When Jon Loba made the move to Broken Bow, independent labels weren’t considered “in the game.” But the kid raised in Southern California and on a Michigan dairy farm liked the idea of coloring outside the lines and calibrating to see small wins as real victories. Through his passion for music and work ethic, he took the indie and created a label group that stands toe-to-toe with any of the majors, leading to his being named BMG president of Frontline Recordings, North America.

Lainey Wilson and Jelly Roll have dominated this year’s conversation with their massive hits and certifications. She took the coveted Country Music Association Entertainer of the Year trophy among her four-award haul; he won New Artist of the Year. Jelly was nominated for Best New Artist at this year’s Grammys, while Lainey won Best Country Album. Wilson is speaking up for women’s place in the world; he’s testifying before Congress on the impact of fentanyl abuse in America.

Principled, engaged, singular voices. What began with Jason Aldean’s hard-charging, blue-collar country has turned into massive crossover play for Parmalee and Jelly Roll, as well as retrenching traditional country with Dustin Lynch and Wilson.

Let’s start with the basics.

I was born in the San Fernando Valley and lived there until I was 10. Mom married a dairy farmer on 1,200 acres in Western Michigan, about the time of Footloose. I was living real-life Footloose. My dad still lived in Southern California; I’d spend summers and vacations in the Valley, then back to reality and work in Michigan. It helped me understand and appreciate two different worlds. In Michigan I developed my work ethic. When you’re unfreezing stock tanks at five in the morning, then rushing inside to take a shower and be ready for school, coming back and milking until eight, doing your homework after? Everything I’ve done since is a piece of cake.

I went to Central Michigan University, because they had a good finance program and no social temptations. It was in the middle of a cornfield. Went for a couple of years, then back to California to CSUN for a year. Budget cuts in California meant it was going to take too long to finish, so I finished at Central Michigan. I planned to go to New York to get into an investment-banking training program.

A gentleman we thought was a close family friend turned out to be my grandfather; I realized that during my senior year of college, so I came to Nashville after I graduated to meet that entire side of the family in Cookeville, Tennessee. I fell in love with Tennessee, Nashville, specifically Music Row. I thought, “I don’t know what this business is about, but I’ll play around for a few years, and then I’ll get a real job.”

The playing around for a few years turned into a real job, though it’s never felt like it once. I was at BMI for six months, then Warner Bros. as a promotion coordinator. The general manager at the time, Eddie Reeves, Jim Ed Norman and I were all on an elevator; I was going on about a bunch of things that were happening, Eddie smiled and said, “That’s why we hire young kids.” I said, “Why?” He said, “To remind us how great this business is.” I said, “You have to be reminded how great this business is?” He said, “Give it 10 years; you’ll understand.” Eddie got off on the second floor. Jim Ed and I rode up to the third floor. Jim Ed shook his head. He goes, “Don’t listen to him. If you love music, people and creating musical memories, you’ll love this business forever.” Every day when I leave for work, I think, “I love it now more than ever.”

How did you get to BBR?

I was a coordinator for Warner Bros. for three years, then Southeast regional for Atlantic Records for a year and a half. When I made the Atlantic move, everybody said, “What are you doing? They’re going to close Atlantic down with all the consolidation going on in Warner.” I thought, “If I can get six months on the phones, I can build relationships and be okay.” We made it a year and a half. Scott Borchetta’s dad, Mike Borchetta, was general manager at Broken Bow; he kept calling me.

Independent labels hadn’t had success in decades in Nashville. I thought, “I’m not doing that. That’ll be a graveyard. I’m going to wait it out.” He kept calling, so I threw out a ridiculous number. Five minutes later, he got off the phone with Benny Brown and said, “Congratulations, you’re with Broken Bow.” That was Friday. He goes, “I need you to start Monday.” I came in Monday, said, “Where do I sit?” “He said, “Over there,” where the guy who was the only promotion guy sat. I said, “Where’s he sitting?” Borchetta said, “We had to fire him to afford you.” I said, “All I know is 50 stations that matter, there’s another 100-plus out there.” He said, “Kid, you’ll be fine.”

We stumbled through with a Craig Morgan hit, then a Joe Diffie hit, then a Sherrié Austin hit. I was trying to keep everything small and focused as we built. We had the first indie success in a long time. Then Benny said, “I need you to go to a showcase with me; some guy who’s been dropped from two labels—and he’s going home tomorrow if he doesn’t get a deal.” I thought, “Nobody else wants him; what are we doing?” We went to the Wildhorse Saloon. I said, “Nobody in the industry goes there.” He goes, “You’re right, I want to see how real fans react.” That was Jason Aldean. We sat there; he said, “I’ve seen enough, let’s go sign him. I think Jason’s going to explode.”

Off we went. He said, “Don’t you like the music?” I said, “I love it. It’s not country, it’s metallic country.” He goes, “You’ll figure out how to get this on the air.” I thought, “I can’t get that played.” It was a matter of survival. At a Clear Channel showcase, I was so nervous introducing him I was shaking. My introduction was so bad, no matter what, he’d look good. Gregg Swedberg said, “He’s pitchy as hell, but he’s got something.” There were 10 guys in those early days I could count on when they had no reason. Doug Montgomery was another one. We were hanging on by our fingernails. Benny’s stubbornness to not give up; most guys with money that came to Nashville tap out at about $5 million. Benny lost seven or eight, and I don’t think he made a profit until he’d spent $11 million. He was going to hang in there one way or the other.

When did Benny step aside and you take the helm?

Every year a major wanted to buy us. I’d say, “Benny’s not in this for money, he’s in this for artist and staff dreams. Unless there’s a strategic partnership, he won’t sell.” In 2016, Roc Nation called. I said, “I gave them the speech.” A couple days later he said, “Would you come into my office?” I thought, We’re doing well. We’ve got all kinds of success. I can’t imagine he’s going to fire me. He said, “My wife’s health is not good. Even though the team’s taking the lead with everything, if I don’t sell this company I’ll be coming in every day and not giving her the time she deserves.” He said, “I think it’s time. I want $100 million dollars to protect the staff for two years and the roster for a year. If you can find that, whoever you think is best.” I went to visit Roc Nation; culturally, I didn’t feel it was a great fit. I was intimidated by them. Sony had the first right of refusal; what they valued us at wasn’t $100 million.

BMG came. It’s when they were entering back into recorded music. I thought, “Don’t they do publishing, or are they a distributor?” I fell in love with everybody there. At the 11th hour, everybody was throwing money at us, significantly more than what BMG was offering, but BMG felt like the best fit to take the next step for our artists. The deal was closed in 2017; Benny stepped back.

Being independent, you signed artists outside the box. Is that a superpower or secret weapon?

If you’re painting outside the lines and couldn’t easily classify as a country act, if you want a label home, BBR gives you confidence: “These guys know how to do it and will fight for you.” We’ve had success with acts that aren’t obvious; our partners trust us. No greater example than Jelly Roll. Most of that credit’s Jelly telling his story. We are now the home of “If I don’t fit in a box, I’m going to see if they’re interested.” There’s a cast of characters that comes walking through the doors now because they feel, “That’s a home I could succeed in. Those are people that will appreciate my quirkiness.”

Jelly said, “BBR is like a halfway house for artists and everybody’s successful, so I felt comfortable there. Nobody was going to judge me.”

You play into those things. Somebody else would’ve put Lainey Wilson in a push-up bra, or said to Dustin Lynch, “Do you have to be such a cowboy?”

I love those examples. People thinking about things outside the lines that we’ve done, they’re thinking things that aren’t organically country. When Dustin Lynch came out, the genre was pop-leaning, polished, and we came with this four-minute ballad with a guy in a cowboy hat. I heard, “That’s like grandpa. All the country acts now have baseball caps; there’s too much steel. You’re going to start with that?” I said yes.

Lainey, same thing. Female acts were pop-leaning, beautiful but had a glamour bent. Several people thought, “She’s too country for this genre.” People forget that was a disadvantage.

You flipped it.

You can be different, but if the artistry isn’t there, if you don’t have a strong identity, none of it matters. We’re not looking for the next whoever. We want the originals. I’m trying to look and say, “Sonically and thematically, where’s the genre right now?” If that’s identifiable, we don’t need to play there. We need to look forward. It might be a Jelly Roll, but something organic and stripped down.

You kept the growth slow and steady.

When things get too hot too fast, it doesn’t end in a great place—and it’s not a long-term sustainable career. It was calculated. There were many opportunities we didn’t feel ready for. It’s the artist-first mentality. I trust Jelly. Whenever we’re at a crossroads or if we’re in disagreement, I follow him and we win.

Beyond empowering artists, what are your strengths? Where do your teams excel?

I’m a mad scientist. I’ve always been smaller in stature, so you start at a disadvantage. I want to prove people wrong the right way, so I take more risks.

Other places have that tight family culture, but our staff has something special. They look out for each other. They live and breathe it. JoJamie and I hired people with hearts like ours. Mark Logsdon is a perfect example. Looking for that VP of publicity, a number of people talked about his heart. If you’re dreaming, taking care of each other and your partners, success will follow. Get up, suit up and do the right thing in actions, not words.

(The 2024 edition of Rainmakers will be published this fall.)