Alright – so today we’ve got the honor of introducing you to Rondal Richardson. We think you’ll enjoy our conversation, we’ve shared it below.

Rondal, thanks for taking the time to share your stories with us today We’d love to hear about a time you helped a customer really get an amazing result through their work with you.

I really am just a rather ordinary fella that extraordinary things have happened to. Some of the magic in this lifetime was a bit organic while quite a lot of it was reconciled with pure grit and tenacity. With all of the hats that I’ve worn and collaborations I’ve been lucky to be a part of in my professional career, there is an equitable and meaningful dose of transcendence in the work of serving others. Something that made the moments of brilliance even more profound. I had the remarkably great fortune early in my career to get to cheer on Garth Brooks as he navigated unprecedented superstardom with humility and kindness. No one was a stranger to Garth. He manifested community in such a remarkable way and allowed others like me to tagalong for some of it. From the earliest days in 1990 as I quietly watched every fan interact with him in the whispers of the night while I sold 8×10 photos by his side, he taught me how to be a blessing to and for others. He never stopped. He never cut the line off. Somehow magically, I was a small part of his gargantuan twenty-three hour autograph signing at Fan Fair back in 1995. It transcended time and space in the most amazing ways. That whole day was quite otherworldly. I was always honored to get to be a student in these classroom manifestations of one of the greatest careers in music. Then- who would’ve thought- a country icon for the ages like Wynonna would be one of the faces of the movie launch of the original “Lilo and Stitch” in 2002? It blasted us onto an extraterrestrial adventure like no other. Wynonna was the queen of taking chances. And that little phenomenon of a movie is still lifting our hearts and spirits some twenty-three years later- with a 2025 summer smash live-action update of one of the sweetest film franchises of all time. When I worked at Vanderbilt, a common question I had from my peers in the music business with whom I was manifesting relationships and partnerships for the Medical Center and the University at the time was “how in the world are you going to make this place warm and fuzzy?” No problem I thought. The transformational leadership of Vanderbilt at the time knew exactly how to conspire for good. I enjoyed building early relationships with the Nashville Predators and the Ryan Seacrest Foundation for this beloved place. The gold standard of teams at Vanderbilt in this era was not afraid to take big swings for the fence, and I was honored to have a seat at the table. To follow, being a part of the leadership team at Onsite is an experience for which I have always felt grateful. I appreciated the creative ways everyone worked as a team to build trust and hospitality for our clients, many of whom were from the music and entertainment business and often were the first to give love towards others but all-the-while neglected to store away some of their extra love for the rainy seasons. There is no one better at taking care of others than the crew at Onsite- shine on friends. Now with my work at the Community Foundation of Middle Tennessee, the home of customizable philanthropy, and the place where I have worked longer than at any other place in my career and where I get to be part of something bigger than any single person or singular movement, I sit in awe of what it means to change the world. The Foundation exists at the magical intersection of geography and geometry in caring for others by affording so many donors and friends the once-in-a-life opportunity to build lasting legacy and specificity with their philanthropic dreams. Sometimes you meet someone at a really tough part of their journey, and nothing is more meaningful than giving them options to change and impact the world. In 2025, we now have over 125 partners from the world of entertainment creating a seismic and revolutionary impact on the world of philanthropy. No one I know is doing what we are doing and in some ways it feels like I’m a kid back in 1986 navigating and fronteiring new opportunities for cosmic world order for the non-profit partners we get to support. One of my most cherished ride-or-die partners at CFMT is Trisha Yearwood. Four years ago, she came to us and said that she wanted to revolutionize the way we provided philanthropic support for animal communities around the country and in our own backyard. As a result of her remarkable belief in others and in beloved support for our furry friends, we have navigated unique charitable support for animal nonprofits and pet shelters in all 50 states in these first couple of years of building her initiative- Dottie’s Yard. Her remarkable ability to tell a story and to amplify goodwill for our animal friends who don’t get a voice for themselves has transformed the way we talk about customer service at our foundation. Our music community foundation partners have such a remarkable way to share stories and to turn melodies into moments. Having been a small part of this collaborative partnership with Trisha, Mandy, Cheryl and Callie reminds me of how we can best show up for others. We listen and learn. We take chances. We try new things to get to solution. And Trisha makes everyone feel like they can go twenty more rounds. She’s in the hall-of-fame category of doers and believers and encouragers. Her music talent is for the ages, without a doubt, but her heart to support animals and those who need it the most has literally changed my life. There is a lot of work left to do- Trisha and our entertainment partners have shown up in historic ways over the past two years to support those affected by natural disasters whose worlds turned in on them in Florida, Western North Carolina, Maui, Los Angeles and Eastern Kentucky. These CFMT partners are and forever will be on the “Mt. Rushmore of Philanthropy” in my heart. Customer service and hospitality for others is running in for support- not away. And I’m happy to help navigate this for these cherished artisans who are changing the conversation around entertainment philanthropy. What’s meant to be will always find a way.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Most of my friends know the legend and lore of this part of my story. When I was a rising senior at Battle Ground Academy in Franklin, Tennessee, in 1986, our beloved principal Dr. Lucas Boyd stood up at our student assembly one day and mentioned that he had “the summer job to end all summer jobs.” I was a 17-year-old boy who was barely paying attention, my head was almost always in the clouds. Thinking back to that moment, I hardly remember the specifics of the job, but I do remember experiencing a moment that I had never really felt before: the kind of moment that you know has the power to change the trajectory of your life forever. Basically, the job was selling merchandise out on the road in the ravenous rebirth of country music known to me as the “great traveling show of 1986.” The Judds, Ricky Skaggs, Alabama, Reba McEntire, George Strait, Randy Travis and countless other heroes of mine were revolutionizing the music business and connecting to a world audience in ways unseen prior to this era. It was traditional in form and style, but nothing could touch the power it had on the audience. It was all about the connection to others- to build community through the art. And I wanted to be a part of that. As a non-musician, it was the greatest of scenarios for me. You don’t need to speak the language to understand the feeling. Little did I know that all the best versions of my dreams were conspiring to make this work out for me. I remember asking my parents if I could even entertain this scenario as a seventeen-year-old, and my mom, with a brave lump in her throat, said that I was crazy if I didn’t consider being a part of this in some way. I was a good kid, not a troublemaker. At the time, I was earnest and followed the rules and was always willing to show up and learn every single thing I could. I wanted to understand what I didn’t understand. I honestly think I got the job because I was the only one whose parents would let them do it at the time and also because I was tall and somehow that made me look older than my very innocent and naive seventeen years. What I remember most about that first summer was how much of the music was built in and around the connection to the fans. Any form of entertainment is grounded in community- whether it be music or sports or film or literary. A college buddy of mine asked me recently, did I ever in my wildest dreams imagine that I would still be doing this 40 years later. The question took my breath away. I think my family always knew what I didn’t know about myself in those early days- that I was built for this. For the first 10 years, I kept saying that I wanted to learn as much as possible and soak up everything. I was trying to be an excellent student who wanted to be taught all of the nuances of the business. Some of the learnings came naturally- but the part about the work that allowed me to get to take care of others was the tune my heart was always plugged into at the time. I thought I would pack my bags and head to law school at some point. Unfortunately for me but for no other soul on the planet, law school never winked back at me. I think I was somehow destined to be a road scholar. Learning trends, understanding how to take care of people, figuring out how to build a brand or how to ignite entrepreneurialism in others were the master classes I wanted to be a part of in that era. I wanted to give up a thousand different times- it was hard to travel so much. But there was so much to learn then and now there is so much to teach. Next year in 2026, somehow by remarkable faith and happenstance, I will have had the blessed fortune to celebrate forty years of being an ancillary part of this music and entertainment ecosystem. When I even think about that number, I feel like the world around me is finally taking a deep breath or maybe that’s just me, finally exhaling. All the best pathways are waiting for us if we just stop and smell the roses once in a while. I just raised my hand that fateful day in 1986 and some four decades later I realized that I never looked back. These mentors and friends who became an enormous part of my story understood complex relationships and hospitality and how to make others a key part of something bigger than we ever experience individually. I was restless in college and did everything that I could to navigate and reinforce my participation in this industry as my life’s North Star. I studied the Billboard Charts in the late 80’s with my college roommate. I laugh about that now, only because the universe was already conspiring to pull me into this atmosphere in some way, shape or form. It had me at hello! The music and entertainment business is grounded in the notion that when we stand together, it’s our finest hour. None of the success of the people that I’ve watched and supported in these past four decades happened by accident. There were no overnight successes that I can ever recall. “Success” was rewarded by ingenuity and perseverance and the belief that we could move mountains if we move them together. I think one of the things that would be most surprising to others about this industry is that there are not millions and millions of people making these decisions around how to deliver music to the masses. There are often limited teams with limited resources but armed with unimaginable and limit-free curiosity and creativity which had no bounds and which created some of these great movements in music. I’m a sixth generation Middle Tennessean, and I marvel at the way my community has been amplified for good. The robust growth of Nashville in the last several decades did not happen by accident. I think about the city when it first landed three interstate systems into our little big town and how it divided historic neighborhoods but ended up bringing weary travelers and young dreamers to our magical shining village. And later when that first transcontinental flight to London was awarded to Nashville, all of which paved the way for some other tremendous opportunities for our music town of misfits and dream-chasers. The Titans moved here and then the Nashville Predators came, and suddenly the world was watching our little village of hope and transformation. We were the personification of the little engine who could. None of those things ever happened in a vacuum. It was built, brick by brick by brick, by the resilient spirit that is so unique to the Middle Tennessee community. It felt like then, and now, that everyone had a seat at the table to make this community shine even more brightly and beautifully. That’s the magic of this industry and of the arts in this town from which so much timeless music has been made and created here. And now we are experiencing a new world order so that all types of art will continue to be made and manifested here. For the little seventeen-year-old in me who never imagined still getting to be a small part of this musical movement, it feels like every ride at Disney World is going upside down. All of the joy that comes from feeling like this giant dream of being a helper and supporter in the trenches with others, not only came true but became a lightning rod in the support of encouraging and inspiring others. My hope is that by what has been built and by what is to come, that others will join us and breathe even more stardust into this beautiful anecdote of authenticity and collaboration and generosity and trust and transform us to even greater heights! Never give up, friends.

Can you tell us about a time you’ve had to pivot?

I call it the great pivot of 2007. Two years prior to my whole world order getting disrupted for good, I had the esteemed life pleasure of getting to help raise money with Wynonna for Habitat for Humanity in 2005 as a result of Hurricane Katrina. My parents had always been community leaders and activists, so I realized that it was no surprise that my DNA was subsequently activated in its deepest components in the service to and for others in those early days of the great pivot. When Habitat called, we jumped in. All in. And a light came on in me that has never been extinguished. At that time, it felt like a memory I’d even forgotten that I had. We committed a lot that year, a lot of bandwidth and family time to spread the message of hope and healing for our friends and neighbors in New Orleans. That quickly manifested into one of my happiest years in the business in 2006 and a day on Capitol Hill with Wynonna that I will never forget. We rode the Senate train with Senator John McCain and spent sacred time with then-Majority Leader Bill Frist in the support of YouthAids/Population Services International. We were part of raising one million dollars for that singular event. At a dinner that night, Wynonna remarked that she had seen a different gear for me on that day. A proverbial spring in my step if you will. She said, “you really do a great job of taking care of everyone but when we have these activism days in service to others, that’s when you really come alive.” She said, “this kind of service is something I think you should consider as a career pivot.” I remarked flippantly, “yeah, when I win the lottery.” She then blessed me with the truest and kindest sweetness of my life, “oh friend, you won the life lottery.” As fate would have it, she was quite right. I launched out on my own in 2007 and connected with every nonprofit and charity across the country that I loved and cherished. I sat across the table with every thought leader and charity team and asked, “What can we do together to make the world an even better place? What do you need that you cannot do alone?” I crisscrossed the country more times in the next three years than I had in any of my years in promotion and support of the music artists I was promoting. I had the door shut in my face a gazillion times and yet had some of the most amazing things that could ever even happen to a young philanthropist, which most people wait an entire lifetime to experience. I was a lucky chap, indeed. About four years into my career as a burgeoning philanthropist, an important leader and challenger who I deeply cherished and respected said, “I believe that you are going to be successful because I believe in you. But I also need to say that I don’t believe the entertainment industry is philanthropic.” Challenge accepted! As a result of this amazing pivot in 2007 and the remarkable entertainment community with whom I get to work, I’ve been a part of over $350 million being raised for charitable support in these last two decades. I’m merely citing that as data to provide a “call and response” to my friend’s theory that the music and sports and arts communities were not philanthropic. It’s not so much that I wished for her to be wrong but rather how I knew in my bones that this type of philanthropy with entertainment partners was right. In this gigantic pivot, some of the greatest professional series of accomplishments for the greater good of my career helped to change our community. What a blessing it is to carry the torch for those who are weary and cannot do so for themselves. We all need a little help now and again. We all need a boost or a lift, and it has been the honor of my lifetime to be able to jump right in to connect artists and actors and athletes and musicians to noble causes around the planet. I’m just one person, but I stand on the shoulders of so very many of those who came before me and who believed in community and that we could do anything if we set our hearts to the compass of helping others. I am a charter member of those brave souls who believe in the resilience and magnanimous power of community. And now, I get to teach others these same formulas that have worked in support of people who want to change the world together. Never has the world needed philanthropy and activists more than today! Everybody gets the chance to be a part of this and can be a part of this and will be a part of this in one form or another. I’m not the smartest guy, but I’m resilient and I try hard. I always look for the work-around when the world shuts the doors in our faces. I have a beautiful personal board of directors who challenge me to think towards the next twenty years as I wistfully reflect upon the last twenty. In some ways, I was always hard-wired to believe that we can never rest on what has happened but only on what good will happen. It all goes so fast- I’ve never taken for granted one single nanosecond or for all of the answered prayers. And I also know in my liver that we’re just getting started!

Can you share a story from your journey that illustrates your resilience?

The world view of community service is changing daily in 2025. I’ve spent a lot of time in the last year talking to and learning from students who are graduating and are coming into the workforce with so much heart and so much ambition. It feels like we are going to learn a lot from this generation. These resilient souls who were born into a post-911 world to evolving agendas and political regimes are surviving and thriving and have quite a lot to say. Might I also suggest that we have a lot of listening to do too, friends. As much as I feel like I have a lot to teach after four decades of service work with the world, I look even more forward to continuing to be a student with and for those transformational leaders who are to come. I can’t wait to think of the new and creative ways we are going to be able to lean in to help others in these next few years. It’s a critical time in the world. Resilience is often hard when talking about philanthropy today. People can be suspicious and judgmental. As a faithful follower of Ted Lasso- it just makes me want to be even more curious. A member of the Congressional Oversight Committee called me earlier this year to seek some advice about how we have been able to amplify philanthropy in the last four disasters they had studied: namely relief efforts for the Maui Fires in 2023, Hurricane Idalia in Florida in 2023, Western North Carolina flooding as a result of Hurricane Helene in 2024 and the Los Angeles fires in 2025. As a result of this particular Congressional member’s due diligence around disaster philanthropy and studying those four campaigns in specificity, he found that we were the only foundation to make grants to each of those relief efforts. That blew my soul wide open. Not because of anything in particular that we did- we were the mere conduit for such generosity. Our donors drive what they want to support. And I’m here for it! I’m here for sharing and for navigating the good for and with others. I have witnessed so many of my superheroes pulling the sword from the stone when called upon to help. It summons the greatest parts of our souls to activation when our friends and neighbors need us. When I think about philanthropy these days, it feels like this type of work is calling upon our great bravery as a society. Is this really all about justice? Injustice is often disguised as bad luck, and I don’t believe in that kind of world. When I started this tapestry of work over two decades ago, I remember hearing Bono say in an interview for the Live Aid concerts in 1985, a mere year before I jumped into this pool, “you wouldn’t need charity if the world was just?” I ruminate over that a lot when resources are limited and tensions are high. Yes, perhaps there is a new need for philanthropy AND justice. But I also believe that people truly at their core are compassionate and want to help their neighbors in the name of love. It takes all of us to amplify the total good we get to share in the world. No one rises alone. I cannot imagine a more meaningful navigation of community building and stewardship and hospitality and care for others than the new world order that we are creating together. It is going to be the blessing of our lifetime to get to make more possible through the power of philanthropy in new and brave ways.

Contact Info:

• Website: https://www.cfmt.org/donors/entertainment-philanthropy/
• Instagram: https://www.instagram.com/rockinrondal/#
• Facebook: https://facebook.com/rondal.richardson
• Linkedin: https://www.linkedin.com/in/rondalrichardson/
• Twitter: https://x.com/rockinrondal

Image Credits

Headshot Photo by Molly Lins