DALLAS — Picture this: 150 people crammed into a living room. A full band. Holiday energy spilling into every corner. And twin brothers realizing that what started as a simple gathering had outgrown the walls containing it.
That’s how The Maiden Foundation began—not with strategic plans and nonprofit paperwork, but with Terrence and Tim Maiden hosting friends who showed up with gifts instead of empty hands, creating community instead of just consuming holiday cheer.
Twenty years later, that living room overflow has become a Dallas institution that’s invested over $500,000 into communities, transformed how the city celebrates Christmas, and built a legacy that’s now being handed to the next generation.
Rolling Out sat down with Terrence Maiden—visionary real estate developer and co-founder of The Maiden Foundation—to talk about two decades of servant leadership, why the Winspear Opera House felt like a dream come true, and how twin brothers divide responsibilities when building something that matters.
When 150 People in Your Living Room Becomes a Problem
“Well, candidly, it started before the 20 years ago,” Terrence told Rolling Out. “I remember hosting Christmas holiday events at my home, and would just tell friends and family to come over—don’t come empty-handed, bring a gift. We sort of outgrew that space, because by the time we shifted to do Soulful Christmas, we were having like 150 folks in my living room, if you will, with the band.”
Read that again. A full band. In a living room. With 150 people.
That’s not a party. That’s a movement waiting for infrastructure.
The first official Soulful Christmas moved to Button’s restaurant in Dallas. “It was a phenomenal event,” Terrence recalled. “We had RC & The Gritz perform, and standing room only, and so it just sort of grew over the years.”
But the Winspear Opera House? That was the dream they didn’t dare say out loud.
“When we first started Soulful Christmas, our hope was to get it to the level where we were hosted in some sort of major venue,” Terrence explained. “We never anticipated that it would be the Winspear Opera House in Dallas. But when we were able to solidify that relationship with AT&T Performing Arts Center last year, it was almost like a dream come true.”
This December 19 at 8:00 PM, The Maiden Foundation presents its 17th Annual Soulful Christmas at the Winspear Opera House (2403 Flora St., Dallas, TX 75201), featuring multi-GRAMMY Award nominee KEM and Dallas’ own Brittany Holmes. But the real headline is 20 years of proving that when you build with purpose, the venues eventually match your vision.
How Twins Divide Empire-Building
Rolling Out asked the question everyone wonders about twin entrepreneurs: how do you split responsibilities without splitting impact?
“Well, for the most part, I try to set forth the strategy for our organization, and I’m a big relationship person,” Terrence explained. “I’m also heavily involved with securing some of our strategic partnerships.”
Tim brings the numbers. “Tim, because of his banking background, he’s all in the numbers, right?” Terrence said. “So he’s responsible for all of our really compliance stuff, and he’s instrumental in making sure that we keep tabs on our expenditures and making sure that we’re good stewards over the money that is entrusted with us when we’re putting on events of this caliber.”
Translation: Terrence dreams and connects. Tim counts and protects. Together, they’ve generated over $500,000 in community investment through signature programs including Elevate Male Leadership Academy, Gold Chair Leadership Series, RedBird Tomorrow Foundation, Soulful Christmas, and Soup for the Soul.
The Return on Investment That Actually Matters
When Rolling Out asked about tangible returns beyond the half-million dollars invested, Terrence didn’t hesitate.
“There are so many opportunities to point to that,” he said. “I think one that probably resonates with me the most is our Elevate Male Leadership Academy that we partnered with University of North Texas on.”
The program mentors young men toward college and meaningful careers. But Terrence measures success differently than most nonprofits.
“It’s so fulfilling to see the young men who have gone through our leadership program go off to college and secure really meaningful career paths for their lives, and they come back and express how that Elevate program really makes a difference,” Terrence shared. “At that point, you’re not only changing these young men’s lives, but then you’re setting them up to be good fathers, good husbands, and then also good community leaders. And so that ripple impact really speaks volumes to, sort of, the work that we’re doing, and the investments that we’re making, and how we believe, ultimately, we’re making a difference in the communities that we’re serving.”
That’s not just mentorship. That’s generational intervention.
Why KEM Made Sense for December 19
Rolling Out asked what Terrence looks for beyond vocal talent when selecting artists for Soulful Christmas. His answer revealed the foundation’s deeper understanding of what Dallas needs during the holidays.
“That’s a great question, and we are really meticulous about finding artists that really, what we think would not only appeal to a wider audience, but also will produce something and provide an experience that would be uplifting for the holiday season,” he explained.
Last year’s artist, Tye Tribbett, taught them something crucial about timing and need.
“What we discovered last year when we had Tye Tribbett is that the holiday season is difficult for a lot of families, and having the opportunity to get out and about and go to a concert that’s uplifting, and while you can also jam to some good holiday hits, it is really inspiring. It’s encouraging,” Terrence said. “I can’t tell you the number of people that went to the concert last year and reached out and just said, thank you, that was exactly what we needed this holiday season.”
That feedback loop—artists who understand the assignment, audiences who feel seen—is what separates Soulful Christmas from every other holiday concert cluttering your December calendar.
Where the Money Actually Goes
This year’s Soulful Christmas, presented by Truist Bank, benefits two organizations doing essential work year-round: Harmony Community Development Corporation (providing food and counseling resources to Southwest Dallas and Red Bird residents) and Austin Street Center (supporting individuals experiencing homelessness).
“We try to look at a variety of things when we’re selecting the nonprofits to support on an annual basis,” Terrence told Rolling Out. “One, we try to really vet out their impact and the social causes that they’re fighting. The other thing is we look at their leadership team and look at the history of their work.”
The selection process isn’t easy given Dallas’s nonprofit landscape. “It’s oftentimes very difficult to find just the right group, because there are so many organizations in Dallas-Fort Worth that’s doing incredible work,” he acknowledged. “But it gives us the bandwidth and the opportunity to give to so many different organizations.”
Last year, the foundation supported Oak Cliff and Behind Every Door. This year, Harmony and Austin Street. The strategy? Support multiple organizations doing hard work year in and year out across the city.
When Sponsors Become Partners
When Rolling Out asked how The Maiden Foundation ensures corporate partnerships feel authentic instead of transactional, Terrence revealed the pitch that works.
“Well, we also try to position this with our sponsors, that this is an opportunity for you to celebrate your team, celebrate the holiday season, and come out and do something that’s fun,” he said. “And that has resonated with a lot of our sponsors.”
But the real selling point is track record. “The other thing is, our sponsors has seen the work of the Maiden Foundation over the last couple of decades, and we built the level of confidence and trust with our partners, and they are happy to support the endeavors that we’re focused on, because they know that, they know where our heart is, and they’ve seen tangible results from our work.”
That’s not corporate social responsibility theater. That’s 20 years of receipts proving your mission matches your marketing.
The Next Generation Gets the Baton
Rolling Out asked the question that matters for any 20-year-old foundation: what does success look like for the next two decades?
“Well, a part of our strategic plan, now that we have successfully made it to our 20th year, is we’re focused on the next five years of putting together some sort of succession plan with our family,” Terrence revealed. “And our hopes is that we can ultimately pass on the baton to our children to carry the mantle into the next two decades of making an impact in the city.”
This isn’t theoretical. “We’re hopeful that Tim and I have laid a solid foundation for them to build off of and do even greater works. And so, we are being intentional in involving our kids in what we’re doing now, in hopes that they will continue the legacy of the work that we’ve done in the city.”
That intentionality—bringing the next generation into the work now, not after the founders retire—separates organizations that last from organizations that fade when their visionaries step back.
December 19: More Than a Concert
This year’s Soulful Christmas at the Winspear Opera House isn’t just the 17th annual concert or even a 20-year milestone celebration. It’s proof that when two brothers refuse to let their living room limit their vision, when they turn holiday overflow into sustained community investment, when they measure success in transformed lives instead of just dollars distributed—the venues eventually catch up to the mission.
Tickets and sponsorship opportunities are available at maidenfoundation.org. The evening promises KEM‘s Grammy-nominated vocals, Brittany Holmes’ Dallas hometown excellence, and proof that soul, spirit, and giving create traditions Dallas won’t let die.
Twenty years. $500,000 invested. Countless young men mentored into fatherhood and leadership. A foundation being handed to the next generation with intention and infrastructure intact.
From living room overflow to Winspear Opera House. From 150 people with gifts to a citywide movement that transforms how Dallas celebrates Christmas while serving communities that need it most.
That’s not just a foundation. That’s what happens when twins refuse to play small.
The 17th Annual Soulful Christmas takes place December 19 at 8:00 PM at Winspear Opera House. Visit maidenfoundation.org for tickets. Follow @maidenfoundation on social media.