The most important thing I can do as a business person, as a musician, is to super serve my core fan base. To sort of over-deliver what they love about what we do from a touring and from a recording perspective. If we can super serve that core fan base, they stay with us forever. Do you know who the heavy users are in your business and do you know why they matter? Welcome to How Leaders Lead. I'm David Novak and every week I have conversations with the very best leaders in the world to help you become the best leader that you can be. My guest today is Drew Holcomb. He fronts a beloved Americana band called Drew Holcomb and the Neighbors and their music has been featured on over 150 TV shows including Grey's Anatomy and Parenthood. His music has also been featured in My Life. I absolutely love his band and I can't wait for you to get a glimpse into how Drew leads both in his music and the business behind it. Drew knows something that a lot of leaders don't. You can waste a lot of time and a lot of energy chasing after customers and fans that won't really impact your business in a big way. If you want to start 2025 with more focus and efficiency, this conversation is going to help you do it. Plus, it packs a real punch of creative inspiration. So here's my conversation with my good friend and soon to be yours, Drew Hol comb. Drew, it's so great to have you on the show. It's really great to be on the show. A big fan of the show. Listen to it all the time. And a big fan of you. So looking forward to this. Well, I'm a big fan of yours because we played golf a few weeks ago and you made like a 20 foot putt. We win the match and I felt like I won the Masters with you big guy. That was a big punchy band. That was a lot of fun. You're fun to play with. I love your competitive spirit. It leaks out onto me, which is fun. We're going to have some fun with this podcast. I learned that you post unsolicited advice videos fairly often. So let's hear one of them. Give me some unsolicited advice. Well, they often sometimes they have a lot to do with travel. I travel all the time. So I post these videos about how to properly exit an airplane, teaching people that, hey, everybody wants to get off this airplane. Please wait for the people in front of you and be ready. Have your bags ready. But I also have unsolicited advice about sort of funny things like one of the first ones I ever posted was don't fish upstream of Sam Holcomb or you might get hooked in the penis. Which is a true story. About a... Sam, is that your brother? That's my younger brother. Yeah, he, you were fishing one time growing up his kids and sure enough, I got hooked through the pants right in the picker. But it was just a, it was sort of a, you know, I'll be honest. When Instagram started doing the reels and that was a new thing for them and they came to a bunch of people like myself, musicians, you know, artists, etc. and said, "Hey, we're trying to get people to do this." So we all do it and they said, "Well, you know, we'll pay you some money to make like 30 of these." And I'm honestly a bit of a Luddite. I'm not super technologically savvy. And so I didn't want to have to learn how to edit them. So I said, "Can I just make these one-off unsolicited advice videos?" And so I came up with 30 of these things and put them out over the course of time and they've become sort of a calling card and it's a way that I've learned to both share my grievances with the world and also my funniest stories. I love it, you know. And I can't wait to get into how you lead you because you are a great leader. People are inspired by you. And, but I want to take you back. What's the story from your childhood that shaped the kind of leader you are today? I was very influenced by my father and my grandfather. I grew up five doors down the street from my grandfather and he's my mom's dad. And he just included me in everything and he taught me a lot of curiosity. So I went hunting with him probably 30 times in my life. I went fishing with him probably 20 times in my life. I played golf with him a number of times. And what I learned from him was that character is something that you can pick up on by spending a lot of time with people. You know, that character is mostly taught through spending time with people and watching them live their lives. It's not something you can read about character in a book, but you experience character when you see how somebody that you respect treats someone or you learn what what where character is not when you spend time with somebody and learn how they treat people in a poor way. And so my grandfather always treated everybody no matter their station in life with a lot of kindness and with a lot of value. And whether that was, you know, stopping at the place to buy crickets on the way to the morning fishing or, you know, how he treated caddies. And then he was a, he was a retired surgeon. And so he, he, he lived a very interesting life. And then my father was it was one of the biggest memories I had in my life was I was a sophomore in high school and I had written a song with a friend. It's probably the first song I ever wrote. And we were playing it at the talent show. And what I didn't know was that he had gotten a call that morning unrelated from my math teacher about how disrespectful I had been that week in class. So I get up there and I play this song. I'm very excited about it. And it's my first song I've ever written. And I get in the car with him afterwards. Like I said, I'm 15. I get in the car and we're driving home and I'm waiting on him to say something about this song. I just performed in front of the whole school. And so what do you think about the song? And he said, we'll talk about the song later. We have another conversation to have about a conversation with your math teacher I had today. No son of mine will get a call about being disrespectful to his teacher. We'll get back to your music. But none of that matters if your, you know, if your character's not there. And so those were two sort of anchor and you know, rudder realities for me growing up was that I had strong leadership in my sort of development as a human before I before I had any sort of idea of what my calling in life was going to be. You know, I've read where you described your dad, HAMP as a dream encourager. You know, what kind of influence did he have on your career? I think more than anything, he just gave me permission to try a lot of different things. I was a very curious kid. I was pretty, pretty bookish in a lot of ways, but also was like an okay athlete and I was interested in, you know, I did the scouts and I played some sports and I was in some play. Like just kind of played with everything and he gave me a guitar when I was young. I think his father had discouraged music his father in the early 60s considered in early 60s and early 70s had considered it, you know, sort of like , you know, something that the hippies do and he discouraged him from from doing that. And so I think he had some, some wounds from that and wanted to sort of write that and his story as a father. So he bought me a guitar when I was young and encouraged me to learn how to play. He basically said, look, if you work hard and you treat people well, I don't care what you do with your life. When I told him I wanted to do music we most of the people that in my life were pretty surprised that I chose music I think they thought that I was headed towards a more sort of standard career path of, you know, corporate world or lawyer or something along those lines. So everybody, you know, they knew I liked music but it wasn't, I wasn't that kid that sat and played songs all the time and growing up I had other interests and other hobbies as well. And so I decided to give music ago I wanted to make sure and kind of get his blessing on it so I took him to get coffee and he said, I said, dad, I just graduated and I said dad I think I want to give this music thing a try. I want to want to give it a go. And he just asked me said you're going to work hard at it and I said, yes, sir, I am. He said, well, this is a really, really hard business. If you promise me you'll work hard at it. I'm in your corner. And he said and also if you promise me that if you know it's not going to work that you'll be honest with yourself and move on to something else. And I said, I'll make the promise to you and he said alright great let's go, let's go to the guitar shop. And I said, I want to give you a 3500 awesome guitar. And so that evening I told my mother the same thing, you know, I want to go be a musician. And she said, well, you make me one promise. I said, yes, she goes just promise me that I can always understand the lyrics. And I said, no one ever gets through that. And I said, no one ever gets through that. And I said, yes, no one ever gets through that. And I said, yes, no one ever gets through that. And I said, no one ever gets through that. And I said, no one ever gets through that. And I said, no one ever gets through that. And I said, no one ever gets through that. Yeah, yeah, well, I went to University of Tennessee and when I was applying to college, I was looking at a lot of different spots and Peyton had graduated, I guess he graduated 98 or 99. I can't remember 98. And when he left, he endowed a leadership scholarship. Obviously it was not an athletic scholarship because I'm not, it was not any sort of great high school athlete. But I interviewed for the scholarship and I, and I, there's only one recipient and I was lucky enough to get that scholarship. And so basically, I went to University of Tennessee, not only for free, they covered everything room, board books, travel, stipend, and then you had to study abroad, which was really great. And to his credit, he stayed in touch with me and a lot of the other recipients through the years. And as I started doing music and touring, he would every once in a while have a note sent my way and, and then, you know, fast forward 15, 20 years when my career was really taken off, we actually became friends and but yeah, it was a really, it was a great start to my college career to be able to go into college with no sort of financial obligations but with a hefty weight on my shoulder to sort of live up to the expectations put on me. So you got a leadership scholar scholarship, you know, people always put you in that category. Yeah, I think so. I, I, you know, I was a classic leadership kid in high school I was like present student body and Eagle Scout and, you know, sort of checked a lot of those boxes when I was young. But I also, I always had this personality trait, where if I had an issue with somebody or a problem with somebody, I would go straight to the source and just talk it out, you know. Now when I was young that that had, it was a little more brash and then it is now I think I've learned how to do that well and with kindness and sort of the velvet hammer, if you will, but never been a, just never had a lot of fear and always was quick to help people make make, make, make decisions and so even jumping into a music career was like a lot of people who have talent sort of wait around for someone to tell them to, to give it a go and I just thought to my I didn't really wait on anybody said I love this I'm going to give it a try. And so it's a different sort of formal leadership obviously I mean I do lead a team I've got band and crew and all these things but there's a lot more emotional leadership in music than there is sort of, you know, nuts and bolts. You know, your band is called Drew Holcomb in the neighbors and you've been playing music together for 20 years or so and what's the key to making working relationships last as long as yours have. Yeah, you know the music business is very interesting because a lot of what people hear on the radio and what they hear on records. Most artists don't use their touring bands for their recording. They use these, you know, studio players these really professional guys and I remember I just started playing with sort of a consistent group of guys, the neighbors. And I was like, this is, you know, 20 years ago. And I was going to go and make my first record and the producer said okay we needed to hire a band and I was like well I didn't I didn't understand all this is what do you mean hire a band I have a band. You know, and he said, well no no you're going to use these professionals they 're better it's quicker we'll get it done and I'm like yeah but these are these are my guys. I want these guys to play on my music they helped me arrange it and they have sort of bought into it already. And we'll give them a try we'll get in the studio see if they're going to see if they're good enough and they were all pretty young I mean Nathan was 21 rich was 22. I was only 24 and recording the studio is much different than playing live because there's this there's a sort of as close to you can get his perfection is sort of required in the studio versus much looser less perfection is is necessary on the road. And I went to me and he said oh you know these guys are pretty good. So I fought for them early. I fought for them when they were when they were really young and gave them ownership and then practically this is another thing that most artists don't do I gave my band points on the record meaning I gave them permanent artists. And so I just I think I invited them to the table creatively and I invited them to the creative to the table economically in a way that most song writer artists don't do. And that has I think created a nice loyalty we've now been on the stage together some of us for 20 plus years. So everyone it's cool. We'll get back to the interview and just a second before we do though have a question for you. Have you downloaded the how leaders lead app on your iPhone. If you haven't take 20 seconds right now go to the app store search for how leaders lead and download the how leaders lead app in the app every day you'll get a two minute video. So go to the app store search how leaders lead download the how leaders lead app and start your day every day with two minutes of leadership wisdom it'll take 20 seconds go to the app store download the app and you'll be able to watch every day just like me the leadership insight from how leaders lead. I want to go back to what you said earlier I thought it was interesting you said that you kind of specialized in emotional leadership versus the nuts and bolts leadership. Draw the differentiation for me. I think music is so so magical because a couple things one it's soundtracks people's best and worst moments. When you graduate in high school and you're driving around town with your friends and you listen to music those songs that are on the radio at that air in your life are permanently etched into your story. When you fall in love when you have your first heartbreak when you get married you have your first dance you have your father daughter dance like there's all these little moments of life that are sound tracked by music and so that's sort of to me it's sort of the back drop music gives people emotional language for their best and worst moments right and so you're trying to help people and example I'll give when I started thinking about making music I went to a personal tragedy I lost a brother when I was in high school and all of the sort of philosophical religious language that people were trying to encourage me with about that experience didn't connect nearly as much as the music did. Music was what gave me a frame for my grief and that's the moment where I went man I would love to be able to do this for other people someday and just kind of planted a seed in me. So, the songwriter your job is to try to give people a language that they may not have on their own for their own experiences and so you can do that in a way that challenges people to be a better version of themselves or that and so lots of different songs of mine the song like another man's shoes for instance is a is a there's a bit of a call to action to people to take a deep breath and to remember that the people that they interact with on a daily basis whether they know them or not are also humans with their own story and care And music did that for me it sort of gave me language for my own life and so I think that's sort of the emotional leadership part of music making that's different than, hey, you know, this is your team this is your job and so my actual like business team is probably less than 30 people, but I have 55 million people listening to my music in and out of different years, you know, and I only get three minutes with them, but a lot of times that three minutes can be really important. Yeah, your music has been very, very important to me in my life I can tell you that for sure. And I've heard you say that your music does not belong to you. Explain. I was, I got into an argument with a friend who's a self starter he started his own law practice, and, and he, he was saying, you know, really at the end of the day, it's those those of us who are entrepreneurs that took the chance that we're responsible for all this stuff. And I was like, man, I could not disagree with you more, like, you know, and that that was, I said that to him and we had this long argument so I got to thinking about this idea that the creative act is a shared act, the act of I sort of think about music and three as a play of a three act play so the first act is the songwriting. And I remember the idea percolates a lot of times for me it either happens alone or maybe with one or two other people, but also in that room are the ghosts of all the music that I've listened to my entire life, you know, and the guitar maker and his creative energy, and, and then this the second part which is the most collaborative for me is the recording of that song and so for us what we do is we get five or six musicians in a room in a studio we also have a sound engineer and a producer, and typically a runner who's like a young kid who wants to get involved in the industry. All making this process happen in real time and there's this collaborative piece and so not only are the, and then you have all the ghosts of all the music that that broader eight people have listened to their whole lives and their knowledge, and their teachers from college and the, and for me I wrote a song maybe I wrote a song about, you know, from a book that I just read and the creative energy that took to write that book, and then all the equipment in the studio, the architect who built the studio that makes it sound great the designer of the drums, the builder of the drums. There is so much creative life that's happened in these different processes, and then the third act is where you then take that recorded thing, put it out and go play a live show and experience that and the same thing happens with the live show you have the security guard, the sound guy, the person who designed that building, the dream of, you know, creative creation involves so many people that are tangential and, you know, direct and indirectly influencing that creative expression and then the experience of it live, the experience of it on record. I basically just did a TED talk about how dreams don't belong to you put them out there into the world and then, and then they also get interpreted in ways that maybe you didn't know. They would be and, and I think that's a beautiful thing about creativity is that it, it's alive it's vibrant, it changes. And I think that's a really that idea I think is sort of translatable transfer able to almost anything, you know, it's sort of a little bit of a stance against the great man idea that, well I do think it does take somebody with the courage to sort of lead the charge, leadership in and of itself as a collaborative experience. And I think that's true in the creative space as well and I think so many creative people tend to think of, you know, music making or fiction writing or acting as these sort of the sort of great man, great woman idea and I still think that's very collaborative. You know, I listened to your TED talk, Drew, it was a great TED talk. I mean, you know, I love a lot of them, this is a really good one. You talk about a dream being both a guide and a gift. Can you share a pivotal moment in your life when holding on to a dream helped you navigate some uncertainty or challenges because, you know, people can chip away at your dream a lot. Yeah, yeah, there's a lot of external forces on dreams, you know there's there 's oftentimes this economic, you know, and then criticism, both legitimate and illegitimate criticism of your work. And then sometimes your great ideas just don't connect with an audience like like you expect them to. And so there's there's these external forces I'll never forget. We probably got sixth record was a record called souvenir. And at this point, I started making records in 2004 and so fast forward to 2017 so I'm 13 years into this career. It has far surpassed all of my dreams of my expectations of it. And I'm really living a dream, but it had also become a business. It had become full of stress . It had become full of financial obligations. It had become full of creative expectations that were sometimes on that. So anyways, I put this record out called souvenir that I really loved and worked really hard on. But no one cared like for the first time in our career, our trajectory sort of went from this constant steady, you know, growth to just less than a plateau. It was like, it was, it was turning the opposite was turning downhill. And I built out the tour expenses, expecting growth. And but we weren't, we weren't selling more tickets. And so I was losing money on the tour. The record wasn't selling and I was in a financial pickle. And, and then also creatively was feeling very sort of outside of myself because no one cared about this music for the first time. And I realized how much of my identity was held up in that. And I, you know, just wasn't in a good spot. Had a little break on the tour. And I go play golf with Vince Gill. And he says, you know, Drew, how are you doing? You know, and he's, you know, legendary artist made a million records and, you know, won a pile of Grammys and this and that. And I tell him, I say, you know, honestly, I'm not doing great. Put out this record and it's just really tough. Nobody seems to care and it's just kind of weird. We've always had this growth and now it's not happening. I'm just kind of wondering if it's like, if this is the beginning of the end and he started laughing, he goes, no, no, no, just go make another record. And it was such a, it was such a light bulb moment for me where I was letting so much of my own history and my own story and my own expectations. Tell me that this thing was almost over. And he just was like, no, it's not over. That's ridiculous. Just go make another record. Hey, Drew, if you ever had an idea that was so big that it just scared the hell out of you. I mean, you know, you talk about, you know, one of your flops, but how about, did you ever have an idea where you go, oh my God, this is like magic? Well, we had this idea of starting a music festival 10 years ago that my poor managers were, you know, I knew that I was telling them about it and they're looking at me like, I can't believe you're going to ask us to do this with you. But they're also a bit of, you know, dreamers as well. And so we started, I mean, with nothing, no financial partners, just with a couple of sponsors and through this festival in Memphis. And ended up doing it for a couple of years there and then moved it to Chattanooga, took on a partner and it grew to be a poll star, which is like the , you know, the big music business sort of business magazine, touring magazine ranked it the best small market festival in the country within six years of us starting this thing. And it's just a wild hair idea. We had no idea what it would grow into and what it would become. And it was, you know, there was definitely some foolishness involved in it, but I like a good, a good foolish challenge. My wife laughs though she's she gets a little, I mean obviously I travel a lot for work, but she gets a little nervous when I'm home too much, because if I'm home for, you know, more than a couple weeks at a time, she's afraid she knows that I'm going to come up with some other dream because that's just what happens, you know, and I'm a bit of a bit of a bit of a dreamer and I'm okay with that. That's funny, you know, I used to say the same thing, the worst thing had happened if I get a day by myself. I come up with ideas that were way ahead of where we needed to go, you know, and move on to something else versus focus on what we really needed to get done. And then your business songs of the engine that make the whole thing go, you know, how do you cultivate your own creativity. Yeah, yeah, it's changed over time. When I was young, it was very much a sort of weight for inspiration, sort of model where I would write very intentionally and I was just kind of, you know, get into a zone and write every day for a little while and there's a hunger that drives that I think both hunger to prove yourself, but also a financial necessity of man, if I don't make this work, I'm going to have to get a real job, you know, as you know, a lot of musicians, all of us are sort of really, really, really trying hard not to get a real job. You know, I think that's what Warren Buffett, I think Warren Buffett looks at his job the same way, you know, he says he tapped answers to work, you know, because he loves what he does, you know. But, you know, one of the things that really strikes me about your songs is that the lyrics are simple and at the same time very complex. I mean, use words in your songs that you'd never hear in any song. You know, it 's kind of surprising. If you haven't listened to Drew Hokem, listen to Drew H okem, and you'll know exactly what I'm talking about. Do you have a process you used to define these words that help you with your lyrics? Yeah, I do. I have journals sort of strewn throughout my writing space here in my office. What I do sometimes is I'll go buy an actual physical newspaper, New York Times , Wall Street Journal, whatever, and just go word hunting. So I'm not even necessarily reading articles, I'm just looking for words so, or less the sad. I'm just going to go to the book of poetry here. Okay, let's see. Okay, celebrate and I'll write that down. Soul, write that down blood, write that down. Overhead, wind, silence, and then I'll go back. And for every word I'll find myself find five or six words that rhyme with that word. So I have a song called American Beauty. I had the word, "Canyon Companion." And so then I had this little riff. I got a little guitar here. Why not just pull it out? So it's like, okay, she was a good companion. She was a good companion. Okay, that's cool. I was like the Grand Canyon. And they're like, oh, that's kind of cool. You know, so what I always say is that the enemy of creativity for me is an empty page. I never start a creative project just looking at a blank page. I have this, these journals full of words and ideas and I have a voice memo full of musical ideas. So I just make myself sit down and play guitar and just practice and play and play and play all the time. Like you said, tap dance and work. If I see a guitar, just want to play it. It's like, you just got to put my hands on it. So I have this well of musical ideas and then lyrical ideas. They're always just sitting there waiting to be married together and into a song. [BLANK_AUDIO] [BLANK_AUDIO] [BLANK_AUDIO] [BLANK_AUDIO] I wrote a song earlier this week with a guy, a country songwriter named Larry Fleet that I really like. And I just had this, one of the things about journal, the phrase, "seat at the table." And so we wrote a song about it. Everybody wants to have a seat at the table. Everybody wants a piece of the pie. And there's just, there's sort of a never ending supply of creative ideas out there. But at this point in my life, I have to block the time and force myself to get away from kids and life and financial responsibilities and get away from the golf course and get back into the studio and write. And I still love that writing piece, but it also still scares the hell out of me every time, because it's hard. Sometimes you sit down to write and you come up with nothing and you feel like, yep, I finally got figured out. I'm an imp oster. Have you ever had, has there been a musician in your life that really pushed you to become even better and how so? Well, I'll put that in two categories. I mean, I would say practically speaking to musicians that have pushed me the most are my band. They're both, especially Nathan, my guitar player and Rich, my bass player, they've been with me a long time. They really pushed me to write songs outside of my own sort of historical lanes. And then you, Drew, you should try to write a soul song, Drew, you should try to write a song that's in, you know, in B flat, because you've never done that and maybe that would be a stretch for your voice to get up there and sing. And really, like my, my Mount Rushmore is sort of a bit of a sort of standard, the best of the best songwriters. It's, you know, it's Dylan Springsteen, Petty , John Prine. And I think John Prine, more than anybody, when you ask the question about the lyrics. I mean, he has a song, he has a line in a song that called "Life is a Blessing, It's a Delicatessen." So when you hear me, you know, when you hear me try to, you know, rhyme, shell Silverstein in a song, that's me trying to put on my John Prine hat to a degree . But then Tom Petty does a great job. One of my favorite things about his writing is that if you take a Tom Petty song and you print it out, pretty much every single line or stands up on its own as an interesting sort of piece of prose. Right. And so there's an editing, you're always learning from the best at how to edit and how to keep things sort of simple and. And there's so many of my peers as well that I respect. I just went and saw this guy play last night named Stephen Wilson Jr. who's written more than the most sort of beautiful records I've heard in a long time called "Son of Dad." It's an album about his dad passing away young. So I'm still really inspired and energized by the work. I really enjoy all three parts of that music making that I talked about earlier . And so I really love it. I mean, I just love what I do. That's awesome. Your wife Ellie is also a musician and you two singing "The Wine We Drink." It's one of my favorite songs. I mean, I love it. It's incredible. [BLANK_AUDIO] [BLANK_AUDIO] [BLANK_AUDIO] What's the story behind that song? Yeah, we were, we had been married just a couple of years and since an older song for us and I was, I was, I was really blown away by how different marriage was and what everybody told me it was going to be like. What I found was that the, some of the most mundane moments where I felt the most known and connected, right? And I think that's essentially what the, that 's the possibility that marriage offers is to be known and to have someone to know someone, you know, and so I was thinking about the dirty dishes in the kitchen sink. And there's again, another one of those word exercises "The Wine We Drink" dirty dishes in the kitchen sink. And my favorite line in the song is I'm not a sunsetter, Hurricane or Vince Adv ango. This idea that it wasn't all exactly picture perfect that I imagined it would be. But at the end of the day, I'm so confident in that connection and the possibility of that connection that that's where I'm sort of hanging my, hanging my hook, you know, is on, is on that. And so, my, one of my favorite moments about this song is I played it for another songwriter. This will give you like a little insight into my personality. I played it for this friend of mine who's a songwriter. And he heard it and he goes, "Man, I really, I really like that song." He's like, "What if you change this and what if instead of the made the chorus?" And he started like kind of giving me some, and I said, "Oh, his name has been. I said, Ben, I was just playing the song for you because I, because like I want you to hear it. I'm not asking for your input." So the song is finished and I love it as it is. And I'm glad I did that because it's become one of our most sort of popular songs over the long run. I've had to, that's like an, sort of an instinct, you know, person. Is a leader you got, and creative person, you got to have that conviction, right? Absolutely. Yeah. How do you get rid of the too many cooks in the kitchen? I can easily see that happening. Yeah. Yeah. I mean, there's a big, I think there's a big learning curve in our world where everybody's really nervous to prove themselves as a songwriter, as in the studio and then on stage as well. And it's, it's, it's very easy to let a lot of voices in. And there's a fine line between the wisdom of learning from people who are better than certain things than you. But then also the other side of the coin is people can push you off your path. And I think that's a really dangerous thing for creatives, especially because you can chase success. I'll give you a great example for me. When I was young, my first record, I've had a lot of success on TV and film. We 've had about 150 different TV shows use our music in the, in their background, you know, anything from house to parenthood to. I mean, just all these different songs, you know, shows of use our music. And my very first TV sync I got, we were broke and I got this show on, on, on, I don't remember what channel was on Lifetime, used the song of mine and they paid us like $3,000, which at the time I was like, Oh my gosh, this is a made this is incredible, you know, 24 years old got a $3,000 check. I was chasing songs for TV and film and trying to write song I'd listen to a song on TV. And then I tried to copy it kind of right, right, something that sounded similar. And that whole thing dried up. And then one night I'm sitting at home and my sister had called me that day. At the time I heard three kids were very little and they were sort of our, our biggest cheerleaders in the world. And then my sister's career was in the tank. This is, this is when nobody was coming to see us play 10 to 15 people a night. No, it was not going well. And I got really sad that night because my sister told me that they were leaving Nashville and moving to Panama to my, my, my, to go do sort of a mission, mission work down there for three to four years, ended up being longer but I was sad about my nieces and nephews leaving and they were little and I sat down and just for three chords. Wrote this song called lift forever and I wrote the song straight from the heart. It was not for TV wasn't for radio wasn't for success. I wrote this song as a gift as a to my nieces and nephews. And that song gave us a career. And it, it was, it was incredible. It did all this work for us that all of my striving and trying to be commercially viable. When you, what I found and what I sort of taught myself in that moment is that if you're, if you, if you sort of work from the heart and you do something because you love it. That's the only way it can really work in a way that's meaningful, you know, to the world and to yourself. [BLANK_AUDIO] [BLANK_AUDIO] [BLANK_AUDIO] [BLANK_AUDIO] A funny story about that. There's a line in the song that says, "Some people say faith is a childish game. Play on children like it's Christmas Day." So after I wrote the song, I played it for Ellie and she loved it. But her one criticism was she goes, "I don't really love that line about Christmas Day." Well, a little background on her, she grew up in the music business. Her dad is a very successful music producer. He found Amy Grant and has done a bunch of great things in his career. And she sort of, he's the gold standard in sort of production criticism. So I said, "Oh, okay, I really like that line. So why don't we just play it for your dad and see what he thinks?" You know, I was willing to sort of, willing to put myself on the line there. I said, "And if he doesn't like that line, I'll change it. But if he does, I'm leaving it in." So he comes over a couple days later and I said, "I got a new song I want to play for you. I play it for him. He's closing his eyes and he's listening to it and shaking his head." At the end of the song, he goes, "Wow, I love that song." He goes, "You know what I really love? I love that line about Christmas Day." Victory! That's great. You're not only an incredible artist. You really have branched out and done well in business. Tell us, we already talked about the Moon River Festival, which you created and got outside of your comfort zone and pulled it off. Tell us about the Magnolia Record Club and the biggest lesson you learned from that experience. Yeah, yeah. I started a subscription record club business. It was basically the idea was, I would pick a record every month that I liked. It was a new release and get some sort of unique pressing, whether it was a colored vinyl or get it signed by the artist, hand numbered and stuff like that . It was a subscription model. We originally thought we'd get 30, 40, 50 people to do this every month and then we'd make a little spread on the retail piece, retail side of it. In 18 months, we ended up where we got to 2,000 subscribers. I learned some hard lessons on that too. I realized we got to have 2,000 square feet of air conditioned, pallet access space to pull these records. We need 3 employees and we got to have new new ones. No one tells musicians, David, that they're starting a business. We're just a bunch of dreamers and all of a sudden we learned all these really tough lessons the hard way. But it was really successful. We ended up selling it to dual tone records. That was my first experience and starting a new business and selling it and getting a little bit of money and going, "Oh, this is kind of fun." My business school has been 20 years of starting all these random LLCs and learning the business. It's been really fun. I think the other sort of the best thing I've done as a business person who's a musician is not signing a record deal. I own all my own recordings and masterwrights. We've all, I don't know if many of your listeners know this, but the music business basically flips every 10 to 15 years. It was records, well it was singles, then it was full length records, then it was A-tracks, then it was tapes, then it was CDs, then it was downloads, and now it's streaming. And every 15 years, these, whatever happens, it just flips the whole thing into a disarray. And I've lived through two of them as a professional. And the most interesting thing is when streaming started, most of us, I started in the CD era and we were all really hesitant about iTunes because we thought it was going to ruin our business. Because people were paying $15 for an album. Now they can pay $1 for the one song that they like. It was pretty problematic. But then we also realized we didn't have to pay, we didn't have to distribute physical product to 50 states and 500 stores and hopefully if they didn't sell, then they send them back to you and you got to pay them to send it back to you. So the download era sort of put a band-aid on the whole thing, but then streaming, everybody was afraid that it was going to tank the whole thing. Because now not only are they not going to pay a dollar, they're just going to pay $5 to listen to whatever they want all the time. But for those of us who own their own music, it's been really interesting to see. It's actually added a lot of really great long-term value to the place now where you have these huge money firms like BlackRock that have funds really go out and buy rights. And it's been fun because it's given us a lot of stability financially to do what we do because the back catalog has all this sort of permanent value. And there was an accidental great decision that was caused by nobody wanting to sign me when I was 25 years old. And you've learned how to start up all these companies. You said your business is just sort of business school of hard knocks. And what do you think has been, if you had to pick one thing, what do you think has really been the key to you being able to figure it out? Because you've done well. Yeah, yeah, that's a great question. I think curiosity for me has been my best weapon and then good partnerships. I've been really fortunate to have good partnerships. My manager and his wife, they're both managing Paul and Samantha Steele. And we're attached to the hip on a lot of different things. And then, you know, I've been really lucky with, honestly, David, from the time I was 10 years old, until now, I've been the luckiest guy in the world with older, thoughtful people who have been willing to walk out my questions with me. That started with, in scouts, my scout master was really thoughtful. His name was Michael Kearns. And he was willing to meet with me to talk about, you know, school and where I want to go to college and this and that and then fast forward to college. I've got those kind of mentor figures. And I've got that now in my life through people that I've met through golf who were in business that I can call and say, Hey, I've got this idea. What do you think about it? Am I stupid? Am I great? And they can tell me that 's a great idea. But have you thought about it like this? And so that curiosity that I've had, I think I'm good at asking questions. I like people. I like learning from other people. I just have sort of an insatiable appetite for learning new things and being around interesting people. And it's put me in some really fun rooms and it's given me a great palette to paint on as a creator as well as a songwriter, especially. And then I'm also willing to learn, you know, when I told my dad I was a history major, which, you know, a lot of people say, well, what are you studying history for? You can't do anything with that. And I told my dad, so I think I want to be history major. He goes, that's great. If you learn how to learn, you can do anything you want with your life. You have a great father. You know, you're blessed. You know, that's got, he's given you so much good advice. You're also a co-owner of Sweet and Scove Golf Course and Bourbon alongside with Peyton Manning and a few other friends. What's something that you've learned as a musician that you carried over to try and grow that brand? So owning a golf course is tricky, right? Because it's high cost, you know, the weather can change your cash flow. We're a public course, but we sell these day passes and we've got great. We've got a great niche market. One of the things that somebody told me when I was a young artist was don't chase everybody as your audience. You only want your fans. You don't want everybody else's fans. There's a lot of ears in the world. You got to go find your ears as a musician. And I think that's definitely translated to Sweet and Scove. Like, we're not for everybody. We are, we have a niche that is really unique. It's really special. And so it's like to super serve those fans. The most important thing I can do as a business person, as a musician, is to super serve my core fan base. So to deliver great VIP options to communicate clearly when there's tours to give them early access to tickets. And to make sure that they know about things before the general population does to tease songs to them to sort of over deliver what they love about what we do from a touring and from a recording perspective. If we can super serve that core fan base, they stay with us forever. So the experience what that means experientially is that I love it when I see somebody bring their kid to my show. Kids always remember their first shows. And what's interesting about this is most of my favorite artists were making music before I was born. Like I said earlier Dylan, Springsteen, Tom Petty, John Prine. But those guys were at the peak of their careers in the 70s. I was born in 1982 . So when I right now, which I feel like maybe I'm at the peak of my career as a 42 year old. When I look in C7 8 9 10 year olds, I plan on doing this till I'm 75 80 years old on stage I saw Chris Kristofferson at the Ryman as a 75 year old before he got sick. And I thought to myself this is my true north, I want to be on stage still playing my songs 75. And so that translates to super serving like the golf community super serving the bourbon community that is our community. And not trying to be all things to all people. But to really serve the people who are already bought in and then they will continue to grab and loop other people in with them. And that's what we've seen with our with our with our career. I'm really proud of that. I feel like our fan base is not just. They're not casual drill over the neighbors listeners their fans their music is a part of their life. That's such a great insight and you know it's a key to any successful business but not many people get it. We'll be back with the rest of my conversation with Drew Holcomb in just a moment. As you've heard us talk about Drew is both friends and business partners with fellow UT alum Peyton Manning. And in this episode of How Leaders Lead, Peyton talks about the importance of being curious and asking questions. Most of the coaches that coach me would tell you that I asked a lot of questions and to me I was the first to admit if I don't know something tell me what's happening here. I'm not sure what this defense is. If a quarterback doesn't ask questions. I think he's going to be in trouble and I've asked more questions in the second chapter about all these different ventures because I'm not an expert. I don't know the answers. Let me be around somebody that knows more than me and pick their brain and try to get smarter in these ventures. Go back and listen to my entire conversation with Peyton. Episode 104 here on How Leaders Lead. You know I also read Drew that recently you said you're moving and I quote out of the left lane going 90 miles per hour. Okay, just something a bit different for you and your band. You know where are you headed and what was it that really drove that changing course. Yeah, yeah. Just to sort of get into the nuts and bolts of it. There's with touring you know for us people might come see us play and they may come see us play you know at a big theater and we sell out a nice big theater and have a good show in one town. Let's say you know we're in Dallas and we play this big venue and have a nice night and everybody feels great about it. But then two nights later we're in a let's say like an Oklahoma City and we're on there on a Tuesday and it's you know the crowd's 50% sold and you know it's just a it's not very even because we didn't make it on radio. We made it through this sort of through TV and film through opening for other bands through people's play listing through family and friends sharing music. Where we have bigger fan bases is often very organic so we could be in Seattle and sell 2000 tickets and then maybe we go over Spokane and we only sell 500 tickets. And so it's does nothing doesn't really make that much sense and so for a lot of years I've chased. I've been chasing evening that out trying to bring everything up to that. And what I've learned is and you know all due respect to the people of let's say Des Moines Iowa. If I'm playing Des Moines Iowa on a Tuesday night and I'm probably losing money . I've been doing that kind of trying to build like intentionally build build build for a lot of years and I've probably reached a place where I need to not do that as much I need to be home with my family and be writing music recording music. What I basically figured out is I was averaging 80 90 shows a year. And if I cut the bottom 20 30 shows a year I'm actually going to make more money and I'm going to be home more. And at this point in my life that's a high value to me. And so sort of just taking a little bit more of a laser microscopic approach to the to the sort of nuts and bolts of the business. I know that I have more time to be a neighbor, a friend, husband, a wife, but also to be a better have more time for songwriting and recording. And so it's just a matter of slowing down my travel. I said, you know, I'm still going to be going 74 on the right lane. Like I'm still going after it. But the 90 miles an hour, you know, breakneck speed all the time. Go, go, go, build, build, build, tour, tour. I just don't need to do that anymore. And there's also really figuring out the cost on the other side, both practically like I was saying financially, but also the cost to my body and to my family. It just it was time to make a to make a shift and a turn. And I'm really enjoying trying to do that. I'm not necessarily succeeding, but I'm trying. You know, that's so interesting though, Drew, because in every business, the heavy users key, you've got 20% of your business that makes that makes 80% of your money. You know, and you know, you intuitively, that's really what you're doing. You've really figured out, you know, how you can maximize your time and your profitability by being so being more focused, you know, which makes a hell of a lot of sense. We came up with this thing this last year that was really, really was really fun. So again, because I'm known for being a bourbon enthusiast, you know, just like everybody in a lot of businesses, the costs over the last four years have gotten pretty, you know, gotten, gotten up a bit. So let's say, for instance, tour bus costs have really gone up. What I've also found because I've super served my fans for a long time is that they, a lot of them really kind of know me know my story. And so we added this sort of hyper VIP piece to our touring called bourbon on the bus, where we sell 10 very high dollar tickets to people that can come. They want to see the curious about what a bus is like. They come sell the bus for 20, 25 minutes, and they do a Q and A with me and we have a bourbon. And I was really nervous about this because that's a pretty long period of dedicated time to potentially have some awkward experiences with people you don 't know. David, it was so much fun. My fans are just very interesting people. They brought great questions. They had great stories and I would start it off and say, all right, I'm going to start off. I'd love to know how everybody heard my music in the first place. You know, and somebody would say, oh, my cousin played it for me at Thanksgiving or I heard you on the, I heard your song was the March Madness theme song last year and I shazammed it. And somebody said, Oh, I heard it at a wedding. My niece got married and you all were the first dance. And so it starts this storytelling thing and we had this great experience. Again, we super serve these people. They had a really a great story to tell on a photo to take home about the time they got to hang on a bus and one of their favorite musicians. And we got to pay for our tour bus. You know, it was just like, it was a great, it's a great trade off. And it was just a very practical, thoughtful sort of way to go. How can we take some of the things that we know. I love that I'm known for that our fans know that and meld them together to help solve a practical problem that we're having with rising costs. And it was a, it was very successful. We're going to do it again for the next tour. Great, great story. You know, this has been so much fun, Drew. And I want to have some more with you with my lightning round of questions. So you ready for this? I'm ready. All right. What three words best describe you? Grateful, relentless and energetic. If you could be one person for a day beside yourself, who would it be? Can I pick a time as well? Can it be like Tucker Woods, 1999? You can pick it all. Okay. There you go. What's your biggest pet peeve? Oh, bad travel etiquette. I just can't, I can't abide bad travel etiquette in the airport. I, I, all the people could hear the thoughts in my head in an airport. Nobody would like me anymore. Who would play you in a movie? Well, I'd like to think it would be somebody, you know, like a, like a Brad Pitt, but that's not, that's probably not going to happen. What's the guy, just now that I'm going bald, I'll go with Jason Statham. Okay. What's something only a Tennessee ball would appreciate? Well, you can't see it right now, but I'm holding up the, the checkerboard, Tennessee orange wallet that I carry in my pocket that reminds me all the time of where I come from. What's your favorite venue to perform in the United States? Without any hesitation, it's the Ramen Auditorium in Nashville. Now you and Ellie do kitchen covers series on Instagram. What's a song you've got in mind to perform next? I'll be honest, Dave, the song I want to perform next is always the song that I 've written the most recently, which is a new song. It's not really a cover, but it's, but I want to play it for everybody. It's called, anyone could have been anybody. I like that. What's your most prized possession from one of the many things you collect? Oh, man, my guitars, my guitars are my babies. They all, they all have stories. They have songs. If there's a fire, I am running to this room and open the window and hoping somebody's down below to catch them all. Speaking of collections, you, I understand you have over 400 bottles of bourbon in your home collection. What are your top three Berbins? Well, I've got a bottle of Weller 107 from 1963, which is when the original P appy Van Winkle was still making it that I've never opened. That's one that was given to me. That's my top one. And then, of course, Sweetin's Cove, because it's our bourbon, which I love a lot. And then there's a bottle called Jefferson's 16, which is the one that started my collecting and started this expensive hobby. So that one will be the, would be number three. I'm going to send you a bottle of our Valhalla bourbon so you can give that a shot, you know, see if you like. Oh, I would love to. Yeah. What's the biggest lesson you've learned from being a pilot? You don't have to be anywhere, meaning, you know, as a safety thing, it reminds you that you don't have to be anywhere if it means risk in your life, you know. So it's a, it's a good thing to remind yourself that anything can be missed. If it means, you know, protecting yourself to live another day. What's the one thing you do just for you? I mean, it's probably, it's probably golf. It's pretty much just a completely selfish endeavor. [laughter] What's something about you that few people would know? I almost died in 2016 from meningitis. And while it was publicized that I was sick and in the hospital, what I experienced and the perspective I gained and how close I actually was to not making it through, I think is pretty, is something most people don't know about me. Can I ask what that perspective was if you could boil it down? Yeah, I think that's where the gratitude started and sort of the ambition got a nice sort of pad around it. I went from just hard charging all the time to really learning to stop and take inventory daily of what's good and what's right and how lucky I am. Alright Drew, that's the end of the lightning round and thank you very much for sharing that and just a few more questions and I'm going to let you go. Tell me about your annual State of the Union trip. Yeah, that's just one of my favorite things that my wife and I do. You know, we live very busy, logistically challenging lives like most people do , especially people who are in leadership who are probably listening to this. And what we found was that taking an annual trip for three days to do sort of a reset has been an absolute must for us. And so we typically do it in January. We go somewhere warm and we have big conversations and so the conversations are kind of following our three categories. One is a look back. So we look back at last year, we talk about the challenges of last year, what was great about last year, what was difficult about last year. Both professionally, personally as parents. And then the next one was we look forward and talk about what we're excited about about the next year, what we're afraid of for the next year. And then we do a practical third conversation where we talk about, you know, basically finances and state of our of our of our life, practically speaking and all the details with that. And then the fourth thing we do is that meals, we ask each other questions and the only rule is every you rotate who ask a question. And you both have to answer it so you have to answer your own questions as well . And it's been a it's been we've been doing it now for about 18 years we've been married almost 17 years we've been married 19 years so. It's been a really important piece of the pie and I think for me I would say that that. You know, having Ellie and keeping that relationship sort of healthy is the most important indicator of how well I'm doing. I'm a better songwriter we're doing well I'm a better band leader when we're doing well I'm a better businessman when we're doing well, a better dad when we 're doing well. And that trip has given us a lot of fuel and a lot of sort of vision for what life could be. I love that I love that. What would be your unfinished business true. I have so many dreams that I've decided to put away because I I'm never done making the record that I that I dreamed I could make. I think there's always even when I finished one and I'm really proud of it. It always it always feels like the work is never done, you know that there's always new stones to unturned new things to say, which songwriting is also a bit so very personal so you're always, you know, you're always growing as a person so you have more to say and more to do and more work to sort of unearth the heavy lifting and. But I always also, you know, there's this there's this writer named and a lot and she says the perfection is the is the is the voice of oppression there's because there's no such thing as perfection. And I would say if I have a superpower it is knowing when something is ready and and putting it out there and letting go of it and and then celebrating the work. And so in a way all all work is a bit unfinished because we're humans and you can't there's no there's no such thing as a job perfectly done. It's a task perfectly, you know, as a yard perfectly maintained or a round perfectly played or a song perfectly written and chasing perfection I think is is is is just a fool's errand and it sure is it sure is enticing you know. Alright last question. What's one piece of advice you'd give to anyone who wants to be a better leader. Learn to listen. I think that if I could go back and look at any of my major crisis moments or moments where I made made major mistakes. Probably someone speaking up that I wasn't listening to, you know, or person I wasn't seeing because I was too busy, you know, sort of in my in my hard charge spirit so but I also think that relates to listening to yourself and sort of knowing your own conviction. I'll tell this one story about a musician it's a quick story. I have coffee a lot with young artists and I wish that he had sort of taken his shot and that's what I mean by that is he said I want to get coffee to talk about music and I said okay great. I got one hour meet me at three o'clock at this coffee shop down the street. And we sit down we talk we're just small talking we're small talking and I admitted decision I was not going to I was not going to start the conversation this is him he asked me for coffee. So with four minutes left in the hour I said, can't remember his name is probably better than I don't remember his name let's say his name is John. John, you have wasted my time. More than that you have wasted your own time. You had an hour with me to ask you anything you wanted about music and you didn 't shoot your shot you just sat here waiting for me to lead the conversation. If you want to talk again call me in one year from today and bring a list of things to talk about. But until then don't reach out to me and ask me any for any advice because you wasted my time. And he didn't shoot a shot, you know, that's a song for you Drew. Shoot your shot. That's a good one. You know, Drew, you know, I love your music and I really feel blessed. I've gotten to know you and you know one of my favorite songs is Fly and that you've written and sang and the other one I love is Gratitude, you know, which is a great great great song. And I bring those up because I think anybody that listens is podcast you'd listen both those songs for sure. But I also bring it up because I'm so grateful for you. You're an incredible person. My life has been enriched because I've gotten to know you. I love how you think. I love how you care about other people and I love how you lead. So thank you very much for being on this show. It is my honor. I feel very strongly in the same direction back at you. Thanks for being my friend and invite me into this beautiful thing you're doing. Make no mistake about it. Drew understands the power of super serving his core customers by giving them more of what they already love. This creates happy lifelong fans who bring their friends along too. In every business you've got to find your heavy user. Look, I know it's natural to go after your barely engaged users and get them to spend a little more. We all want to broaden our reach. But you can waste a lot of time and resources that way. Remember, sometimes it's better to invest more in the people who really value what you offer. Rather than trying to convince the people who don't. Okay, at this point in the show, I usually give you some way you can apply the episode's big idea. And you should absolutely think about how you can super serve your core audience. That's the big idea in this episode. But since it's the beginning of the year, I want to do something a little different. This week, just spend five quiet minutes in your day and play Drew Holcomb's song "Gratitude". Focus on the lyrics. Let them really sink in. Savor them. Really feel what's in that music and the intent behind it. Because when you have that attitude of gratitude as a leader, I'm telling you, almost everything else gets easier. When you get that state of gratitude, you go to work, you go with great anticipation, you go with your mind open to learn, you go with your mind open to hear from other people. And when you get in that state of gratitude, you make your very best decisions. Because believe me, you are moving up that mood elevator to the very top. And when you're moods where it should be, you're the best place that you can be . So do you want to know how leaders lead? What we learned today is the great leaders super serve their core audience, their heavy user. Coming up next on How Leaders Lead is Pat Kelsey, head coach of the University of Louisville. And this guy I can tell you is a guy who knows how to begin a turnaround and I predict big things for the University of Louisville basketball team going forward. When you're having a lot of success, sometimes you kind of take your eye off the ball a little bit and you start looking around about like, "Man, is this next opportunity going to come?" And sometimes when you do that, you're less effective in the position that you're in. So be sure to come back again next week to hear our entire conversation. Thanks again for tuning in to another episode of How Leaders Lead, where every Thursday you get to listen in. Well, I interview some of the very best leaders in the world. I make it a point to give you something simple in each and every episode that you can apply to your business so that you will become the best leader in the world. And one more thing everybody, happy new year. Let's make 2025 the year of leadership, the year we all get better and better at what we do. We all get better and better at what we do. [BLANK_AUDIO]