We caught up with the brilliant and insightful Faith Holiday AND Westley Holiday a few weeks ago and have shared our conversation below.
Faith Holiday AND Westley Holiday, thanks for taking the time to share your stories with us today Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?
ANSWER FROM WESTLEY TODD HOLIDAY:
Well, you know, our father, Westley Sr., didn’t know anything about starting a nonprofit. I think at that time, almost 25 years ago, the nonprofit sector looked very different. People were just trying to give back, you know. They were just trying to do something good. He and our mother, Judy Holiday, who did the business side of things, knew that a regular corporation wasn’t going to be it right way to get grant funding or to get corporate support, the nonprofit seemed to be the best way to go, so they just had an idea again. They were both the first in their families to go to college. Then they helped their brothers, sisters, cousins, and nieces go to college. I believe they just wanted to replicate that, for as many people as they could, right?
I don’t think they realized how big Holiday HOOPS & ARTS would be. I know the way that Faith and I flow, my Co CEO, we just kind of see what’s out there. We say, oh, there’s a new program. Faith has traveled to see tournaments all the time, and people are creating new basketball leagues. So, just last year, we decided to launch our own HOOPS Basketball Academy summer league. From marketing to website to social media to getting teams to sign up, gracefully it was very successful. I know last year, I wanted to do our first-ever Community Skills and Health event. So, I went out there and got a grant from the Allstate Foundation. Our team brought in vendors to talk about healthy eating. People talked about what it’s like to get good sleep and nutrition. We had a dance off, led by me and Faith, LOL. We talked about sports and the concentration that it takes to be a successful athlete. My sister, Faith, knows the business of basketball and has a great network in Orlando. Being that I know theater, I’m an experienced project manager and used to producing events, we had great support from our amazing Board, Advisory Council, parents, and volunteers. Last month, we completed a soft launch of our ARTS program by sponsoring a Debutante Cotillion cultural event for young ladies seeking college scholarships. We just walk through the steps, use our creativity, our network, and we know what we do know, or don’t know, to get it done. So we are being supported by a great team – an assistant, a coordinator, a manager, and interns on staff. Plus, a wonderful community of volunteer coaches, team parents, and many partners who want to help us.
Faith Holiday AND Westley Holiday, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
ANSWER FROM FAITH:
My name is Faith Holiday. I was born in West Palm Beach, Florida, and grew up immersed in athletics and community service thanks to my parents and extended family. My earliest memories involve traveling with them to tournaments and championships—that’s where my passion for coaching and youth development began. Today, I’m proud to carry on their legacy as Co-CEO of Holiday HOOPS & ARTS, a nonprofit I’ve led for over a decade.
I’ve coached basketball at every level—from Freshman to Varsity and even college teams in Georgia—and mentored over 100 young athletes along the way. I’ve also worked in the school system supporting students with special needs and volunteered with the NBA’s Orlando Junior Magic program. I hold a Bachelor of Science in Sports Marketing and Media from Full Sail University.
Beyond the court, I’m a music lover and rap artist, and I bring that creative energy to my “defense of mind” coaching style, which focuses on trust, communication, and skill-building. I coined our program’s motto, “One team, one dream,” because that’s exactly what we strive to be—united and purpose-driven.
ANSWER FROM WESTLEY TODD: Hi, I’m Westley Todd Holiday, Co-CEO of Holiday HOOPS & ARTS, I’ve always been the artist in a family of athletes—singing, dancing, and acting from a young age. After earning my degree in musical theater, I performed professionally in NYC, regional theater, and on cruise ships. Somewhere along the way, I discovered a love for project management and went back to school for a master’s in nonprofit management.
My work has taken me through hospitals, universities, and nonprofits of all kinds. But what drives me most is creating impact through the arts and education. Holiday Hoops & Arts, founded by my parents, exists to show underserved families that sports and the arts can be powerful tools for growth, connection, and discipline.
We know mentorship and positive reinforcement can change lives. Whether it’s learning how to pivot on the court or improvise on stage, these outlets build resilience, reduce stress, and improve focus. At the heart of it all is community. Not every kid has the same support system at home—but through our programs, they find one.
I’m proud that we’ve built a place where young people can thrive—mind, body, and soul. Because for us, it’s always been more than basketball. It’s about belonging. It’s about “One team, one dream.”
Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
ANSWER FROM WESTLEY TODD:
It’s funny. What I will share is, you know, I’ve worked with a lot of boards. Not only did I study board management when I got my degree in Nonprofit Management, but I was the board president of a nonprofit, which I won’t say by name. I also worked professionally with boards in my day job. There was one time we were producing an event. It was the 25th season anniversary, the first time Gala, and there were a lot of high stakes. I think that we were pushing to get through it. I was using my project management, my task-oriented mind, to get it done, and it got done. But it was very stressful, and I think a lot of strange relationships. We certainly raised a lot of money, but at the expense of infighting and interpersonal issues. What I realized is that you can be the best project manager in the world. But if you lose sight of the goals and the people behind the project or the event, you’ve lost big time. As a leader, it could be pretty humbling to recognize that. So here we are now with Holiday HOOPS & ARTS, and I’m the Co-CEO, and many years later, I take that important lesson to heart. I’m excited to see Holiday HOOPS & ARTS go into its 25th season anniversary with a community celebration, with a fun and unique gala in 2026. And this time, I’m going to do it with and for the people in mind. Because at the end of the day, it’s about people helping people. That means more to me than hitting the goals and achieving all of this money and accolades. Because again, we are here for the people. We’re here to create better communities and a vision for the future for generations to come.
Can you tell us about a time you’ve had to pivot?
ANSWER FROM FAITH:
Funny thing is, it all started with playing video games and having kids come around the neighborhood to play with us when we were in college. A kid named Xavien Smith mentioned to me that his grandfather was a part of a basketball club called the FBVA. And as a young college student doing the same thing over and over, I just started to take over my parents’ nonprofit, Holiday HOOPS & ARTS, and start coaching basketball. Even though everyone hasn’t gone off to play college basketball or become professional athletes, these kids have earned their rings to be great citizens and leaders for generations to come. As I started coaching, I developed a love and a passion for the game, which drew me into wanting to coach college basketball and the NBA. Once my mind was made up, I decided to go back to school and earn a Bachelor’s degree and Sports Marketing and Media. This helped me to develop relationships at the high school level and gave me the experience needed to further my career. On the HOOPS side of the organization, I provide skill development through training and knowledge of the game through coaching. On the SKILLS and HEALTH side, I work on self-esteem and critical thinking as the kids navigate through life. We have traveled to six states, won multitudes of awards and championships, seen kids go to college/get sports deals, and served nearly 2,000 people in 24 years of our program. Yet I’m most proud of the opportunities that Holiday HOOPS & ARTS has provided for not only me, but for the community, families, and the kids in the program. Our vision is about building a legacy and something deep for generations to come. That’s deep indeed and makes us feel so good.
Contact Info:
- Website: https://www.holidayhoops.org/
- Instagram: https://www.instagram.com/holidayhoopsbasketball/
- Facebook: https://www.facebook.com/HolidayHoopsAndArt
- Linkedin: https://www.linkedin.com/company/holiday-hoops-arts/
- Twitter: https://x.com/HolidayHoopsBB
- Youtube: https://www.youtube.com/@holidayhoops5024
- Other: Tiktok @hoopsandarts
