Trey Calloway & the power of persistence, creating momentum with your music

Q & A with Trey Calloway on Local Music Somewhere

Welcome back to rBeatz.com, and you’re tuned in to Local Music Somewhere, our flagship program dedicated to promoting independent artists and industry professionals who inspire and support them. I’m Terry Hudson, your host. I’m an author, speaker, and music industry coach. Today’s guest in the studio is Trey Calloway. This is going to be a fun conversation. Trey is a country music artist, a singer, a songwriter, and a multiple award winner, including the Josie Award, which is well-known in independent circles, and the Texas Music Association Award. I believe he may have one more accolade that I’m missing, but aside from all that, he’s just a great guy I’ve known since he was a teenager. Trey embodies perseverance in the music industry, showing how to forge ahead no matter the challenges. This will be a great lesson for those who might be tempted to give up on their dreams, especially in the music industry and the arts. Trey is the kind of person who, even if hit with 12 sledgehammers, will keep moving forward. He didn’t become this way overnight; his experiences shaped him. We’ll discuss that today. Welcome, Trey.

Hello, Terry. How are you today?

I’m good, man. How are you?

I’m doing fantastic. I’m glad to be here, buddy. I’m excited about this.

I’ve wanted to interview you for a while. Although we could have done this remotely, with you in Nashville and me here in Charlotte, North Carolina, our home base, I’ve known you since you were about 13 years old. I’ve watched your growth and everything you’re doing, and I really wanted to make it happen in the studio. You and I have been jumping through hoops to make this work, so it’s really cool to have you here. I appreciate you coming in.

Oh, it’s better in person. It’s great to be face-to-face.

Absolutely. Especially when you know the person and with a show that deals with independent artists, it’s important to understand that everything starts somewhere. They just have to get started. It doesn’t matter if they’re 12 or 35. I always say that your first attempt won’t be a masterpiece, but without that first attempt, you’ll never have a masterpiece.

Amen.

So, let’s start with your origins in music. How did you get started with music and the guitar?

Well, you and I both have our roots in the Pentecostal church. My dad was a Pentecostal evangelist when I was growing up.

That’s right. And a great one at that.

Thank you. I’ll be sure to tell him you said that. I started my music journey by singing at the different churches where he preached, often performing before he delivered his sermon. I was around six or seven years old when I began doing that and quickly caught the music bug. I sang gospel music until I was about 13. Then, my mom and dad bought me a country music greatest hits compilation, which included artists like Loretta Lynn, George Jones, Patsy Cline, Waylon Jennings, and others. I fell in love with classic country music. Over time, I became a fan of George Strait, Garth Brooks, Alan Jackson, Jason Aldean, and Chris Young. Once country music grabbed hold of me, it really had a strong grip.

Country music has a way of evoking a sense of nostalgia and taking you to the places described in the songs. I’ve found that the country music industry has a unique, close-knit feel compared to other music capitals. While some of that small-town charm is fading, the industry still maintains a sense of camaraderie.

Absolutely. Nashville has changed a lot, but there’s still a sense of community among those in the industry.

Who would you say were your biggest influences from the classic country era?

From a classic country standpoint, George Jones is a big influence. In the Callaway household, George Jones is considered the greatest of all time. My dad jokes that I’m his second favorite country singer. For me, Garth Brooks is the artist who made me want to be a country artist. His impact is huge, and his live performances and songwriting are incredible. George Strait is another major influence. When I started playing and trying to make a living, Jason Aldean was at the top, and I looked up to him a lot.

It’s great to have those influences, and they provide a framework for your own journey. How long have you been playing guitar?

I started playing guitar around the time I began writing songs, which was around age 13. I had written a song that was more like a poem. I had a melody in my head but didn’t know how to play guitar, so I learned to play in order to write music. Singing always came first for me, and guitar playing came later. Now, playing guitar is second nature.

You’re on the road quite a bit. Garth Brooks changed the game in live performances, and though there were other pioneers, his approach was unique. I’ve worked with people like Tom Jackson, who is one of the best at live performance coaching. Garth has a way of connecting with the audience and making everyone feel included. He looks out at the farthest point in the venue and thinks about how to reach everyone.

That’s right. He has a special way of engaging the audience.

And not all artists do that. I’ve learned from Tom that songs shouldn’t all look the same on stage. George Strait, for instance, can get away with a simpler setup because of his incredible voice. But for most artists, the stage presentation should vary to match the different emotions of the songs.

Absolutely. I strive to keep my shows engaging and to connect with the audience in a meaningful way.

What’s your favorite part of your current show?

I’m not a fan of set lists; I prefer to adapt based on the audience’s response. But I’ve realized that for hard ticket events, having a rehearsed show is important. I enjoy connecting with the audience and making them feel like the experience was special. Whether they’re going through a breakup, thinking about marriage, or dealing with a personal loss, helping them feel something is the reason I do this.

That personal connection is crucial. It’s similar in comedy, where crowd interaction can be a highlight. Matt Reif’s success, for example, is partly due to his crowd work. Even if you have a set list, those spontaneous moments are important.

Definitely. I’ve learned to balance between having a structured show and being open to those impromptu moments that make a performance memorable. You’re giving me the evil eye, but I’d say my favorite part of the show has got to be “Horses in Heaven.” That song is the number one request at my shows, along with “Worth a Shot.” “Horses in Heaven” holds such deep meaning for me, and it’s probably my favorite part of the show. It’s kind of in the middle, after warming up with some barn burners, and then hitting them with something real. That’s definitely my favorite moment.

Let’s talk a bit about what fuels your live performance. When you’re playing clubs and festivals, getting people to show up is a big challenge. It’s a crucial aspect of perseverance in the music industry. With platforms like Spotify, the focus is often on the platform itself rather than the artist. It’s not a negative critique; their job is to maximize their reach. Often, listeners love a song but don’t know who’s performing it because the artist hasn’t properly branded themselves. This issue is prevalent even with major artists.

Before all this changed, artists like the Grateful Dead, Jimmy Buffett with the Parrot Heads, and Garth Brooks understood the value of building a “tribe.” They knew how to create a long-term fan base.

Speaking of Nashville, how many times did you hear “no” when you moved there?

That’s a great question, Terry. I heard “no” a lot. But the key is to be determined and not let rejection stop you. If you’re determined, it’s just a matter of finding the right opportunities. Before moving to Nashville, I was playing in Myrtle Beach, where I had become quite well-known. It was great to be recognized and appreciated, but when I moved to Nashville, I had to start over. The town was there before I arrived and will be there long after I leave. It’s a humbling experience. One significant factor in gaining momentum was Jeff Reed at The Local Nashville. I played there every Friday night with my band. Jeff was one of the first people in Nashville outside my immediate team who believed in me. His support was invaluable and playing at The Local has been crucial to building my name there. I’m excited to do my first showcase there on September 25th as a way to give back and show my appreciation.

If you expect to go to Nashville and not hear “no,” be prepared for it. Rejection is part of the process, and it can be tough, but it also fuels you to keep going. Sometimes, it’s a matter of navigating through the “no” to find the right people who will say “yes.” Reflecting on why you heard “no” can be a learning experience, helping you understand what you might need to change or improve.

Even in relationships, rejection can lead you to the right person, ultimately making you happier. It’s similar in the music industry—rejection is a part of the journey to finding success.

After this, we’ll talk about your website and your gallery. Your online presence is impressive. Your website includes recommendations, an EPK, and a well-curated gallery. What was your thought process behind that?

When we cut a song, we do a photo shoot specifically for it. We’ve been fortunate to work with great photographers and videographers who really understand my vision. Elliot, who does most of my photography, is fantastic at making me look good. I’m glad you’ve noticed and appreciate it.

You were touching on songwriting, which is indeed relevant. If writing isn’t your strength, collaborating with those who excel in it can help you grow as a writer. Surrounding yourself with talented songwriters can elevate your craft. If you’re the smartest person in the room, you’re in the wrong room. Growth comes from being around others who challenge and inspire you. We can discuss more about your songs, like “Forgotten Man,” which is your high-stream song, and your latest track, “Backroad Believer,” when we talk about your album. We’ll take a short break and return to discuss streaming and your new album. Stay tuned for more after a word from our sponsors.

Welcome back to Local Music Somewhere. I’m here in the studio with Trey Calloway, an incredible new country artist. I say “new,” but Trey’s been making music since he was 13. He’s still relatively young, but he’s been on the road for quite a while. When I first started following your career, Trey, I noticed the early struggles you faced. It seemed like there was a significant shift in your career around the pandemic or shortly after—a shift in your numbers, dates, videos, and the quality of your music. Since then, you’ve released some fantastic material.

Thank you, sir.

Of course! We’ve talked about your song “Forgotten Man,” which features a powerful two-verse take on the unsung heroes: one verse about farmers and another about soldiers. That track really caught attention. I did some research and saw that you’re now over a million streams on Spotify.

Actually, we’re probably closing in on two million now.

That’s incredible! Can you share what led to this change?

Absolutely. It’s an interesting story. During the pandemic, everything shut down, and I had a hard time making a living through music. I ended up going back home to work with my dad, who builds commercial playgrounds. It’s tough, back-breaking work. I remember one day, I was out in the blistering sun, doing some heavy labor, and it felt like I was going to pass out. I had this moment where I felt like I was being told that this wasn’t my path. I realized that I shouldn’t let anything stop me from pursuing music. I went back to Nashville and decided to keep going.

That’s a powerful story. I know many artists face similar struggles. It’s inspiring to hear how you turned that challenge into motivation. You’ve also mentioned that music can offer relief and celebration for people going through tough times or happy moments. It’s clear that your music has touched many lives.

Exactly. Every song is a chance to connect with someone, whether it’s through a celebration or a difficult time. I had a particularly memorable experience with my song “Horses in Heaven.”

Let’s talk about “Horses in Heaven.” What makes it resonate so well with people?

“Horses in Heaven” was initially about losing a best friend. The song’s hook, which was Doc Lewis’s idea, really struck a chord. Although the song started as a general reflection on loss, for me, it became a tribute to my friend Andrew, who passed away from a drug overdose. Every time I perform it, I think of him, and it has become a way to remember him. The song’s impact is evident in how it has moved listeners, like the biker who came up to me after a show, crying and sharing how it reminded him of his dad.

That’s a beautiful example of how music can deeply affect people. It’s clear that your lyrics and performances have a profound impact.

Thanks, buddy. I believe every artist, no matter their genre, has the potential to touch lives in a meaningful way. For me, country music has always been about delivering heartfelt, genuine messages.

Absolutely. Your new album is set to drop on September 27th. Where can listeners find it?

It’ll be available everywhere—Spotify, Apple Music, Amazon, and any platform where you stream music. Just search for Trey Calloway.

And you’ll also have a page on rbeatz.com

Yes, that’s right.

Great. The album will feature all the singles released this year, including “Back Road Believer,” “Miss Gone by Morning,” and “Neon Lies.” You’re also already working on new material for another album.

That’s correct. I’m excited about both the new album and the next one in the works.

That’s fantastic. And congratulations on your upcoming wedding on October 12th!

Thank you! I’m marrying the love of my life, Raina. She’s amazing and has been a huge support.

That’s wonderful to hear. Your dedication to your music and your personal life is truly inspiring. Before we wrap up, is there anything else you’d like to share?

Just that I’m grateful for the support and looking forward to sharing more of my music with everyone.

We’re looking forward to it too. Thank you for being here, Trey. We’ll take a quick break and when we return, Trey will perform a couple of songs live. Stay tuned and maybe call some friends to join us. You won’t want to miss it!

Looking forward to it.

Thanks for tuning in to Local Music Somewhere. We’ll be back shortly with Trey Calloway performing live.