Aaron Chesling shared their story and experiences with us recently and you can find our conversation below.
Aaron, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What is something outside of work that is bringing you joy lately?
Lately, I’ve been getting a lot of joy from a mix of hands-on and creative hobbies. I love spending time outdoors hunting when the season’s right, and I’ve really gotten into smoking meats—there’s something satisfying about the process and the patience it takes. I’m also always working on some kind of house project, whether it’s building, fixing, or upgrading things around the place. On the creative side, I’ve always loved painting and making art—it’s a great outlet that balances out the more physical stuff and lets me express a different side of myself.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Aaron Chesling—a producer, songwriter, guitarist, and A&R rep based out of Nashville. I started my career on the road as a touring musician, then spent years behind the scenes at major labels like Universal and Big Machine before launching my own independent label and creative company, Asphalt Music Group.
These days, I’m working with artists from all over the country, producing a wide range of singles and records—everything from stripped-down singer-songwriter tracks to full-band country and rock records. What I love most is helping artists develop their sound and bring their vision to life, whether they’re just starting out or already well into their careers.
At the core of what I do is a balance: the industry experience to know what works, and the creative freedom to do things differently. I’m a guitar nerd at heart, a big believer in honest collaboration, and someone who genuinely loves building long-term relationships with the people I work with.
Above all, I want to create music that feels real—and help others do the same.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What’s a moment that really shaped how you see the world?
A moment that really shaped how I see the world was when I first stepped away from the major label system and started working directly with artists on an independent level. It made me realize how much incredible talent exists outside the traditional industry structure—and how many of those voices just need someone to believe in them and help bring their vision to life.
That shift taught me the value of creative freedom, the importance of listening more than talking, and that success doesn’t always follow the same path. It completely changed how I approach my work, and honestly, how I approach people in general—with more patience, intention, and respect for different journeys.
What did suffering teach you that success never could?
Suffering taught me patience, humility, and how to let go of control—things success never really asks of you. When life’s running smooth, it’s easy to think you’ve got it all figured out. But during the hard seasons—whether it’s career setbacks, creative ruts, or personal struggles—I had to slow down and get honest with myself.
What really carried me through was leaning on my wife, my kids, and my faith in God. They reminded me what really matters, and they kept me grounded when everything else felt uncertain. In those moments, I learned to listen more, to show up even when I didn’t feel like it, and to trust that things were working together for a purpose—even if I couldn’t see it yet.
Success builds confidence. But suffering builds character—and reminds you who and what you truly depend on.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What are the biggest lies your industry tells itself?
One of the more common myths in the music industry is that there’s a formula for success—whether it’s chasing trends, going viral, or hitting certain streaming numbers. And while data and strategy absolutely have their place, they’re only part of the picture.
What really stands the test of time is authenticity. Audiences can feel when something’s real—when an artist is genuinely sharing their voice and not just following the market. I think sometimes the industry forgets that. We get so focused on quick wins that we overlook the slow burn of building something meaningful.
I’ve learned that the best music usually comes from artists who know who they are, even if they’re still figuring out how to say it. And the role of people like me—producers, A&R, creatives—is to help bring that out, not polish it into something it’s not.
At the end of the day, staying authentic isn’t just good for the artist—it’s what makes the whole industry better.
Okay, so let’s keep going with one more question that means a lot to us: What will you regret not doing?
What I’d regret most is not being honest when it really counts. I’m not one to sugarcoat things just to avoid discomfort, but I also try to be thoughtful about how I deliver feedback. If I see potential in someone, I want to help them grow—not just be better, but truly great. Sometimes that means having tough conversations, and I believe those moments are necessary.
I value being direct because I know time is precious, and I don’t want to waste it with unclear communication. But at the same time, I try to balance honesty with respect and care, because growth happens best when people feel supported, not just corrected.
Ultimately, I’d rather risk a hard truth than miss the chance to help someone reach their full potential.
Contact Info:
- Website: https://www.aaronchesling.com
- Instagram: @TheAaronChesling
Image Credits
Kayla Schoen and Hunter Berry
