We caught up with the brilliant and insightful Reagan a few weeks ago and have shared our conversation below.

Reagan, thanks for taking the time to share your stories with us today Let’s jump back to the first dollar you earned as a creative? What can you share with us about how it happened?

Technically, the first dollar I ever earned from performing music wasn’t a dollar–it was a meal. In high school, I started playing at a local restaurant in Landrum, SC called Stone Soup once or twice a month in exchange for dinner. The restaurant is a very intimate environment since the building was once a single family home, so at first I was surprised that they wanted live music. Then they showed me where to set up–not on the patio, but inside what was essentially the lobby / waiting area just inside the front door. I sat down in a chair and plugged my small Fishman acoustic amp into the wall outlet thinking it would be an interesting night. But it was the first time that I ever felt like a legitimate performer. Even though it was a strange gig (and would remain so for my entire tenure there), I was being given something of value in exchange for my services as a performing artist. That was an amazing feeling! Needless to say, those meals tasted great; not just because that restaurant serves excellent food, but because the meals tasted of hundreds of hours of practice and a hard day’s work. Towards the end of my time performing there, I struck a deal with my dad: he would come watch me play, eat the meal I earned, and pay me what the meal would’ve cost. So I guess that was really my first dollar earned!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I was born and raised in Spartanburg, SC. I started playing guitar when I was 12 years old and never looked back. I played a lot of what I now call “small-time” gigs throughout high school and college. Not until the summer of 2021 did I launch my official music business: Reagan Leonard Music. In that first year, I really didn’t have a clear sense of where I wanted the business to go. I just knew I wanted to make a little bit of money doing what I love to do. As such, I played at any bar/restaurant/etc. who would pay me to play. My first 6 months were not marked by much success and I certainly was not raking in much money. But by the end of 2021, I played my first private event and that changed everything for me. I learned that not only do private events pay much better than bars and restaurants, but more importantly, they treat you better. They are actually excited that you’re there to perform because they handpicked you for their event. From then on, I’ve made it my mission to reward that good faith by giving my all to every private event that I perform for. I play all sorts of private events now from weddings and rehearsal dinners to birthday parties to corporate events to 60-year anniversary parties for couples in their eighties! What sets me apart from other musicians is my professionalism. My clients don’t get left on read. My clients don’t have to repeat their requests. My clients don’t have to worry about me being late. My clients don’t have to read long or confusing contracts. In short, my clients don’t have to worry about anything relating to music! When someone hires me, I am going to make sure that their event has top-tier live music that’s both classy and fun.

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

In February of 2023, I performed at a restaurant on Valentine’s Day. At this point, I was playing about 40% private events and 60% “public gigs” at bars and restaurants. I arrived 30 minutes before I was to start playing and the staff member who coordinated live music came over asking why I was just then showing up. I responded saying we agreed on 5:30pm, but he insisted I was late and that I needed to start playing ASAP. The night wore on and I was receiving less than average tips, which was especially frustrating given that the restaurant was packed for the holiday and I had voluntarily given up the ability to spend the evening with my wife. By the time I was driving home, I decided then and there that I would raise my minimum performance fee. This would effectively price me out of any bars/restaurants’ budgets and I was fine with that. Since then, I’ve performed almost exclusively for private events. While my overall number of events has decreased dramatically, my rates have increased, highlighting the value in private events. This has been the single most impactful decision I have made in my business and I don’t regret it for a second.

How can we best help foster a strong, supportive environment for artists and creatives?

I think the biggest thing people can do to support artists and creatives in their community is just to have something special at any event they put on. Whether it’s a work event, a personal one, or for an organization they’re a member of, hire someone who does something cool! It could be an electric violinist, a live painter, a balloon artist, an ice sculptor, a magician, or a singer-guitarist like myself. All of these things undoubtedly add a little special something to the event and make it so much more fun for the guests. And you’re supporting a local artist while doing all of that? So worth it!
Another way to support artists like me is just to talk about us. This really goes for all small businesses. When you see that person at the farmer’s market selling their gourmet cakes and they sell “tell your friends”, they mean it! They need you to tell others about them because their livelihood depends heavily on word of mouth. So just talk about artists that you know or have heard about in casual conversation with friends. You never know who could hear something that leads to a booking that would mean the world to a local creative.

Contact Info:

• Website: https://reaganleonardmusic.com/
• Instagram: https://www.instagram.com/reaganleonardmusic/
• Facebook: https://www.facebook.com/reaganleonardmusic/
• Linkedin: https://www.linkedin.com/in/reagan-leonard/
• Youtube: https://www.youtube.com/user/reagosie/videos

Image Credits

DiPietro Photography and Films
Carlee Hoopes