Drew Taylor on the Nashville Grind, Brantley Gilbert’s Full-Circle Gift, and Why Success Is Just Showing Up
I had the pleasure of talking with Drew Taylor, a man who seems to understand that in Nashville, the overnight success story is usually a myth told to tourists. For Taylor, a Waterloo, Ontario native who traded the Canadian cold for the neon humidity of Broadway, the journey hasn’t been a sprint; it’s been a slow, deliberate burn, not unlike the whiskey he sings about in his latest tracks.
To understand Taylor’s trajectory, you have to look at the bloodline. He grew up in the shadow of the stage. His father was a touring musician, a road warrior who spent time playing alongside titans like George Strait and Kenny Rogers. But the introduction to the family business wasn’t exactly smooth. In a moment that feels ripped from a sitcom, Taylor recalls his father’s attempt to fast-track him into show business at age eight.
“He tried to get me to be an Elvis impersonator,” Taylor says with a laugh. “He tried to throw me in the jumpsuit, and that scared me away from music.”
The jumpsuit stayed in the closet, and Taylor stayed away from the microphone, at least until adolescence hit. At fifteen, he picked up a guitar, and the inevitable pull of genetics took over. However, the path to country music wasn’t a straight line. Before he was writing ballads about red wax and heartbreak, Taylor was fronting a Screamo band, sharing bills with heavy hitters like Underoath and Atreyu. It was a loud, aggressive detour that eventually gave way to a career as a firefighter and an entrepreneur. But the music always lingered, a low hum in the background that eventually became too loud to ignore.
Taylor arrived in Nashville in 2015, a Canadian looking for a foothold in a town crowded with hopefuls. It was a move facilitated by serendipity and bold networking. He had befriended Brantley Gilbert’s band, and when it came time to cross the border for good, he called in a favor. “I said, ‘Hey, I need a visa sponsor… and I need help getting over here,’” Taylor recalls. The band stepped up, signing the paperwork and giving him work in the studio and on Broadway.
It was a full-circle moment that recently culminated in a way most songwriters only dream of. Taylor, a lifelong fan of Gilbert, was recently gifted a song by the country star to cut as his own. “It’s funny how my biggest influence gave me a song to cut,” Taylor says. “It’s a beautiful song, and I can’t wait to release it.”
Despite the accolades, including a Number One spot on Sirius XM’s Top of the Country for “Wish I Didn’t” and a Wildcard win at the Boots & Hearts Emerging Artist Showcase, Taylor resists the urge to romanticize the struggle. When asked about his big break, he offers a sobering correction.
“It’s just been a grind, this whole thing. I feel like there hasn’t ever really been a break,” he admits. “It’s just grind every single day, and I don’t think I’ve actually worked this hard up to this date.”
That work ethic is currently being poured into a heavy release schedule for the coming year, spearheaded by his single “MAKERS.” The track captures the intoxicating, blurry line between a whiskey buzz and falling in love, a theme that fits comfortably in the modern country canon. But Taylor insists the new material is about more than just checking boxes for radio play.
“With this new music, [it’s] just honesty,” he says. “Not so much just chasing that pop radio sound… A lot of these new sounds are honest and they come from the heart.”
The modern music industry, however, demands more than just honesty and a guitar. It demands content. Taylor speaks candidly about the challenge of balancing artistry with the relentless algorithm of social media, a hurdle that didn’t exist when his father was touring with Rogers. “You’re taking care of everything else and you have to come up with content,” he says, noting the struggle. “I know it’s a struggle for a lot of artists right now.”
At 34, Taylor seems to have found a philosophical rhythm to match his musical one. He isn’t chasing a specific trophy or a stadium tour, but rather a sustainability that allows him to keep playing. He mentions advice from a former manager: “You need to enjoy the ride or you’re not gonna enjoy any of this.”
It is a mindset necessary for survival in a town that eats its young. Taylor is focused on the present, on the songs he has held onto for years that are finally seeing the light of day, and on navigating a divided world. He mentions a new song he wrote recently with the hook “Can’t We All Just Get Along,” a reaction to the polarization he sees in the world.
“I think people just need to understand one another and have the conversations,” he muses. “Sitting down over a beer and just having the conversation.”
For now, Drew Taylor is doing just that, one song, one stage, and one conversation at a time. He is a long way from the Elvis jumpsuit, and a long way from the firehouse in Ontario, but he seems to be exactly where he is supposed to be: in the grind.
“I feel like there’s no definition of success for me in this industry,” Taylor concludes. “It’s just grinding every day and taking every win that I can get.”
Yitzi: Drew Taylor, it’s so nice to meet you. Before we dive in deep, our readers would love to learn about Drew Taylor’s personal origin story. Can you share with us the story of your childhood, how you grew up, and the seeds for all the amazing work that has come since then?
Drew: My dad used to be a musician. He still is, but he used to do the touring thing, and it’s been engraved in me since I was a child. Funny story, he tried to get me to be an Elvis impersonator when I was like eight. He tried to throw me in the jumpsuit, and that scared me away from music. But then I ended up getting back into it around fifteen. I got my first guitar, and the rest is kind of history.
Yitzi: Can you tell us a bit about some of your first breaks, opportunities that really cemented you in the industry?
Drew: It’s just been a grind, this whole thing. I feel like there hasn’t ever really been a break. I’ve been doing this a long time. I think you get to a point where you develop as an artist and as a man; you grow up, and your music evolves and changes. There’s really been no break. It’s just grind every single day, and I don’t think I’ve actually worked this hard up to this date.
Yitzi: You probably have some great stories from all the different parts of your career. Can you share with our readers one or two stories that most stand out in your mind from your professional life?
Drew: We’ve had so many funny stories. I don’t know if they’re PG though. But I’ll tell you a really cool story. I’ve always loved the artist Brantley Gilbert, and I met his band back in 2015. We became friends with the band, and when I wanted to move down here to Nashville, I contacted them. I said, “Hey, I need a visa sponsor,” because I lived in Canada, “and I need help getting over here.” They were awesome. My buddy Noah signed the visa, and we worked for him in the studio doing background vocals and down on Broadway when we first got here. Full circle moment: last week Brantley Gilbert gave me an absolute hit song. It just resonated with me. Being one of his biggest fans, it’s funny how my biggest influence gave me a song to cut. It’s a beautiful song, and I can’t wait to release it here in the next few months.
Yitzi: It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a funny mistake that you made when you were first starting in the industry and the lesson that you took away from it?
Drew: I feel like if I worried about all the mistakes I made, I wouldn’t be in this industry. I feel like there’s no right or wrong road. Everything that I do is just a learning experience. I’m enjoying the ride right now, and even the little mistakes I make are learning experiences for me.
Yitzi: There’s a saying that “No” is not rejection but redirection. Do you have a story where you got a no, but that led to an unexpected discovery or opportunity or success?
Drew: I feel like there’s no definition of success for me in this industry. It’s just grinding every day and taking every win that I can get. Just enjoying where I’m at consistently. My first manager always told me, “You need to enjoy the ride or you’re not gonna enjoy any of this.” If you get your first number one, what comes after that? Is it a Grammy? And you’re still not satisfied? So you have to be satisfied where you’re at. Being 34, that’s what got me through it up to this point. It’s been a long ride.
Yitzi: What’s been the most challenging project or role you’ve taken on so far and why?
Drew: I would say social media. When I first got into this industry, that really didn’t exist; it was just about good music. Even five years ago, I knew everybody wanted that, it was the thing, you had to do social media, but now it’s engraved. This year has been such a hurdle. You’re taking care of everything else and you have to come up with content. It’s very challenging, and I know it’s a struggle for a lot of artists right now.
Yitzi: Please tell us about the exciting new projects you’re working on, new albums, new EPs, new releases. We’d love to learn more.
Drew: We’re on a pretty heavy release schedule for this year, so I’m pretty excited. A lot of the songs I’ve been working on throughout my career I’ve kind of held on to. We got a lot of great songs coming out this year, and I haven’t been more excited.
Yitzi: If you could take all of your music, the lyrics, the album covers, the melodies, put it in a blender and blend it up, mix it all together, what would be the overall message that comes out of that mixture?
Drew: With this new music, just honesty. Not so much just chasing that pop radio sound. A lot of these new sounds are honest and they come from the heart. My wife makes a lot of the album covers; she puts a lot of work and energy into that. We’re just excited, just honesty and me.
Yitzi: This is our signature question that we ask in all of our interviews. Drew, you’ve been blessed with a lot of success now and you must have learned a lot from your experiences. Looking back to when you first started music, can you share five things that you’ve learned over the years that would have been nice to know when you first started?
Drew: I would say networking was a big one. Knowing what I know now about the industry, but you can’t go back on it now. It’s knowing what to do in the industry. I feel like the songs, that all comes, that takes years to do. But networking, becoming the man you want to be, and becoming the artist you want to be kind of happens at the same time. And just being true to myself.
Yitzi: Can you share some of the self-care routines that you do to help your body, mind, and heart to thrive?
Drew: Water. Water. I wish I could say I work out. It’s funny, I bought a gym membership last year and I’ve been three times. That’s on the agenda for ’26. But we’ll have to see. Drink a lot of water.
Yitzi: So this is our aspirational question. Drew, because of your amazing work and the platform that you’ve built, you’re a person of great influence. If you could spread an idea or inspire a movement that would bring the most amount of good to the most amount of people, what would that be?
Drew: That’s a hard one. I wrote a song two weeks ago, and the hook was “Can’t We All Just Get Along.” Meaning there’s a lot of division right now with a lot of different things, and I think a lot of people are confused right now and they don’t even know what they’re arguing about. It’s just so many different topics; you can have the left arguing with the left on things and the right arguing with the right on things. Can’t we all just get along? I don’t think that anybody has enough influence and power to change anything right now. I don’t know what the answer to that is. If I knew, I would be doing it. But I think people just need to understand one another and have the conversations. The conversations aren’t being had enough. Sitting down over a beer and just having the conversation. People are just in denial about each side and they are so firm on it. So, “Can’t We All Just Get Along.”
Yitzi: How can our readers continue to follow your work? How can they purchase your music? How can they learn more? How can they support you in any possible way?
Drew: You can follow me on www.drewtaylorofficial.com. I’m drewtaylor_official on all social media platforms.
Yitzi: Drew, it’s so nice to meet you. Wish you continued success, good health, and blessings and I hope to do this again next year.
Drew: Happy holidays. Thank you so much.
Drew Taylor on the Nashville Grind, Brantley Gilbert’s Full-Circle Gift, and Why Success Is Just… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.