Daily Inspiration: Meet Trey Calloway

Today we’d like to introduce you to Trey Calloway.  

Hi Trey, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstories with our readers?
I’m a country singer-songwriter born in North Carolina. The son of a preacher man, I grew up singing in church and was a seasoned performer by the age of 10. Southern and contemporary gospel were my first musical loves, but I was instantly mesmerized by the sounds of country music after hearing songs from the Garth Brooks Greatest Hits album that my parents bought me. At that point, a passion for the rocking, boot-stomping, country music of artists such as Garth Brooks, Clint Black, Alan Jackson, and Travis Tritt started growing within me. I began writing songs, playing guitar, and performing in clubs at the age of 15 and knew early on without a doubt that I’d make music my career. I fronted multiple bands in North Carolina before moving to North Myrtle Beach, South Carolina in 2016 where I formed The Trey Calloway Band. I’ve been playing the eastern circuit ever since and have recently moved into the Nashville spotlight as a regularly featured act at the legendary Alan Jackson’s Good Time Bar. 

I recorded and released my debut Nashville album Carolina Man in 2016 and was able to work with some of my musical heroes including musicians Brent Mason, Lonnie Wilson, Buddy Hyatt, and producer Mike Rodgers on the album. I wrote all 12 songs on the album, including “Daddy from Day One” inspired by the birth of my son Cash in 2014. I was nominated for the Carolina Country Music Awards (CCMA) Male Artist of the Year in 2018, and my original song “Home is Where the Heart Is” won the CCMA Song of the Year as well as Gospel Song of the Year. One of my favorite songs from that album is the title track “Carolina Man” which speaks to my love for the Carolinas, which will always be home no matter where my music takes me. 

After many great years honing my craft in Myrtle Beach, I originally made the move to Nashville in January 2020 and was fortunate to begin playing at Alan Jackson’s Good Time Bar for a few months before the pandemic of 2020. Musicians like me who rely on live performances and crowded venues to make a living suddenly faced unimaginable and unprecedented challenges in 2020-2021. When the Nashville music scene locked down in March 2020, I immediately headed home to the Carolinas and began working a construction job during spring 2020. Fortunately, within a few months, South Carolina and its extensive live music and outdoor venues presented welcomed opportunities that were not readily available for musicians in many areas of the country. I was able to book shows throughout the pandemic in the Myrtle Beach area, and I’m blessed that my career and friendships with fans and new band members flourished during a time when many were out of work. My musical creativity and work ethic were fueled by these challenges, and I wrote 12 new songs and traveled from Myrtle Beach to Nashville recording them during this timeframe, including “One Tough Job” in 2020 and “Karaoke Cowboy” and “Tire Tracks” in 2021. I had the opportunity to record the Tire Tracks EP with Nashville producer Dean Miller, and the title song peaked at #6 on Music Mafia Radio indie charts. “Tire Tracks” recently won the CCMA April 2022 Carolina Artist Showdown and will compete for CCMA Song of the Year in December.

In 2020, under the direction of Carolina-based Stwrongtone Media, I created my first ever music video for my new song “Heal This Family” in a garage in North Myrtle Beach on a small budget. With the help of band members, friends, and family who volunteered to help convey the song’s timely message of love and unity, I was able to share this vision with the world. In 2021, my video for “Heal This Family” was named Social Impact Music Video of the Year by the Josie Music Awards, which is the largest independent music award in the country. I was also honored to be nominated by the Josie Music Awards for recognition as Country Entertainer of the Year, Country Vocalist of the Year, Traditional Country Artist of the Year, and Social Impact Song of the Year. 

In January 2022, I moved to an apartment in Nashville and started performing at local venues including AJ’s Good Time Bar, Lucky Bastard Saloon, Legend’s Corner, The Local, and Tootsie’s. Currently, I regularly perform at AJ’s and my Saturday night shows often Livestream publicly on AJ’s Facebook page beginning at 10:30 pm CST. I travel back and forth between Nashville, Charlotte, and Myrtle Beach spending time with my family, writing and recording original music, and playing live shows, including recent performances at Duplin Winery, Local on the Water, and Boardwalk Billy’s in North Myrtle Beach. I’ve released two original songs in early 2022 recorded with Nashville producer Kevin Key, the most recent being “I Don’t Wanna Love You Anymore” in April 2022 which hit Music Mafia Radio’s Top 30 Countdown on April 18 and aired on The Front Porch Jam syndicated worldwide on April 24. This single has been nominated as 2022 Single of the Year by the Josie Music Awards Association. My next single “Nothing Wrong with A Love Song,” recorded with Nashville producer Lamont Coleman, is a fun summer love song scheduled for release in June 2022!

I’m sure you wouldn’t say it’s been obstacle-free, but so far would you say the journey has been a fairly smooth road?
As discussed, when the Nashville music scene locked down in March 2020, I worked construction for a short period in spring 2020 before the South Carolina music scene re-opened for live performances. This pandemic onset is the only time since I was a teenager that I remember not being able to fully support my family by playing music. Despite financial challenges, I came out of this period even stronger, more appreciative of live music opportunities, and focused on songwriting and original music. I am thankful to my loyal fans who I also consider friends who supported me during this time and even helped me complete a successful Kickstarter campaign to fund the release of my Karaoke Cowboy EP consisting of three original songs. 

My biggest struggles throughout my music career are I’m sure similar to those of other independent artists chasing their dreams to create meaningful music. In addition to working for tips to make ends meet, time management is a daunting challenge because an independent musician wears many hats including a booking agent, band manager, marketing and publicity specialist, songwriter, recording artist, performer, and business manager. Moreover, the business side of a music career can be overwhelming; as a young musician, I never realized I’d need to be savvy with corporate finances and taxes, marketing and publicity, touring logistics, merchandising, contract negotiations and booking, and calendar management. I’ve made mistakes along the way with certain business matters because there’s a learning curve for musicians to develop these business and marketing skills beyond just playing and creating music. I’ve tried to be resilient in the face of such setbacks, which real-life lessons taught my younger self that I wasn’t ready yet and still had skills to develop. These experiences have provided the education necessary for me to become a successful business entrepreneur in the music industry. 

As far as my music, traveling between shows when touring and recording in different cities and states can be tiresome for any musician and challenging for spending time with family. This year I’ve been living in Nashville a lot of the time, and despite the fulfilling music scene and industry and creative talent I meet in this vibrant city, I do sometimes get homesick for the Carolinas, my family, and friends, and don’t like living away from my home. A musician’s life is not always glamorous as people may think, and I do have to remind myself during these times alone in a small apartment living on a budget about why I make sacrifices to create original music to hopefully touch and entertain others. Like most musicians, I also don’t have standard work hours, starting work most often in the late evenings, so my schedule is similar to a third shift worker being up all night and sleeping in the mornings; this schedule can be a struggle, in particular when I have marketing, booking and other job responsibilities that are better suited to being on a regular daytime schedule to coordinate with others. With such an irregular schedule and sometimes playing gigs five times per week, it’s crucial for me to take care of my voice and to do my best not to get sick because otherwise I can’t perform or don’t perform to the best of my abilities. Playing night after night to make a living the way indie musicians do in addition to traveling between different climates, I have unfortunately on occasion had to cancel recording or writing sessions or even shows to take care of myself or my voice, and it’s hard knowing you’re disappointing people when this happens. It’s not easy to go to work sick as a musician so this is always a challenge to find the right balance to keep pushing while staying healthy.

Finally, I’ve had to develop a thick skin to not take industry rejection or criticism personally. My life informs my artistry so when I experience pain, loss, joy, fun, or other emotions, these experiences and feelings often translate into songs. Because of this, at times I’ve felt vulnerable releasing original music when it’s a highly personal endeavor that I pour my heart into. Sometimes I have this same feeling performing when I’m on stage or in a recording studio giving it my all. One example of this that I distinctly remember was a bar owner who was interested in supporting my original music and hiring me to play his venues, while at the same time taking rude jabs at me in front of others because I was not thin enough to be one of his performers. As a professional musician, I’ve had to become more comfortable with myself and self-assured about who I am. I recognize that no matter how hard I try, not everyone is going to like my music or performances, so I use the constructive criticism to become a better person and artist and otherwise do my best to rise above the rejection and scrutiny and use it as motivation to work even harder. There are definitely more “no’s” than open doors along this career path, and because of this, there are times when it’s a struggle to keep making music as a full-time career. My song “Karaoke Cowboy” speaks to some of the struggles faced by anyone chasing their dreams, and I think I’ve tried to put some of my own challenges into this song to help and inspire others to keep it all in perspective. I just continue to work hard, teach myself and learn from others to overcome the obstacles and challenges. I would say to your readers that the support of fans/friends and understanding of the family are priceless to rising musicians, and I will forever be grateful to my fans, friends, and family for taking this journey with me. 

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
As a professional musician, I’m a lead vocalist and play the guitar, banjo, and harmonica. I’m passionate about energizing and inspiring audiences with live musical performances and have played large venues including the Charlotte Speed Street NASCAR Festival and the Myrtle Beach House of Blues. I enjoy the intimacy of playing acoustic shows on my own, but I really love playing in a band sharing the experience with talented and diverse musicians. While country music is, and will always be my first love, I also play rock-n-roll, bluegrass, blues, gospel music, and even the occasional hip-hop song. I’d like to think of myself and my music as a unique mix of old school country and contemporary influence, which I really think will come through in my upcoming June release of “Nothing Wrong with A Love Song.” I travel the eastern U.S. circuit, particularly between Nashville, Charlotte, and Myrtle Beach, performing at clubs, festivals, and private and charitable events. I’ve opened shows for notable musicians such as Joe Diffie, Tracy Lawrence, Pat Green, Edwin McCain, and most recently Trent Tomlinson and am committed to supporting worthy causes through music including at Vet Fest Carolinas, Shriners’ events, and most recently at The Listening Room in Nashville with proceedings benefitting Matthew 25 Ministries. I was honored to be nominated based on volunteerism as a 2021 Male Country Artist of the Year by the Queen City Awards, which funds art-based scholarships for deserving students. One upcoming performance that I’m really looking forward to is playing as a featured artist at the Tennessee State Fair this August! 

While I love performing for fans, I hope that above all I’m remembered as a successful songwriter. My dream is to bring original music to life to help others in whatever way my music might touch them. I have released 24 original songs that are available on music platforms such as Spotify, iTunes, or Apple Music, and I have many more in the works for 2022 and beyond. I’m continuously inspired to write songs and express myself through music. The challenge for me is to find the time and money to record and release the new music while at the same time playing gigs to pay the bills. I was fortunate to complete a successful Kickstarter campaign in 2021 and to have sponsors offset some of the recording costs last year, so I just continue to work hard, keep a positive attitude and count my many blessings among which are the support system and team of volunteers who have helped me in my professional life. As I mentioned previously, my life often informs my songwriting and creativity. For example, my son who is the light of my life has inspired several songs including most recently “Karaoke Cowboy,” while I wrote “One Tough Job” about my dad, and “She Loves Me” and “Til You Came Around” were written for my girlfriend. To date, I’ve written all 24 original songs I’ve released but being in Nashville this year I’ve had the opportunity to collaborate and write music for the first time with other artists. I’ve really enjoyed this camaraderie and new friendships, and I’m looking forward to releasing a couple of new songs in 2022 that I’ve co-written with others. 

Recently, I received 2022 Songwriter Achievement recognition from the Josie Music Awards for four yet-to-be-released singles written both solo and with these Nashville co-writers. I was also named as a finalist by the International Singer-Songwriters Association (ISSA) for 2022 Songwriter of the Year and Rising Star of the Year, and my song “Karaoke Cowboy” is a finalist for Single of the Year. In addition, I received nominations for ISSA Entertainer of the Year and Vocalist of the Year. Recognition as a songwriter means a lot to me, particularly for this song “Karaoke Cowboy” which is about a musician with a family chasing his dreams. The Josie Music Award nominations for 2022 were also announced the first week of May, and in addition to the Josie nomination for Single of the Year, I am nominated for Country Artist of the Year and Country Male Vocalist of the Year. I’ve made plans to attend the Josie Music Awards ceremony taking place in October at the Grand Ole Opry House in Nashville. I can’t imagine being able to set foot on the Opry stage to be recognized for my music, but I know I’m already so blessed to even be this close to having the opportunity! I encourage readers to check out my website and follow me on social media and streaming platforms to support my music and catch a live show.

Do you have recommendations for books, apps, blogs, etc.?
While there are no specific or “go-to” resources that I frequent, I often watch or read podcasts, blogs, and articles about music marketing, particularly digital marketing, and music platforms or streaming services and their algorithms to help me do the best I can to bring my music to my fans and potential new fans and to industry experts. There’s never been a better time with resources for indie artists to promote their own music, but there’s an expertise to marketing and publicity that isn’t always common knowledge or intuitive. One thing I would recommend for any young musician is to study marketing and business to develop the knowledge and tools that you’re going to need to be a successful musician. Not everyone knows this, but Garth Brooks was a college advertising major, which I’m sure served him well becoming one of the best-selling country artists of all time. Personally, Garth is my favorite country artist and the one who got me started listening to, writing, and playing country songs! Through these online resources, I educate myself about marketing and the industry, and I’m still learning as I go. 

In my free time, or more like the time I need to just take a break and relax, I’m a history buff and watch online podcasts about U.S. and world history. I really enjoy watching movies late at night when I don’t have a gig and can’t sleep because of the work schedule I keep. I just got the DVD for Eddie and The Cruisers, which is one of my favorite older movies, and I never tire of watching it, its sequel, and listening to the soundtrack. My biggest guilty pleasure is being a Trekkie and enjoying all things Star Trek, which is an interest I share with my mom. I think these hobbies are important to destress when needed and occupy my mind late or middle of the night so I can be my best self with my work and friends and family. 

Contact Info:

• Email: treycallowaybooking2@gmail.com
• Website: https://treycallowaymusic.com/
• Instagram: https://www.instagram.com/treycallowaymusic/?hl=en
• Facebook: https://www.facebook.com/treycallowaymusic
• Youtube: https://www.youtube.com/channel/UCwkuwhMIj-wXYv53xdxw71Q?app=desktop
• Other: https://open.spotify.com/artist/2fGDZGiDyQfDq5J9XPtz8s https://music.apple.com/us/artist/trey-calloway/1163336961

Image Credits
Christy Hunter
Tony Murnahan
Karla Pulido
Allison Hartman