Truth be told, after I scheduled my interview with 21-year-old Nashville singer-songwriter Ainsley Costello, I had second thoughts. Not about her—her music struck me as both well-crafted and heartfelt, with an authenticity in her songwriting that many artists work years to find. And I thought (rightly so) that chatting with her would be a lot of fun. My concern, honestly, was for her. I reached out to her publicist and asked, “Has she seen my show? Does she know who my audience is?” In other words—does she realize she’s about to chat with a guy who could be her dad?
Maybe I’m not quite a geezer, but let’s be real—Ainsley’s music wasn’t exactly written with middle-aged guys like me (or my audience) in mind. Still, her publicist assured me that she was genuinely excited to connect with a wider audience, and with that, I stood down and got to work preparing for our conversation.
What I found surprised me. Not only was Ainsley well-spoken and thoughtful beyond her years (and forgive me if that sounds condescending—I remember my 21-year-old self, and let’s just say… yikes), but her experience in the music industry so far has already given her a level of insight and business savvy that many seasoned musicians would envy.
It’s no secret that the music industry today barely resembles the one that launched the careers of the artists I usually feature. Labels aren’t throwing money around, and long-term success now demands a mix of creativity, entrepreneurship, and a willingness to embrace tools and platforms that some of us can barely pronounce.
So yeah, I went into this wondering if we had much common ground — and came out a fan, not just of her songs, but of how she’s navigating this wild new version of the music world. Ainsley gets it. And more than that, she’s thriving in it.
And damn it all – she really knows how to write a great hook…