Conversations with Drew Gregory

Today we’d like to introduce you to Drew Gregory.

Hi Drew, please kick things off for us with an introduction to yourself and your story.
I’m a small-town farm kid from Southern Alberta, Canada. I picked up the guitar and started playing when I was about 15. It took me a few years to start singing and writing. In 2009, I decided to pack up the truck and head to Nashville to pursue greater success and knowledge in the country music industry. That was the real beginning of music as a career for me. Coming from a small town where I was the only one who sang and played, I started to think I was getting pretty good but was very quickly humbled during that first trip by the amount of talent in Music City.

This encouraged me to work even harder at my craft, and I began to fall in love with the city that still had the small-town feel I needed, with a concentration of talent that allowed me to learn and grow into the artist I’ve become today.

Since that first trip, I’ve been steadily back and forth from Alberta to Nashville every year, spending summers on our family farm in Alberta while playing the Canadian festival scene and spending the winters writing songs and building connections in Nashville.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
I feel very fortunate with who I’ve been able to work throughout my career as a songwriter, but of course, there have been struggles along the way. As with any artist at the start of their career, there’s a period where you think you are capable of the bigger stages or higher chart positions at radio, and that comes with a lot of inner turmoil. When you work for two years on an album to have someone tell you it’s not good enough, it’s always difficult to swallow.

But it ultimately makes you better, and looking back, the whole journey has been a lot of fun. Nowadays, my goals have more to do with things I know I can control, and I make sure with each goal I set that I will enjoy the process of getting to that goal.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
We’ve really concentrated on this question over the last few years.

What sets us apart? Our family has a small grain farm, and I’ve leaned into that with my music and online presence. I’ve always had some very rural aspects to my music, but I did not think the farming side of my life was as attractive to people until we really started posting about it online and realized we have a lot of fans that range from farmers themselves to people who have never been on a farm but love to see what it’s all about.

I also grew up on a lot of classic rock and roll in the house, so I think the authentically country lyrics combined with production that tends to lean more to the rock and roll influences gives us a bit of a unique sound.

We’d love to hear what you think about risk-taking.
Quitting my job and taking that first trip to Nashville was probably the biggest risk I’ve taken. This was at a time when I’d never even played a live show for money. I don’t think of myself as a huge risk-taker, but there was something just pulling me to do that, and I could not deny it.

I’m so glad I did it looking back. That gave me more confidence in taking other risks necessary to continue to grow my career. I encourage others to at least take that first initial jump to see if it’s something that can work for them. I loved the line that I’d rather regret something I did than something I didn’t do, and despite being careful in calculating risks, I still try to live by this since that first trip!

Contact Info:

• Website: www.drewgregorymusic.com
• Instagram: www.instagram.com/drewgregorymusic
• Facebook: www.facebook.com/drewgregorymusic
• Twitter: www.twitter.com/drewgregory_
• Youtube: www.youtube.com/drewgregorymusic
• Other: www.tiktok.com/drewgregorymusic 

Image Credits
Michelle Spice Photography