"Man, he was so awesome to us!" Anderson says of Chesney. "That was the first real lesson we got to learn about what it takes, how much it takes to put on that type of show, and to watch him work. We don't hang out or have beers together, but any time I've seen him he's always offered any support he could."
What he couldn't have known at the time was that he was finding his footing in country music when the genre itself was at a crossroads. Growing up in Southern Indiana, Anderson says he was exposed at a young age to country songwriters like Conway Twitty, but he also was the right age to appreciate John Mellencamp, Garth Brooks and KISS. With his own performances drawing comparisons to Jarrod Neimann, Luke Bryan and Eric Church, artists who were also inspired by a similar melting pot, things start making sense after all.
"I think it's very exciting, country music is in a whole new phase of life right now, creating its new sound," he says. "There's still a lot that's 'pop' to it, but there's also a lot that drives back to classic country. I grew up worshiping John Mellencamp, that's where my roots are for sure in songwriting. And if Mellencamp was coming up today, I think he'd definitely wind up more in country."
Anderson's first trips to Nashville didn't necessarily turn out how he'd hoped. "They told me my demos sounded solid, but too much like Luke Bryan," he says. "Nashville's funny that way." So he turned back to the road, honing his chops by playing the college circuit, in turn developing a loyal fan following.
"Being from Bedford, obviously Bloomington was right in my back yard," he says. "I didn't apply to any other schools, I knew I wanted to go to Indiana. And now I have the most supportive fan base of people who graduated and moved to places like Chicago, Atlanta, New York City. We're selling a lot of downloads in these big cities because it started there in Bloomington."
His first Nashville album, Torn Jeans & Tailgates, yielded a few songs that got minor radio play, but for the most part he was finding his way as a songwriter, unsure when to push his own material and when to rely on the songs of others. Over the years, however, he's built up the confidence to know when he's found a winner.
"My first record I put out had a lot more "songwriter" songs on it," he explains. "I was still a bit green, and my songs tended to be riffs on the Jerrod Neimann sound at the time, so I left most of them out. But on my last record I wrote a lot of the songs myself. And when you're writing them yourself, it's a lot easier to focus on the story. The more I've spent time in Nashville, the more I've found myself wanting to write more of my own songs. But every song I have recorded that's not mine, I found myself thinking 'Damn! That song was written for me! That's my life!'"
On Spotify, where his latest single "Your Love is Like Country Music" has been played more than 2.3 million times, Anderson says country music leads the way in exposing younger audiences to more variety than radio can necessarily offer.
"We played a show in Minneapolis and I look out there — I've never even been to Minneapolis! — and I can see all these people out there singing along!" he laughs. "That's the coolest thing for me, and country music is really changing in that it's attracting lots of people to hear new music on streaming services. It costs a lot of money to play the 'radio game,' so it's incredible that on Spotify we've had more plays than some signed artists."
It's all about being patient, he says, and doing the hard work now to ensure his music is heard even if a major label never calls. "We could be on a major label but then we'd risk getting lost in the shuffle. There's no guarantee, so I'd rather work hard at building our fan base. It's been too much time and sacrifice to just give that freedom up for nothing. Then you never would hear from me. At least this way we get out there and tour, we have fans showing up from all over."
Before heading back into the studio next week to begin recording his latest project, Anderson is excited to return to The Vogue ("one of my favorite venues!") where he's had the opportunity to headline on more than one occasion. "We're hoping to see another big crowd and get crazy," he says. "It's such a cool venue, I always look forward to getting back there to see a bunch of familiar faces. That's what's great about playing Indianapolis — we get the people from southern Indiana who travel in for the show, and the people from Indianapolis seeing us in their backyard. And it's a fact, nobody puts on a better show than Indianapolis in my book."
Half the fun for Anderson, it would seem, is in putting on a great country show in an intimate venue where fans are likely to remember the experience.
"For me it's all about playing shows, that's where my heart's always been," he says. "I live for it, I couldn't imagine what else I'd wanna do. I remember when I opened up for Luke Bryan one time, and he was awesome but he wasn't as famous as he is now. Or when I saw Jason Aldean before he blew up, he played a bunch of John Mellencamp covers in Bloomington, all these songs that we all knew. Those are the shows I like to read about. I always wanna know what bands felt like at the last show they had before their big break. What was it like? No one ever asks me that."