Texas-born singer-songwriter Kayla Ray embodies the D.I.Y. spirit of independent artists, whether she's pounding the pavement on tour or connecting online with her growing audience. Her story so far proves that while there's nothing wrong with landing a big-label deal or having a fully-staffed team handling your business dealings, creative dreams can come true without either resource.
As backstories of current artists with unquenchable thirsts for traditional country music often begin, Ray learned to love the genre while being raised by her grandparents.
"I'm from Waco, Texas and Hank Thompson was from Waco. [My grandmother] was just a Hank Thompson nut," Ray told Wide Open Country. "In our house, that was what we were listening to. It also has to do with real-life that was kind of happening around me. I can remember as early as 4, Tanya Tucker was my favorite then. Which is so funny because that was so progressive for my grandmother, but she let me listen to it anyway. As long as I can remember, it's been a huge part of me."
"Right out of high school, I went to this western swing camp," Ray recalled. "My other grandfather was dabbling in real estate, and he sold this property. He just as a whim kind of pawned me off. Like, 'I've got this granddaughter who makes country music.' His client was one of these western swing people. I loved it, but I was not raised... Those kids had been in fiddle lessons for 15 years, and they're just swing through and through. So I felt a little intimidated, but I went."
"My guitar instructor was Tommy Allsup, which was insane in itself," Ray continued. "We really hit it off. I'd just turned 18. So during the day there were lessons, but at night he and his fiddle playing buddy Bob Boatright would bring out homemade wine and let me sit there and drink with the grownups and just tell these stories that would just blow your mind. At the end of the week, they said, 'You're from Waco. We need to get you in touch with Dick Gimble.' And they did."
Dick, the son of Country Music Hall of Famer Johnny Gimble, redirected Ray from studying to be a teacher to enrolling in music management courses at McLennan Community College (MCC). That decision informs Ray's sustained approach as a self-starter.
"Definitely through the management program, the idea was who else is going to do it, and then once it is time to outsource it, you'll know the job well enough to be able to effectively do so," Ray said of filling roles that get delegated within many artists' teams. "That's kind of been my motto, and I want to build commerce around my art, not the other way around. But really, I was just super poor and didn't have another direction."
Ray began booking her own gigs close to home at age 18. She took a position as Jason Eady's tour manager at 21, which vastly expanded her home state network beyond the greater Waco area.
"That family of people is so close knit that it really seemed like once you started figuring out a little bit how it works, then so-and-so knows so-and-so just over in Midland, and then you're in West Texas and there's a whole 'nother market over there," Ray said of her home state's interconnected music scenes. "You can start building week-long runs in separate directions without over-saturating one place because of its size."
A year after an out-of-state run with Eady in 2013, Ray put lessons learned to that point to the test by striking out beyond Texas on her own.
"Since then, I kind of took the same tactic that I took in Texas," Ray explained. "Like, go out for a week as long as you can stand it or afford it and come back to Texas and make some money and then go out East and come back and then head out West and come back. Now I'm lucky enough to where it's starting to be like cyclical, but that was definitely the model at first. I've just been at it since then."
Independent spirits took a huge hit, fiscally and creatively, in March 2020 when COVID-19 precautions halted tour plans. Like many of her peers, Ray adapted by embracing livestream possibilities.
"The online stuff, prior to COVID I thought it was just plum silly, to be truthful," Ray said. "But it changed everything, and it did give me a new way to artistically focus. Like, building a good library or building a little set or something in a bedroom. As silly as some of it was, it was just something to keep me a little bit grounded."
Ray's first string of online victories came via a collaborative series co-founded by a key figure from her past.
"The Sequestered Songwriters thing that was birthed of that was really helpful for me," Ray said. "[Eady] and [Courtney Patton] started it. We did what we would always do on Merle Haggard's birthday and we had a Hag-off. Then the next week, John Prine died. So we thought we'd all get online and take turns doing a livestream tribute to John Prine. It just kind of kept going from there. Unfortunately, we kept losing people, and we were like, 'Well now we're in it. Who do we want to do this week?' Everybody's audience [having] a place to join together really, really helped my following."
As a solo livestream performer, Ray enjoyed instant fan reactions enough to continue going live indefinitely during her scarce time not spent on America's interstates.
"I started doing a Wednesday night stream that just turned into a mess," Ray explained. "Those people are so much fun. We call it We Do What We Want Wednesday. It's really a series of drinking games more than it's anything. I take liberties I'd never take live as far as requests and just going for stuff. Half the time, I'd fall flat on my face. Those people were very gracious about it."
Ray's pandemic experience expanded her catalog beyond "The Jameson Waltz," "Love and Liquor," "Yesterday and Me," Colton Hawkins collaboration "Once a Week Cheaters" and other fan favorites. She recently self-released Songs of Extreme Isolation, Economic Crisis, & Other Funny Things, an album written while sheltering in place. "White Claw Wasted" and "Quarantine Can Bong" find humor in our current situation, while more serious material like the Kristofferson-Esque "If Freedom is What We're After" serves as an introduction to Ray's knack for songs grounded in honky-tonk attitude and classic country storytelling.