls Inc., one of the most encouraging things over the last few years has been how the Dallas community has embraced the importance of workforce development. At Girls Inc., we place high school girls in paid internships and job-shadowing experiences, and opportunities like that just weren’t common outside of something like a mayor’s internship program. Workforce development has traditionally been structured around college students.

“But what we see every day is that if young people aren’t exposed to careers early, they don’t even know those paths exist. They don’t have the context to dream about them or pursue them. So we have to start earlier. We’ve seen great success with partners ranging from large corporations to small businesses and community organizations who are willing to say, ‘That makes sense—let me help place these young women.’ It’s been wildly impactful for the work we do.

“One area where I think there’s room for improvement is the funding landscape. As nonprofit leaders, we operate with a lot of constraints around resources. We want to collaborate and partner and maximize our impact, but we don’t always know what other organizations are working on. Funders and corporate partners sometimes have better visibility because they’re talking to everyone individually, while we often don’t have the time or space to gather and share that information. Corporations may be investing in specific parts of the community and have a clear view of who’s focused where and doing what. I’d love to see them play more of a connector role so we can collaborate more intentionally and leverage our collective resources for the greatest impact in Dallas.”

D CEO: Different generations sometimes do things in different ways. How have you seen your generational differences manifest in the way you two lead?

WEISS: “I’m from Filipino culture, where the mother is the matriarch of the family. We were raised in very strict environments. And when I say strict, it was with love, and we always understood why we were doing what we did. You also have to remember my father was in the Army, so there were high standards we had to live up to in order to match what he was being judged on.

“What Erin has been exposed to is this idea of women’s liberation before itThe mother-daughter duo connects two of Dallas’ most influential nonprofits at a pivotal moment for arts, workforce development, and women’s advocacy was even a thought or a seed of an idea. What she saw was a family of women who were strong and opinionated, who could debate and still come to some kind of compromise.

“I knew it was a match made in heaven when she went to work for Girls Inc.”

CHUPKA: “For better or worse, I’m a clone of my mother in some ways. She instilled an exceptional work ethic, this incredible stamina, and a relentless pursuit of excellence.

“There are some things I’ve learned, though, that I’m trying to do differently, and that’s the importance of balance. Trying to find balance is really hard, especially when you add motherhood and everything that comes with building a career. When I was growing up, we didn’t have words like self-care. Those weren’t concepts we were taught. We were taught to tough it out, push through, and just get it done. And I’m grateful for that persistence.

“But I also appreciate what I’m learning from other generations about the importance of the idea that you can’t pour from an empty cup. You have to be just as intentional about rest and rejuvenation as you are about your work, so you can show up better for your community.”

D CEO: Erin, your mom is ending a chapter. But you’re beginning one. Tell me about your goals this year.

CHUPKA: “We’re in year one of a really exciting eight-year growth plan. In my former role at Girls Inc., I helped work with strategy consultants to better understand the need in Dallas and to build this growth strategy and plan. So it feels incredibly meaningful to have the torch passed to me and to step into this new leadership role to guide the growth we worked so hard to design.

“What I’m most excited about is building the team that will go on that journey with us. I spent the first six months or so hiring my replacement, filling key roles, and laying a strong foundation for the continuation of our culture and how we’ll scale our impact—especially in terms of the number of girls we aim to serve.”

D CEO: And, finally, Lily, what does retirement hold for you?

WEISS: “I won’t have a commute every day, and that is a luxury. During this time, I’m transitioning into a volunteer role on my own schedule to help make sure this transition goes smoothly. It’s really the only reason I felt comfortable retiring, so I’m grateful for that. But for it to be successful, I need to stay available and pay attention to all the ins and outs. Meetings are one thing, but it’s all the details you don’t always think about—payroll, partnerships, who your part-time staff are.

“Folks have asked what I’m going to do on my first day of retirement. I’m not sure, but I can tell you what I’m not going to do. I’m not going to open up my laptop. I’m not going to answer an email. And I’m definitely not going to look at an invitation for a calendar invite.”