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A
Did Jake Owen discover you?
B
Yeah, I was playing at a barn for a wedding party thing, and Jake just happened to show up and watched me for a while, and I was like, you should go after this. Like, he thought I already had a deal. Right, right. I was like, no. And so he was like, well, I think you should reevaluate. I said, I'll tell you what, you take me on the road, we'll see what happens. He called me a few nights later and said, hey, we got a gotta run down to Florida. We're doing these three shows. I want you to come with me, open for me. I was like, all right. And so I went to my boss at work. His name was Harry. Harry was a good guy. I walked in, talked to Harry. I said, this is what's up. I gotta do this. And he goes, you'd be crazy not to try. He said, if it doesn't work out, come on back. We got your spot.
A
Welcome back to on the bus with Troy Ballhoffer. We have Larry Fleet joining us today. Larry went from working blue collar jobs to writing to performing bluegrass music for a living. He's continued to work at his craft as a singer songwriter and has written country music ballads like earn it and working hard that honor his roots. Please welcome Larry Fleet to the show. Hi, Larry.
B
Good to see you.
A
So here we are in Twin Lakes, Wisconsin, Country Thunder. And these fans are crazy here. This is your, like, fourth time playing the. Playing country thunder in Wisconsin?
B
Yeah, I think so.
A
Right.
B
Done it quite a few times. It's hard to keep up anymore, but, yeah, it's always fun and people always have a good time. They're very friendly, and they love good country music.
A
Let's start off like how you started where you're from.
B
Well, me and my guitar player, we're both from the Nashville area. We always kind of say we're the unicorns, you know, like, that rarely happens, you know.
A
Yeah, for sure.
B
But we have a few. Couple other boys that are from the area. But yeah, I grew up in, so White Bluff, Tennessee, used to be 30 minutes now traffic's worse. But growing up, it was 30 minutes from Nashville. People talk about, you know, the one red light town. We literally had one red light. And it was a big deal whenever I was in middle school because we got a McDonald's. It was a big deal. Grew up loving bluegrass music, and so I would pick around and do gospel stuff after church, and the family would kind of play, and it was just something fun to do. I never really knew that we could Make a living at it, you know? So my dad would say, hey, if you learn a skill in life, then you'll always have a job. So I learned how to do concrete and masonry work and thought that's what I would do. And then one day, I played a bar and made tip money, you know, in the tip jar. I was like, whoa, there's money here, you know, like, what is this? You know? And so it become a thing where I loved it. It was something I love to do. I never thought I could make a living doing something I love to do. Not a lot of people do. So it's a thing that has evolved and took a long, long time to really work on my craft. And when I was kind of coming up in it, it was a little different. You know, you didn't really have the tiktoks and everything. It was. You went and played bars and develop a drinking habit, and, you know, it's like you would do these steps that everybody did. And that's kind of how the music started for me, because it was fun. And honestly, like, I was a shy kid, so it gave me confidence when I would get on the stage, and people were like, wow, you're really good.
A
Just so our listeners are aware of the path. So you started playing live first and then started writing your own stuff.
B
I started writing music in high school because I was tired of playing other people's songs. Sure. And when you're in high school, you're going through a lot of things, and so you think you're in love, you know, with the first girl you meet. And so, you know, you're writing heartbreak songs when you get heartbroken, know, 17 or whatever. And so I was writing those songs and always loved poetry and things, which may not have been the most manly thing, but I like making things rhyme, you know, so that's where it started. But it was more poetry than it was writing songs. And I was just bored playing whatever song I was hearing. That's how songwriting began for me, was out of boredom of playing other people's songs. Once, you know, I started playing the shows, you had to play the COVID songs to. Yeah, give the people the bar what they wanted. But I would sneak in one every now and then just to see if anybody know, you know, you had some good ones, you had some bad ones.
A
Growing up in the non TikTok world, playing bars where buddies are smoking and having beers or whatever, and you got to earn their. Their interest, and that's the art of performing that you find it probably a lot Easier performing than a lot of these kids who didn't have that experience.
B
Yeah, for sure. And I've talked to some of the guys that got big on the tick tock or whatever platform. They never played a real show.
A
Right.
B
You know, they'd only played in their bedroom or whatever. A lot of them have never played a real show. I said, you go out, you're having to build a band, you're having to learn how to play with a band, you know. And now I learned in smoky bars where you had some wedges on the stage and everything was loud and feeding back. I used to run my own sound. So a lot of kids, they miss a lot of that. All the steps, they kind of skip by it and then they just end up on the big stage. And I'm not mad at it. Mine was a different path, but I'm glad mine was the way it was because I built fans along the way and they keep coming to shows. And I'll say, well, how many people have been here to one of my shows before? Majority of the crowd has been to a show. And there's other people that have been to 5 or 10 or even 25 shows.
A
I know one of your influences, but tell me your influences. I see Waylon's one of your influences.
B
Well, I named my son Waylon, and so.
A
Oh, that's a killer.
B
That's a little for my little girl, Stella. We had a girl come to the Green Room in Ohio, I think it was, and tattooed the whole band in the green room. Yeah.
A
That's awesome.
B
My influence for sure was Waylon. I named my son after him. My little boy's a total Waylon. Meet him. Like his attitude, like his whole thing.
A
Oh, yeah, he is, dude. I love it.
B
He's got a big heart and he's a very kind kid, but he's also. He does his things his own way. You know, a lot of people said, well, you know, it was Waylon Jennings and Johnny Cash. Well, I mean, yeah, that was influences for me. But I had an Allman Brothers cover band for a while. So, like, I was big into the southern rock, like the jam bands.
A
Yeah, yeah.
B
And I like to play. And, you know, not always do people want to hear a 12 minute song. Sure. But it's fun for a band to play.
A
All right. When you're rocking out right in the groove.
B
Yeah, absolutely. I learned bluegrass, I learned gospel, I learned Southern rock, I learned all of it. But I had influences in every different genre along the way. But songwriting wise, huge Willie Nelson fan.
A
You Played a gig with Willie, didn't you?
B
Quite a few, yeah. And he's.
A
That's pretty awesome.
B
Great guy.
A
Oh, yeah. I got a funny story for you.
B
Yeah.
A
So Country Thunder, Arizona. It's. It was scheduled over the ACM for whatever reason. I can't remember exactly the detail on it, but was. Kid Rock was headlining because none of the pop country guys could be there because of the acm. So it was rehearsal day. So Kid Rock, with direct support was Willie Nelson. So my emcees were Williams and Marie, who are legendary comedians in the country space. And they go, you gotta come meet Willie. So I go, willie's bus is parked right beside the stairs to the stage. I go on his bus and it's just. It's just smoke. It's weed, right? But he's got this thing hanging there, and it's his, you know, the mask he puts over, you know, to get his. Get his head. Get his hit of weed. But he stands up and. I mean, Willie is so much bigger on stage. His Persona is so massive, but he's really like this tall, right?
B
Very, very small man.
A
Small man, right? I was so freaked out, I said, man, it's a pleasure to meet you. He goes, I always like to meet the man who's going to pay the bills. And I said, it's really nice to meet you, Mr. Wilson. And he was so big that he didn't. Went right over his head. He had no idea that I called him Mr. Wilson.
B
Oh, man. The first time I shook his hand, I thought I broke. At this time, he's. He's in his later 80s, you know, when I was playing with him. So it's like, you know, he's a little frail at times, you know. So I went to shake his hand. I could hear it pop because I was excited, you know, you're a big man. Yeah. And I was like, oh, boy. And then he didn't say anything. And then the night I played with him, he said, I want you to come out and sing some gospel songs. I was like, yeah. And so he walks out. I thought, well, what are we gonna play? You know, like, I would at least like to know what I'm getting into.
A
Sure.
B
His band and crew, and they're like, ah, you'll figure it out. We didn't practice. There was no, you're going to stand here now. I just walked out and like, all right. And so he kind of kicked off into his song. They went into, like, I'll Fly Away or. Or Will the Circle Be Unbroken? So I'M kind of trying to sing more or less harmony with. With Willie, which is very hard. Yeah.
A
Cuz he's all over the place.
B
You don't never know what he's on tune. It's never the same. And so the first night I just kind of stuck back and then got a little comfortable as the tour went off. And then down two or three nights in, I thought I'm gonna go for it. He was singing like one or two, like one verse and then in the chorus and then into I'll fly away.
A
Right.
B
Well, I know all the other verses of. Well, the circle being broken. I thought, well, I'm gonna jump in there, it'd be fun. So he does his first verse and chorus and then he's kind of looking over and I just went into Undertaker, Undertaker. And I look and he just kind of like. And I thought, I'm the first person to probably ever piss off Willie Nelson, you know. And he kind of looked at me and I was like, oh no. Like I shouldn't have done that. And he was like, yeah. And I was like, he was in we're on. So I did it. And then afterwards the whole band was like, that was awesome, man, that was great. And I was like, it could have went terribly wrong, but I thought it did for a minute. But he such a. Just a kind man that he just, he knew I was excited.
A
I mean, that band is amazing.
B
Well, they've been playing together for 100 years and that's what I said coming in. I was like, I want to, to have that kind of career. Yeah. Where you bring people in and they're with you for a lifetime. And so that's what I've done with my band. We've had one or two come and go, but for the most part, guys have been with me for 10 plus years, you know, and so. Which is a rare thing in, in the industry.
A
Oh yeah.
B
You kind of swap hands a lot, you know. But we've been able to keep the core group together.
A
So obviously you work a lot. How many dates a year are you doing now?
B
Anywhere from 90 to 100 around here. But we're doing Australia, we're doing Europe. I'm a worldwide sensation, you know what I mean? Ye, you're global.
A
I love it. Your fleet's global.
B
I never thought I'd fly on an airplane, you know what I mean?
A
Here we are. And so do you ever look in the mirror and go, man, this is pretty cool.
B
Yeah. When I got a record deal, I was pouring concrete for a living. And so my wife was with me before anything ever happened. She seen me in the bars, like, and was thinking, what are we doing here? You know? And then, hope that day job's fantastic. Yeah. And so I'm doing concrete. I'm playing the bars at night, and a couple of boys with me. We were doing that, and then it just worked one day. And then we went to Ace Hardware one time, and I. When it first started happening, a young boy come out. He said, hey, are you Larry Fleet? I said, yeah. My wife with me. He goes, can I take a picture with you? I said, sure. My wife's like, you want me to take it for you? He was like, yeah. And we got over there and he was shaking. He was so nervous. And I was like, and this is right when it starts working, you know, everything's starting to move. And then my wife gets in the jeep, she goes, he was shaking to meet you. I said, yeah, I wonder why. And she was like, I don't know, it's kind of crazy. And then it's like. It's happened plenty of times, you know, throughout the years, but that was one of the first times, like, you realize your fame. Yeah. Some people have no idea who I am, you know, A lot of people know, but for some people, I'm their favorite singer. And so I learned that too, that you are somebody's Willie Nelson, you know. And so whatever I do to make sure I'm doing it the right way.
A
So balancing the show business. Cause you have a kid?
B
Two of them. I got a little boy and a little girl.
A
It's gotta be hard to leave on.
B
It is. But, you know, I've been fortunate enough now that I've got my own bus and band's got their bus and everything, so I'm able to kind of do things that I couldn't do as a kid. And this industry and this job has provided a lot, so it's been nice to kind of give them that. But they love it. They love coming down the road. This week was summer camp, so they're not out with me this weekend, but. But yeah, they. It is very hard, especially going to Europe. They're too little to go to Europe really right now, and so I got to go for two weeks.
A
Have you played Europe before?
B
Yeah, Yeah. I was direct support for Morgan Wallen last year over there. We did a bunch of stuff. And then I went with Morgan once before to do a one off in London, and then last year we went back for direct with him. Me and Morgan been buddies for A while. And he. I think he knew that my music would do good over there. So when I did the thing with him in London and then went back the next year and I said, well, let's try doing my own thing in London. We sold it out in two weeks.
A
Wow.
B
And so it's kind of cool to see what music has done and the different avenues for music now and how, you know, it used to be if you couldn't get on the radio, then it was hard to build a career.
A
Yeah, you were done. I mean, you were stuck at one level. You know, either you're a bar act.
B
Or whatever, and now you have the stream and you have. YouTube is one of my biggest followers. Like, I got 350,000 subscribers or whatever it is. Every time we put a video out, it's going all over the world. My manager just called before I come in here and he said, hey, we're looking at Brazil. You have 20,000 fans in Brazil. Wow. And I was like, where's that at? Yeah, yeah, exactly. So you never know what it's going to do.
A
Everyone talks about, you know, you're not making the same money off the records that you used to make, so now you have to go out and work. But in saying that the ability to launch your own music is easier. You don't have to have a record deal anymore to have a record.
B
Right.
A
That the world can listen to. And I think that's really cool. And everyone's working a lot more live, which I think is more important than actually recording music. Touching the people, touching your fans, that's.
B
How you build a fan base. You don't want to blend in. You want to do your own thing, stand out. You want to stand out. You want to have a song that impacts somebody, you're right. You don't have to have that record deal anymore. Like, that was a big deal for me to get a record deal, and it helped me tremendously. Right. And a lot of people say, well, I'm independent.
A
I mean, at the end of the day, every artist wants a record deal.
B
It's in the plan, you know, 100%. And if you need development, which is what a record label is intended to do, and now it's changed a little bit. Where we need you to be viral on TikTok and then we can do something with that.
A
Yeah. They grind you for how many streams you're doing there, how many. How many moments you're having. Right.
B
Big Loud Record signed me. And so that was strictly off of nothing viral and nothing viral. They Said, here's some talent. He's got good songs, he knows who he is, he's got it all together. Sure, we just need an audience. So they come in, they were able to help me build a record and put money behind me to get me out in front of the people so that I could get my brand out. And there's a lot of people claiming they're independent and that that is true. But anybody that's really, really big and they're independent, they have a whole team behind them to get them to that, that spot. So I learned that. And it was a weird kind of move, moving from big loud to being independent. But then you realize all the other people that want to be involved with you, and then you do exactly what you want to do it, where you want to go to, how you want to do it. And so that's where I'm at right now. And it's an awesome feeling to know I'm in control of everything. You put songs out, real people come to the show. I think Willie Nelson did it, right?
A
I mean, he never stopped touring.
B
No, he's still doing, still doing it. And I watched it the first night. I said, there's a seven year old little girl and there's a 90 year old woman in a wheelchair. They're all in a Willie Nelson show. He's got every demographic. And I was like, I want that. Yeah, that's kind of what I've tried to model myself after. So the sudden bottle rocket burst to the top most of the time, doesn't last very long.
A
I agree.
B
And so I want to go the little slower route, which my wife is like, I wish it'd speed up a little bit, you know, but it's, you know, your trajectory is, is heading up and that's what you want.
A
Got a fun fact question for you. Who's your favorite rock artist?
B
Greg Allman, you know, with Almond Brothers. But you know, there's the Hendrix and there's all this Steve Reval, but mine's Warren Haynes because I think the man is a one of the most soulful, has one of the best tones.
A
Cletus. Cletus T. John.
B
So I own some burger restaurants now.
A
Oh, fantastic.
B
I was in Nashville one day and this guy said, asked me if I would come by and check out his restaurants. I did. So we went and had a burger. It was awesome. And he's like, would you like to be a part of this company? I said, yeah, for sure. Yeah. You got a burger like that, I'm in, you know, so I bought into the company. I'm a small partner. And it started kind of downtown, Elm Hill pike in Nashville there. And it was a little hole in the wall block building, only open for lunch. And then we just opened up a new location in Bellevue West. West Nashville. It's a lot bigger and it's really cool. It's kind of 80s 90s themed. You know, it's kind of like arcade games. But it just got voted, like, the best burger in town by 1100 people or something. Whatever. It was like, they did it.
A
I go check it out.
B
It's great. But Shane, the guy who started the company, Cletus was his granddad's name. And what they do is once a month we go downtown to, you know, Nashville, like by the riverfront area right there, and we'll feed the homeless. So we just bring out grills. I went one night, I made 300 hamburgers.
A
Really?
B
Yes. I mean, that was all the burgers.
A
Pretty rewarding, isn't it?
B
It was great. Yeah. I just sit on that grill. We just bring Blackstones out. Yeah. So we made 300 hamburgers, what we brought. And there were still people lined up. So I was like, well, what else we got? So we had cheese. And I said, well, now we're doing grilled cheese. So, you know, we're making whatever. We're just feeding as many people as we could feed. So, man, that's pretty cool thing to give back to. And I think that's important. Whatever you do, if you can make money at it, you should try to get back on something.
A
I'm going to check it out.
B
Yeah.
A
When I get back to natural, finally.
B
Well, and Luke Combs lives down the road there, too. It's his new favorite bur joint. And then Jake Owen went the other day, and he was talking to my.
A
Did Jake Owen discover you?
B
Yeah. I was planning a barn for a wedding party thing, and Jake just happened to show up and watch me for a while playing Merle Haggard songs or whatever, you know, and talked to me afterwards. He's like, you should. You should go after this. Like, he thought I already had a deal.
A
Right, right.
B
And was like, no, I pour concrete for a living. You know, I'm just doing this for some dude paid me like 400 bucks, you know, and so he was like, well, I think you should reevaluate. So he gave me his number. He said, let's talk. So we exchanged numbers. Next day, we talked. He was like, I think you should quit your job. I was like, well, I don't know. We'll see. So he invited me over to his house. We hung out all night, and come on, you need to quit your job. You need to quit your job. I said, I'll tell you what, you take me on the road, we'll see what happens. He called me a few nights later and said, hey, we gotta run down to Florida. We do these three shows. I want you to come with me, open for me. I was like, all right. He goes, you just ride my bus. So talked to my wife, and she was like, I think you ought to do it, you know? And so I went to my boss at work. His name was Harry. He's like, man, that's really cool. Like, go for it. I said, okay, I'll need off for a couple days. So I left and went on the road. We were coming back home. He's like, we got Canada next week. You coming? I was like, sure. He was like, you gonna quit your job? I said, well, I would like to give him a notice, but yeah, I guess so. So I walked in, talked to Harry. I said, this is what's up. I got to do this. He goes, you'd be crazy not to try. Absolutely. Go for it. He said, if it doesn't work out, come on back. We got your spot. It was a nice thing because you.
A
Had full support from your employer.
B
Yeah.
A
Unheard of.
B
Yeah, I know. Yeah. Like. But it was a big risk, too. Sure. And so for that first two years, I didn't hardly make any money. Right. Even when I got a record deal, I was one of the brokest I've ever been.
A
Because you weren't working? No, we weren't slinging concrete.
B
And I want to say, like, my first deal was, like, they signed me and it was like a 50 grand advance, and it lasted for two years, which is not enough to pay bills.
A
It's poverty.
B
Yeah, it is. And so I was touring. I was not making money. I got this deal with Winnebago, and they said, we want to help you out. They heard my song, Working Man. I was like, that is our brand. We're going to give you this 40 foot Winnebago. So, a little bit shorter than a regular tour bus, but not by like five foot.
A
Yeah, yeah.
B
I was like, okay. I never drove one of those, but I was like, I can figure it out. So I drove up to North Carolina, picked up a Winnebago, and I called my van and I was like, we're on the road now, boys. And so we loaded up and never looked back. I drove that Winnebago for years. We put thousands and thousands of miles, but I was making 500 to $1,000 a night. I made enough to pay my band. Yeah. And I hope that I sold a few koozies and T shirt. First few years I didn't make any money at all. It went back into my company to help me get going and then make sure that everybody was paid.
A
Well, Larry Fleet, it sounds like you've had an amazing ride.
B
It's been wild.
A
You got many years ahead of you.
B
Yeah, I hope so. Yeah.
A
And I wish you the best, man, because your story is amazing. And that was a awesome interview. Thank you very much, my friend.
B
Thank you.
A
We're back for another installment of On Tour with Troy, where I answer questions from you, the fans. Well, they start very early, about 7am in the morning, 86am when the first trucks start coming in, when the artists of the evening. And they end at about 2:00 clock or 3:00 clock in the morning. So they're long days, but the best days of the life. And some are challenging when you have weather and some are just absolutely amazing like today. And that's a typical day in Country Thunder. Well, we had ZZ Top playing Country Thunder one year. The sound mixer had pushed the PA system to an enormous amount of volume. It was over 110, 115dB at the back of the venue. So the actual mix position is about 125dB. And the PA went on fire in the midst of the show. So the riggers had to run up there and put the fire out and the the middle of the show and the band kept playing. And that was a pretty big mishap. But everything worked out perfectly fine. And with amazing crew that we have at Country Thunder, they were able to contain it. And the show continued on without probably a lot of people understanding what actually happened.
B
Stuff.
A
It was great. Cheers to the crew captain Fantastic and the Brown Dirt Cowboy, Elton John, which I think is one of the greatest records and transitional records from rock pop artist to the country kind of influences that he had. I think it's a great record. Him and Bernie Coppin wrote that record and I just love it. And that's my early morning wake up record when I'm just chilling. So the weirdest thing that has been asked in the contract were candles that could only be found outside of America, that were a must and have to be. So we imported them and wines from France that are over $1,000 a bottle. Rothschild Lafitte had a couple of those on Riders before that we had to contract or that we had to supply within the contract, which were very difficult to get at the time. Those are kind of the more weirder things that I've seen. I've not encountered the Brown M and M. That's about as extreme as it gets. If you have any questions about life on the road, leave us a comment at Country Thunder on Instagram, x YouTube or in the reviews, wherever you get your podcasts. Big thanks again to Larry Fleet for sitting down with us today just to listen to him playing his smoky bars and trying to earn the interest of the the patrons to getting a record deal opening for, I mean Willie Nelson. I mean, a legend. I mean what a great break. So he really has a true story of a troubadour and a country music artist that turns every stripe that he has on his shirt. Really looking forward to seeing Larry tonight. Please catch him on tour. He'll be out this fall. Thank you again. Troy Ballhoffer on the Bus. Be sure to follow Country Thunder on all our social platforms. CountryThunder. We have new episodes dropping bi monthly. Make sure to subscribe to the podcast so you know when the new episodes hit the feed.
B
Is this your bus?
A
Yes.
B
Yeah. Nice rig. You got a little star fleet in the back.
A
I'll check it out. It will absolutely.
Date: October 16, 2025
In this episode, Troy Vollhoffer, owner and founder of Country Thunder Music Festival, sits down with rising country artist Larry Fleet. They discuss Larry’s journey from blue-collar work to the big stage, the realities of building a career in country music, and the importance of authenticity and persistence. The conversation is candid and full of behind-the-scenes insights, highlighting Larry’s influences, his breakthrough moments, and the new opportunities for artists in today’s music industry.
| Timestamp | Speaker | Quote | |-----------|---------|-------| | 02:37 | Larry | “I never thought I could make a living doing something I love to do. Not a lot of people do.” | | 04:44 | Larry | “A lot of them have never played a real show… I learned in smoky bars, with wedges on the stage, everything loud and feeding back.” | | 07:50 | Larry | “The first time I shook his hand, I thought I broke… at this time, he’s in his late 80s.” (On meeting Willie Nelson) | | 08:58 | Larry | “I thought I’m the first person to probably ever piss off Willie Nelson, you know.” | | 10:26 | Larry | “Some people have no idea who I am…for some people, I’m their favorite singer. And so I learned that too, that you are somebody’s Willie Nelson.” | | 12:54 | Larry | “My manager…said, ‘Hey, we’re looking at Brazil. You have 20,000 fans in Brazil.’” | | 14:18 | Larry | “Big Loud Records signed me…off of nothing viral… just talent and good songs.” | | 19:18 | Larry/Boss | “'I gotta do this.' He goes, 'You’d be crazy not to try…if it doesn’t work out, come on back.'” | | 19:37 | Larry | “My first deal was…a 50 grand advance, and it lasted for two years, which is not enough to pay bills.” |
Larry Fleet gives listeners a refreshingly honest look at what it takes to succeed in country music today—persistence, humility, and a willingness to start over. His unique blend of traditional influences, modern hustle, and down-to-earth attitude sets him apart, making this episode a treasure trove for aspiring artists and fans alike.
Memorable closing:
“Some people have no idea who I am…for some people, I’m their favorite singer. And so I learned that too, that you are somebody’s Willie Nelson.” – Larry Fleet (10:26)