EntreLeadership - #376: Keeping Your Dream Alive with Drew Holcomb

Episode Date: May 25, 2020

As many an entrepreneur will tell you, what originally starts as a dream opportunity can all too often turn into a never-ending nightmare. But Drew Holcomb refused to let his story play out that way. Rather than simply focusing on the creative side of his career over the past 15 years, the singer/songwriter doubled down on infrastructure to build a thriving business (in an extremely competitive industry, no less). Tune in as Drew shares how he balances priorities and navigates change, and what he loves most about his job.   entreleadership.com/podcast Drew Holcomb's website #372: Going All Out in Your Business with Paul Steele   Songs mentioned: Live Forever Fire And Dynamite See the World Family Maybe You Never Leave My Heart Dragons   Moon River Music Festival Magnolia Record Club Amelia's Flowers Watch the Kitchen Covers Buy the Kitchen Covers on Vinyl Drew Holcomb on Instagram Ben Rector's website The Ideal Team Player by Patrick Lencioni Rocket Fuel by Gino Wickman and Mark C. Winters Drew and Ellie Holcomb's A Neighborly Christmas concert Kitchen Covers - Learn to Fly Family music video   Difficult Conversations Checklist Review this episode for a chance to win a $25 Amazon gift card   As an Amazon Associate EntreLeadership earns from qualifying purchases.   Want expert help with your business question? Call 844-944-1070 and leave a message or send an email to [e-mail]. You could be featured on a future podcast episode! Learn more about your ad choices. Visit megaphone.fm/adchoices

Have you noticed that we live in a world today that is absolutely obsessed with labels? Type A, logical, creative, your enneagram number, your Myers-Briggs. But what's so sad is that all too often, leaders hamstring the growth of their business because they allow those exact labels to become limits. From the Ramsey Network, this is the Entree Leadership podcast, where we help business leaders grow themselves, their teams, and their profits. I'm your host, Alex Judd, and today our conversation is with Music City icon, Drew. Holcomb. And you may remember that we talked to Drew's manager Paul Steele a few weeks ago,

but here's the thing you need to know about Drew. He absolutely refuses to be limited by other people's labels. Yes, he's a killer singer and songwriter. And believe me, you're going to want to listen to the end of this episode. But he's used that foundation of singing and songwriting to lay a platform for becoming an entrepreneur, an investor, a business owner, the guy's creative, he's discipline. He's an absolute anomaly. But all of these different roles and qualities, they've come together to make for a pretty remarkable and outrageous life. But as you will hear, his path toward becoming one of Americana music's most beloved and authentic figures, it was one that actually started over 20 years ago. And it was birthed out of a tragedy.

I played music all throughout high school. I was your classic, like, guy with the guitar playing a young life and, you know, learning songs and having fun just with friends. I didn't write a song until I was a junior in college. I went through a personal tragedy the summer after my junior of high school. I had a younger brother with special needs who passed away very unexpectedly. I was actually out of the country. And music was sort of the thing that kind of got me through it. So really, for me, music was this personal sort of healing. Like an anchor? Yeah, anchor. Yeah, exactly. I had no thoughts of doing it professionally. Were you especially talented at that time?

I don't think so. No. No, not really. I mean, I was fine. You know, I always had like a very sort of earnest, hardworking, like, plow through it sort of ethic. You know, I was, like, involved in scouts and was in the student body organization and all the things. You know, in school, I loved school. I was always a good student.

So I went to school to college with the intent of going to graduate school to study history. And my goal was to write books and be a history professor. So that was the dream. Hmm. Now, somewhere along the way, my junior year, I decided to go study abroad, and I studied in Edinburgh, Scotland, and I didn't really know anybody. So, obviously took my guitar with me because, you know, that was like my main hobby was playing guitar. And I just started writing songs. Like, at night, I'd finish my work or whatever.

I had three roommates of Frenchmen, Frank, Thomas, the German, Dave, the Canadian, and me, drew the American. That sounds like the makings of a killer band. Yeah, that's right. That's right. Ken Cades Court. What were you studying in Scotland? I was studying church history. So studying sort of like a variety of classes, but I was studying sort of 15th, 16th century

Scotland. I was studying the early sort of the early Roman church. So sort of Constantine through, you know, the breakup of the Roman Empire. So just like nerdy stuff. And just had your guitar with you the whole time. Yeah, totally. I wasn't writing songs about any of that stuff. I mean, it was informing, you know, in a way.

But I just started writing songs and really sort of was diving into that pain because what I knew I was going to do was I started writing songs because my senior project at UT was an oral history about my brother. So I was interviewing 50 to 80 people, nurses, doctors, friends, teachers, cousins who grew up around him and knew his life. And I was trying to figure out why this kid with Spina Biffin had made such an impact. When his funeral was like 2,500 people. Oh my word. So I was just personally curious and also just thought it was a great way to sort of put this history stuff to work to do this oral history. And so part of that was I started writing songs about that sort of as a sideline. The next thing, you know, I come home from Scotland and I started my senior year.

My friends, I started playing some songs for my friends. They're like, hey, man, these are pretty good. You should maybe give this a go. And so I started booking some gigs in Knoxville, like at bars. And I'd play covers and some of my originals and invite my friends out. And this mentor of mine basically told me, said, hey, man, graduate school can wait a year or two. Like, it's not going anywhere. Why don't you take a break?

Do this music thing. Get a job. See what happens. And that was in the fall of 2003. And here we are in 2020. Golly. That's crazy. So when you started doing it and you were playing in those bars, you couldn't have been making much playing in those bars and stuff like that.

And it was probably pretty scrappy beginnings for a while, I would assume. Oh, yeah. I mean, really four or five years of absolute scrap. Absolute scrap. Was that whole time were you thinking yourself, this is what I want to do with the rest of my life, or were you just filling time during that season? I was enjoying sort of the process of seeing the country

of convincing my then friend, Ellie, to date me and marry me. I was enjoying the freedom. I really found a lot of freedom in being my own boss. That was like all of a sudden, I was like, well, that's pretty cool. And then also at the same time, I was sort of looking at the writing on the wall of the other dream and going, man, it's like really hard to get a real decent job at a university, especially as sort of, you know, another southern white male. It's just like there's a lot of those with PhDs in history. You know, pretty saturated.

Yeah, it's a saturated market. And so I just, honestly, the part of it, I was really loving the business. And I was finding satisfaction in putting together the band and the recording process and learning. I was growing. I felt like, you know, all these things I didn't understand about music. I mean, as a kid, you get a record and you think, oh, these people just got in a room. They set up some microphones, push record, and that's what you hear. And then you realize that, oh, it's actually this incredibly long and arduous process, but a very satisfying process.

And so I just found myself enjoying it and just kept going. And I basically told my dad, you know, I'm just going to keep doing this until it stops growing. Hmm. And it didn't. And you're still here. You're still doing it. Yeah. It's still growing.

Was your dad. supportive or your parents supportive as you were kind of pursuing this dream very supportive you know my dad always jokes he says he has all these friends that tell him like why did you let drew do this and he's like i didn't let drew do anything you know he's 21 years old graduated from college i didn't have any debt which was nice i was on scholarship it makes a big difference when you're 22 years old about can you pursue this dream well i have all this debt and i got to get a certain amount of money job or can i like go try to do something independently well it sort of hamstrings you so i didn't have any debt So my dad basically told me like, hey, man, if you're going to work hard at this,

your mom and I are in your corner. Like, let's go for it. And he actually took me to the guitar shop and bought me like the nicest guitar you could afford and said, like, this is our send you on your way thing, you know. Wow. So very supportive. So I've had other, you know, people say like, wow, why did your parents just let you do this crazy thing? I'm like, I didn't let me.

I mean, I was an adult. Yeah. You know, that's right. You don't have to have your parents' permission. But it sure helps psychologically, I think. To have people that believe in you that they're in your corner. Big deal. But also they weren't covering it.

Like, they weren't paying for you to do this. They weren't funding your dream, but they were supporting your dream. Yeah, but that gave me a loan. 10 grand to make my first record, but it was expected to be paid back. And did you pay back? Of course. There you go. I figured you're probably not still on the payment plan for that.

No, no. I read this in, I think it was Rolling Stone that wrote it. It said, while working at a Memphis studio in the early 2000s, Holcomb started playing in small bars on weekends and eventually found themselves zigzagging across the south. in an old Volvo wagon and putting nearly 300,000 miles on the car in five years. First of all, is that true? Very true. Oh, my gosh.

And actually totaled it around 240,000 miles and took his own mechanic, and he made it driveable, and then I put another 90,000 miles on it. That's insane. You were going all over. And then it says, initially, he says he was barely making ends meet, playing at the most random coffee houses and community college lunch hours, anywhere that would give me a little scratch to play my songs. So that's a pretty accurate representation of those first few years.

Yeah, yeah, definitely. And, you know, some of those college gigs were literally community colleges at noon, and they had these entertainment budgets that they had to spend. So they'd bring you in. I had to bring my own PA in. So I'd be over there. I'd set it up in the corner and start playing. And literally a third of the room when they realized that somebody was sort of interrupting their lunch,

would put their headphones on to listen to their music while I'm playing in the corner. So you had to have pretty thick skin. Yeah, no thing. But, you know, their checks cashed. And that's how I was able to afford to keep going. So it was complete survival. Did you have moments where you were just like, what am I doing? At least two or three times an hour when I was playing those shows.

I mean, seriously, though, you know, sometimes about halfway through that period is when I got married. And Ellie was a school teacher. And then after a year of teaching, I convinced her to go on the road with me. And so really my last year of doing a lot of those college shows, she was with me. And that was so much more fun because we were just getting the car and just laugh at how terrible the experience was. You know, but like I said, the gigs paid. And that was right around the time we started having some success with songs on TV and film. This song called Live Forever came out, which did really well on TV.

The show, Parenthood, was a season finale, sort of montage moment. And we got paid enough to get a van. And we started getting asked to go on tour with, you know, other singer-songwriters like Dave Barnes and Mark Rassar, these sort of smaller, you know, club things where all of a sudden we're starting to really make real fans. And then it became, maybe I want to do this for the rest of my life. But up until that point, it was like, this is a big maybe. You know? Like there was this possibility that there could be a brighter future, but there's also a possibility that's like we could be a community colleges for a long time.

Yeah. And at some point, yeah, at some point, you know, you have to sort of make decisions about what you want your life to look like. And actually, my dream in high school was to have a lot of military and my family go to the Naval Academy. And I had that opportunity, didn't go. Which that's pretty remarkable. Like to get into the Naval Academy is a pretty big deal. Yeah, it was an incredible deal. I have a lot of, again, a lot of family from the Navy,

and so they sort of helped me through that process. But then all of a sudden, I had to just gut check about it. So fast forward to sort of the middle of this really intense four years of doing this, and it wasn't going very well. And I had started the process of trying to think about joining the Marine Corps so I could go to JAG and get, like, graduate school paid for. And if that happened. is music kind of like, okay, that's just not going to be what I pursue?

Well, that was basically what Ellie and I reached a point where we were like, it's not going very well. We're having a hard time paying our bills. We need to fulfill the rest of this year's obligations and release the songs that we have and let the chips fall. And if something crazy happens in that time that says keep going, we'll listen to that. But if not, this is the new plan. Okay, so I want to park right there for a second because, you know, we exist for the small

business owners, right? So two to 200 team members. And we talk about the different stages of business. And that first stage of business that we find so many small business owners in is what we call the treadmill. Yeah. And I like to call it the dreadmill, right? And it's just like we're always doing what we've always done. And it just feels like it's just moving faster, but it feels like we're trapped by the thing that we're created.

And like we're not having a ton of fun. We got into this thing for freedom and this doesn't feel like freedom. Honestly, there's a lot of parallels to what you're talking about of like, I'm playing at these random community colleges. Yes, I'm making money, but this wasn't the life that I necessarily envisioned. and stuff like that. What is the narrative you have to tell yourself in your head when you're in the center of that to just say, okay, it's the right decision to keep moving forward? Yeah, I mean, we basically started creating some benchmarks, and that was one of them,

was that moment I just described, which was we feel like we're on this treadmill. We're not getting off the treadmill. We're making a living, but it's the living that we're making is not worth the headache that we're experiencing getting there. Yeah. If that doesn't change by X point, which for us was that was around these conversations were happening in April or May, our decision was we're going to finish out the calendar year.

And if we still feel this way at the end of this calendar year, we're going to hang it up and pivot to something else. Because we had other dreams. We had dreams of starting a family, you know. Yeah. We had dreams of being a part of a community and not being gone 220 days a year. Yeah. And of Volvo.

Yeah, and of all though. So, and we had dreams of not. basically like having to sort of rely so heavily upon our network of people that we knew personally to drive our business, meaning like, oh, man, we're playing a tree for it. How do we get people to come and tree for it? Oh, we got to call these six people and please can you tell everybody to come? You know, at some point, as a musician, you have to, like the product, the music, if you will, has to do the work itself. Like, people have to want to come hear the music. Otherwise, it's just like emergency every time you have a show just to get people back. And that's not a

sustainable model. So we basically created this time. frame where it's like if we still feel this way at the end of this year then we're going to make a change and then that fall we noticed a particularly like pivotal moment we released the song Live Forever and for the first time in our career we were looking out we were playing cities where we used to sell 70 to 80 tickets and now we were selling 150 to 200 tickets and people knew the words to the song and it was like okay we don't recognize anyone in the room that's a big deal this is a big moment and so I think that's an interesting interesting thing. We started these other endeavors over the years. I always make this joke with

Paul that like you had these dreams, right? And then building the dream can sometimes turn into a nightmare. And then you have to figure out how to like managing a dream sometimes as a nightmare. And so then you have to figure out how to build the right infrastructure and team so that the dream doesn't become a nightmare or doesn't remain a nightmare. That's right. And that's structure and process and people and all of that. Yeah. And money and all this. There's all these little, things about that. So one thing that made that great for me is I was having in those years whenever I'd have a band show.

So we'd have like, Ellie and I would play mostly solo or duo when we'd play in Nashville, Knoxville, Memphis, Birmingham, Atlanta. We'd play with the band. And I was putting together sort of like a different band every time. And so the quality control was like all over the map because it was different players, how hard did they work to learn the music? And I realized that like, oh, you really have to, in order to keep the right guys playing, you got to pay them well.

And so for those band shows, maybe I don't make any money, but I want to create a certain standard. And then what I notice is you create that standard. And then your audience grows because people love going to a show that's good. Imagine that. The quality of the product makes a difference. You know, yeah. And the other players were good players. We just didn't work very hard to create.

You have to spend time with your band to have a cohesive sort of reality on stage. If you don't work at that, then you don't have it. And people in the audience know that. Yeah. We see that so many business owners can take the strategy of, I'm on this treadmill, and they get this story in their head that the way to get off the treadmill is just to turn the speed up and turn the incline up, right? And that's like, that's like you saying, like, we're just going to do 10 times more community colleges and we're just going to do them better. And we're going to hope that 25% less people put their headphones in, right?

I assume that wasn't what got you on parenthood. So what were the deposits you and Ellie were making? in those treadmill seasons that enabled the future success that you experienced after that and even up to now. Yeah, a lot of it was on the creative side was writing more songs and trying to write better songs and taking advice from, before this period, I sort of had a very sort of youthful arrogance of like, I know the way. I don't need to be shown the way.

And so I started taking advice from other artists and other producers and letting other people sort of help me shape my creative vision, help me shape the songs, help me shape the sound of the songs. We got for that song, we started talking to a record label, it's called Dual T-tone, about sort of helping, taking some of the ownership away, but then making the team bigger, you know, and that was a, that was a big help. Yeah. To have a professional graphic designer making your artwork for your T-shirts and you're... As opposed to you?

As opposed to us or just, like, sort of fly by, you know, some weekend or... Makes a difference, huh? It does make a difference, yeah. And so, but it costs money. Yeah. You know, like doing things right costs money. And so we had to sort of get better budgeting and putting money aside. I actually put together a business plan and took on investors for a season.

And I had the rights to buy them out. But basically, I put everything that I did publishing, merchandise, touring, and masters, all in one sort of LLC. You know, and they bought shares of that. And I paid out a preferred rate of return. And then they got a dividend. in and then I also was able to, over time, buy them out completely. And so that gave me some working capital, which I didn't understand. That's the one thing that no one tells you about when you start as a musician.

No one tells you that you're starting a small business. And that's what I was just thinking. And you're just like, oh, like I got to think about accounting. I got to think about payroll. Do you want a 1099 or W2 people? Or is this deductible? Should I? There's just so many decisions to make as a business owner.

And that's, you're not like, oh, man, I want to be in a band so I can run a business. Yeah. But then over time, you realize that that's like a big part of the heart and soul of why bands succeed or fail is how well they set up their businesses and how well they think about those kind of things. I don't know how many people that are listening to this have been to Nashville before, but it's just like, I mean, they always say, how do you find the next hit musician in Nashville? You just say waiter, right? Right, right, right. They'll come bring your check to you. I mean, like everyone in this town is a musician.

Yeah. You go down to Broadway or quite frankly, anywhere to anywhere. And I feel like based on the shows that I've been to, 90% of those people that I've seen aren't thinking about tax deductions and taking outside investors and hiring a graphic designer and what the what the culture their team is going to look like and how they're going to retain team members. Like no one's thinking about that. And I wasn't when I was younger either. Yeah. So how did you develop that acumen? Like you had to learn on the fly as this thing was already in the air how to run a small business because you got into it to play music.

it sounds like that's exactly right i got into play music i got in it to see the world i got it to win the girl too i mean you know honestly that was a part of it you know was that was how ellie and i were connecting was over music i was like gonna make a great movie someday yeah yeah yeah so i had a couple of uh i'd call them mentors business mentors people that have helped me along the way helped me make decisions a guy that was a bass player and memphis a weekend warrior base player He worked for a big accounting firm as a business consultant. And he sort of came to some shows and seen me play. It was like, I think I can help you a little bit.

And so he's still a partner of mine. After all these years, he helped me put together like a business plan and a pitch deck, which I always, these are all new things to me. I didn't know what they helped me set up the LLC and put me in touch with a good accountant. And, you know, just really helped me sort of frame, kind of think of it like a train. Like if you got the songs and the music are the freight. You still got to have, like, the infrastructure of the train itself, the tracks, conductor. Like, you've got to have the infrastructure to get the music and get the creative art.

That's what I think it is. It's art. Yeah. Get art into the sort of market. And that takes, I mean, like, one thing is so interesting to me. I've been making music sort of in three digital eras. Yeah. The first was, I was making my first few records were mainly the primary sales unit was a CD, right?

So, you know, 2003, really, to 2000. And 10, that was the primary, you know, way that I sold music. And I remember when iTunes came out, all of us musicians were like, oh, no, don't do it. You know, it's like, it's only a dollar a song instead of $12 for the whole record. It's like, this is going to kill us. But then we realized that, oh, that cuts our distribution costs. So not the mail CDs stores all over the country. Now anyone even who hears our music in Brazil or whatever can just go and buy it.

And we don't have to send them any physical product. Like there is a great model. So that started around like, I don't know, 2007 and they overlapped for about three or four years. And then 2013 or 14, all of a sudden, the streaming thing came along. And all of us were scared to death of that because it was basically devaluing the market of downloads. And so there were these outside forces on our business that we had no control over. Yeah.

You know, there's these huge corporations of, you know, the DSPs with Comcast and Charter, Spotify, the Amazon, the Googles and Apple's. Like, there's these big companies that are deciding how our distribution model works. And so you kind of have to do the best you can with whatever reality you have. I'm not going to go create, you know, like Garth Brooks has tried to not be on these streaming services and create his own on his website. And I'm like, man, how much market share is he losing by not being on there? That's right. You know, but he's, you know, old school and wants to keep it that way. So we've, I remember when Spotify started, we would hold new records for like four months off the streaming services.

Really? To try to convert as many people to paid customers. You were trying to fight it. Trying to fight it. And it worked at the beginning before they had a ton of market share. Yeah. And then after a while, you're like, this is a bad idea. Like, we were really losing out.

And then over time, all of a sudden, you realize the streaming thing, the cash flow growth over time is really good in that. And all of a sudden, it makes your catalog valuable, which then you got these, you know, there's companies and funds around the country buying master rights. And these are conversations if you told me at my 23-year-old songwriter at a microphone self, I'd be like, what are you talking about? Yeah. I'm going to be a songwriter. Yeah, you're learning how to pivot when the market gets disrupted, and you've now done that. How old are you?

37. Yeah, you've now done that three, like there's been massive market disruptions in the arena that you're in and you had to pivot three times. Jeez. Yeah. You are a business owner and you are operating as a CEO of Drew Holcomb Incorporated, essentially. Drew Holcomb and the neighbors incorporated and just running this thing.

You use the phrase creative vision earlier, and that's one of the things I wanted to talk to you about. I'm just so astounded and impressed by how many things you and Ellie are involved in. Yeah. So, like, what is the vision that y'all are pursuing right now? Well, I just sort of have serial curiosity, you know. And so Ellie has sort of let me loose and said, like, here are our core values as a family. You'll have those?

Well, I mean, yeah, they're not written down, but we sort of know what they are. Yeah, you know what you stand for. Yeah. And you know what you stand against, too. I mean, we had this great, with this great marriage conference, which sort of set one of our standards was, you guy Dan Allender was talking about what, not only need to know what your guesses are, you need to know what your nose are. And so one of Elinai's biggest knows, it's like kind of not on our watch is like human trafficking, right? So we hear about human trafficking, you know, exploitation of children around the world. We are like, we are going to stand in the gap with these people who are fighting this.

So we were like all in on organizations like IJM and the Preemptive Love Coalition. And so we have this thought with our giving that is we want to go deep, not wide. So we give as much as we can to a smaller number of organizations to make a meaningful impact. To make a more meaningful impact and be involved particularly in those particular issues. So that's an example of sort of value. So then we also, you know, time with family, she and I take an annual trip every year called State of the Union away from our kids where we look back at the year behind, look at the moment we're currently in, how we feel about the year behind, and how that affects. how we plan for the year ahead. So we have these sort of things that we know our standards for us personally, regardless

of what our vocation is, you know, and what our musical calling is. That being said, then we also know what gives us life. So, like, for me, I love starting new ventures, you know, and whether that's a new record, which is the main thing for me is I love writing and recording and touring. I love being on stage. I don't like everything else involved with touring. I don't like sleeping in a bunk. I don't like flying in planes all the time.

I don't like having to go to the bathroom, strange bathrooms every day. Not ideal. You know, eating road food. I mean, there's a lot of things about it that I don't like. But once I step on stage, there's two things I love about that. One, I love playing music with my band. I'm surrounded by really talented people who have been around for over, you know, a decade and a half.

So there's this trust thing. It's like, it's funny. I've been watching the last dance, the Michael Jordan thing. Yeah. And we're obviously not the 90s bulls. but I know that feeling when you have the right team in place. Yeah. And the way you know each other and like getting the captain that ship on stage.

And I've got like my Pippin is my guitar player, Nathan Dugger. And so, you know, I know that. So I'm watching. And I'm like, man, this is what it feels like. You know, when you're on stage and you're connecting with your band, absolute magic. And it's probably like, you all, some of you have been together for over a decade now. Oh, 16 years, 14 years. And then the drummer's been newer.

I assume there's an element to that in terms of what y'all are able to produce just because of the chemistry that you have that just wouldn't be possible if you're in year one with someone. Oh, for sure. For two reasons. One, you don't know each other that well. And two, you're a lot better musician at 37 than you are at 22. I mean, by a long shot, you know. But that's your core passion, though, is being on the stage with those guys. And then the second part of that is connecting with the audience.

Like, I love the fact that each room is different. Each city has a different feel, looking people in the eye. I mean, obviously, they're nice when it doesn't go that well. And that challenge, the scare of like, oh, man, this is like, this is happening in real time. We're not pushing play. You know, we actually have to go out there and do this. It's pretty thrilling. Yeah, it's a thrill.

It's totally thrilling. And so I know that I love that. Yeah. That's my main, like, thing that I love is writing music, recording it, and then playing on stage. That being said, after a while, I realized we had this audiences. had these other ideas and thought, well, let's give it a go. The first one was this festival, Moon River Festival. Yeah, and Chattanooga, correct?

Chattanooga. Yeah, we did it for a couple years in Memphis. And Paul and I partnered on that 50-50, and his wife and coworker, Samantha is also a partner on that. And so that one was one of those ones that grew into a nightmare. Really? Yeah, because we were over our skis. You didn't know. Y'all like sold it out the first year, correct?

Sold out the second year. Okay. But either way, it was huge, the first and second year. It went really well the first year. Yeah. Yeah. And so it's a success. and you're like, oh, we did this idea, we did this thing.

But now we've got this, I mean, was it a mess on your hands? It was a total mess. I mean, you know, like, no one tells you when you start a festival that, because all you're thinking, all I'm thinking about is here are the bands I want to play. And here's, you know, what I want it to feel like and like the food. You're thinking about some of the, like, fun parts. But then you're like, so many entrepreneurs thinking about like, we've got to launch this new product right now.

We've got to bring this new service. There's people asking for it. I'm really excited about it. I'm passionate about it. And then three months later, it's like, what are we doing? Why did we tell everyone about this? Totally. What have we done?

Well, yeah, so the day of, we're like, oh, man, we didn't pour a potty. He's been on have enough security. The neighborhood's calling the police because the parking is a disaster. We ran out of ice at 1 p.m. and it's 90 degrees outside. We ran out of ones at 3 p.m. And the only place on a Sunday. And the only place to get ones was the dog track in Arkansas, 45 minutes away. So, I mean, it's like all these just like total.

So by the end of it, we're all like, oh, my gosh, we're going to have PTSD from this festival. So we need a partner. We need to hand this off. So we took on a major partner. Now I just do the creative part. So you legitimately like you are a part owner of the Moon River Music Festival, but you don't run the day to day of making sure all that happens. No, we partner with AC Entertainment, who they do Bonner.

So for that Moon River is like walking the park. So that festival for you is kind of like an asset, correct? Oh, for sure. Yeah. Yeah. How gratifying is that? Yeah. It's like a little annuity.

Man. And you still play at it, right? So you get to show up, do your thing there. I play it. I host it. I do a lot of the PR, like I'm sort of the face of it. Yeah. I show up and do interviews and talk about the festival and stuff like that.

So, yeah, it's been fun. But it's been a long process to figure out how to make this sort of side hustle into something that's fun. That also ties into the main part of my calling, which is like being an artist and being on stage. But my show at Edmund River is so far the last three years has been the highlight of me. show-wise. Really? Every year, because it's just, the payoff is great. Yeah.

Oh, that's too cool. When you have those ideas, because you just seem like a very entrepreneurial mind, I would assume you see opportunities. And because you've got such a brand now, too, you probably have opportunities approach you. Lots of them, yeah. What's the filter that you run those things through to make sure that it's not something that ends up killing the things that you've already built or taking you away from your

passion? Like, what warrants actually pursuing something for you and Ellie? Yeah. I mean, I think a lot of it as a public figure now, which is kind of a crazy sort of way to frame it, but it's true. I sort of have three boxes that one of these has to be checked. One, does it pay well? Two, am I passionate about it? Three, how much time is it going to take?

And so if it's a limited amount of time and it's something I'm really passionate about, then I'll probably say yes to it. if it's a lot of time and the pay is bad, then it's probably like, well, we can't make that work. So it's got to settle somewhere well into those three things. And so there are things we do on the sort of nonprofit side that I don't pay anything, but we're really passionate about them, and we can make them happen with limited amount of time. So, you know, that's how I sort of think through shows that we get pitched,

like, hey, do you want to come play this event? Well, can I, am I going to make money on it? I'm going to lose money on it. Well, you're going to lose money on it. But okay, well, what is it? Oh, man, it's this thing. You've always wanted to go. You know, like if the Pebble Beach Pro Am called me and said, hey, we do a free show, but you get to come play and be a part of the thing, you're like, yeah, I'm in.

Because I'm, but if it's like, you know, I get asked every day through Instagram or through emails of my manager, probably three to five times a day to participate in nonprofit fundraising events for basically no money except for travel. Now, because of my deep, wide philosophy about charitable engagement, I say no to most of those things. But that's pretty huge, though. Before the request came, you had a philosophy. Yeah. And that's what we see. The business owners that spread themselves too thin are the ones that are making those decisions about opportunities one-off as the opportunities come their way. And they don't have a philosophy like you're talking about to turn to you and be like, okay, what do I stand for? What are my three criteria like you said? So I would imagine that gives you a great, deal of structure and focus of like this is who we are. This is what we do.

Yeah. And then there's also like sometimes, you know, I had a brand come to me and they wanted to do a sort of limited edition, Drew Holcomb barrel pick whiskey, you know, which is a cool idea. I love whiskey. Paul, as you know, loves whiskey, my manager. And honestly, they have a great product. But I, you know, I think Paul and I, somewhere down the road because of his sort of work

in the whiskey world being a producer. the documentary and having the speakeasy. And my thing, it's like, is that, because I feel like once you sort of step into that space, that's it. That's your brand association is with that particular thing. That's right. You know, so I just decided, even though it was a fair offer and it was something I was interested in, I didn't need the money to do it.

I wasn't sure that it was the right thing. I'd rather wait and make, if I'm ever going to be involved in that business space, I didn't think it was exactly the right fit. you know so those are decisions you kind of have to make you trying to think long term about your decisions is hard to do yeah are you naturally a strategic thinker or a tactical thinker like are you a doer in the moment and that's where you naturally gravitate towards are you thinking futuristic big picture probably thinking futuristic big picture i'm like you know for instance we're in the studio i'm not the artist that like wants to do a hundred takes really yeah i'm like

i'll do seven or eight takes i'll fix it until i get it right but i don't don't want to just tweak and tinker with it. I changed the oil for the first time ever yesterday. Congrats. That's a big deal. Yeah, it's a big deal. So I'm trying to be a little more tactical. Yeah, yeah.

I feel like especially this current moment, there's more time and space. I'm trying to sort of engage that part of myself. Well, you said you've got, what, six or seven acres that you're mowing? Yeah, yeah. So I got this new zero-turn mower. And I'm like, okay, I learned I changed oil in this thing. And I was like, I'm 37 years old. I've never changed oil.

Like, it's not because I'm some like silver spoon. I'm very impatient. Yeah. So I'm like, well, it takes the guy at the place 10 minutes to do this and it's 40 bucks. It takes me five hours. Like, what's the, you know, so I'm running the math. But so it's a skill. But it's an intentional, so you know the math.

Yeah. But it's an intentional step back for you to say, I want to grow at being more tactical and being more patient. I'm going to do this thing. Yeah. I know that this is like not a value add to my time. Yeah. But it's a value add to my sort of like emotional and mental stability and capacity,

especially as a dad. I want to be able to teach my kids things. But yeah, I definitely more of a strategic thinker. And that's why I've learned one of the things for, I think the most important thing for people like me is to find good partners or good employees that match. Because people like me tend to take it on and say, I can do everything.

And then you fail. Yeah. Because you can't, you know, I mean, you have to start alone. Everything has to start sort of alone. But once you sort of get to the nuts and bolts, being able to delegate has really helps. I mean, we're in the studio. So Nathan's basically in charge.

He and the producer. And Nathan's been with me now as my guitar player. He plays everything, piano, write songs, everything. But I defer to him most of the time. I probably, if we have 500 decisions to make in the studio, I probably go his way 490 times. Really? Yeah.

Man, I want to get to that level of trust that y'all have created within your team here in just a second. I think before we get there on this topic of vision, I heard a pastor once say that when he became a pastor, he had no idea that he would end up being incarcerated by the title that people had given him. Because he said it became a limiting belief for him that I can't do those things. I can't speak in those arenas. I can't do these other things because I have the title of pastor and that's what I do. I can see very easily how the same thing could be true for singer-songwriter. Oh, yeah.

Like I can't do those things. I'm not a business person. Exactly. and I can't start a record company. I can't start a music festival. I am a singer-songwriter. And we see a lot of times in the business world, too, people put these labels and categories on themselves,

like whether it's, I'm this on the Enigram, so I can't do that, or I'm on this on the Myers-Briggs, or I'm a creative thinker, so I can't be that discipline. You strike me as someone, I mean, even what you just said, it's like you changed the oil yesterday, right? That's not how you're naturally wired, but you did it. And you became a business person. You've stepped into these different arenas.

What gave you the ability to do that? At first it was out of necessity. I mean, when we were bootstrapping those first four or five years of touring and making records, I had to figure out all of the various things. I had to learn how to do inventory at the merch table because I was the only one selling my own merchandise after a show. Yeah. I had to learn how to settle with a promoter. I knew the deal on the front end.

And then I had to go and have the conversation and watch him do his expenses. And I remember this one time as promoter. had this sheet and he had the expenses here. And one of the expenses here was sales tax on the tickets. And then there's the total expenses at the bottom of that left-hand column. And then on the right side it said, you know, total net. And then he said, then it had another spot sales tax taken out. And I was like, you got sales tax on there twice.

You're double dipping, bro. You know? And he's like, oh, oh, shoot, that was a mistake, you know. But that was the only, I only knew that from doing that enough times. Well, that probably highlights the value of scrappy beginnings. Yeah. And so I say $348 right there, which was enough to pay a bandmate and a half. That's a huge deal.

So I don't do that anymore. A tour manager does that. But like I know how it works and I see the settlement sheet. I still look through it at the end of the next morning when he sends it out to the team. And sometimes there are things that I can pick up on because I did it myself for a long time. So I think it was out of necessity. I wasn't, I wasn't planning to learn the business. parts of it. And a lot of artists don't have to learn the parts of it because they sign a record deal early.

And the standard is you bring in a business manager and they do all the work for you. And you pay them 5% of the gross. Which people think, oh, 5% is nothing. I'm like, wait until you're grossing, you know, a million and a half dollars a year. And then if you're doing it's something right. Like that becomes something. That 5% could double you the business owners take home, you know, if they could learn how to even participate in that part of it. That's right. So it's like because they didn't learn those skills in the beginning, they potentially put a lid on them. themselves later on in their career. Yeah, and so I don't know. I think the curiosity thing, I always want to try everything.

You know, so the record club is a good example. I had joined a record club. It's like a monthly subscription thing. Dual Tone Records had one called Vinyl Den. I liked it. I liked getting a record every month. And I thought, I wonder if I curated something like this, if fans would love to see instead of a label curated,

an artist curate it. And so started it. it. I thought we'd get like 50 or 60 people signed up. And after a year, we had over 1,200 people signed up. And again, now I was like, oh, man, now I have to have warehousing space. I have to have somebody to run the fulfillment of this. Yeah, inventory. To buy records from three and four months down the road. And we don't have the cash to do that, but it's promised. You know, but it's like, so all of a sudden, like, golly, this is complicated.

All I wanted is records at my door every month. Yeah, exactly. And I wanted to, like, do that for other people. But then that one got to the point where it was like, dual tone actually was like, hey, we really love what you're doing. We'd love to buy it. And it's like, great. That's great. I'll just be a consultant on it. And so that was one of those things. I was like, I don't need to keep running this. So that's another asset, essentially. Yeah, well, it was. Yeah. I sold it. They bought it from you from you out right. Yeah. But that's a cool project that you were able to build from start to finish. And you flex some muscles and you gain some skills in that time that you wouldn't have had. And I think, too, in any business, young business owners need, like, I wish there was like a class on how money works. And you

works in the business world. We're working on it, true. Yeah, but how capital moves around and what investors expect from things and how banks work. Like, these are all things that I didn't really start learning until I was like 10 or 12 years into this, you know, and now it's really helped me understand how to make better business decisions. And it has served me as a creator because now I have more time and space to do the creating because there are less fires to fight on the business side because they're a better.

structures in place. Man, and that's a big deal. Yeah. Let's say your, you know, your business is like hardwood tables. Yeah. And you're like, man, I'll make the most beautiful hardwood tables. But if you're like, you know, out fighting fires all the time, you're not making any tables. You're not selling any tables.

Yeah. If you spend your first month doing nothing but trying to build a website yourself and bootstrap that instead of, you know, maybe paying a little bit of money. Let's see you've sold one table and you've got $1,000 in the bank. You need to build a website. Well, instead of doing yourself, maybe. be the time it takes you to build the website, you can build three more tables. That's right. Well, but it's...

But that's a hard balance to figure out. Well, it is. And it's maybe a little bit different. Drew Holcomb and the neighbors, you don't have the luxury of stepping too far away from your core competency because there is not another Drew Holcomb. Right. We see a lot of business owners that it's like, oh, well, someone else can make the table. Someone else can do this.

And they end up killing the thing that actually got them where they were because they were so busy putting out fires. And now suddenly the tables suck. and it doesn't matter how good your website is. Right, right, that's true. And that's honestly part of why I wanted to get into the record club thing. I wanted to try, I was really curious to know what it's like to be involved in a business that isn't tied to my name. Which that's a pretty big deal.

Yeah, and it was fun. Yeah. It was like, okay. Is this something you'll do again, you think? Yeah, I mean, yeah, for sure. We already have in some ways. Yeah, I think, you know, starting things or being involved. I've gotten myself involved in some other projects on the investor side.

We're not tied to my name at all, but I get to offer not only have, like, like money invested, but have expertise in the business and helping a younger business person here and there sort of get their thing going. And I'll sort of brag on this young woman, not myself. Amelia's flower shop, she has these Volkswagen drop-down vans, you know, that sell flowers all over Nashville. I think I've seen them before. Yeah. So she has like, she has two real stores as well, one on Charlotte Pike and then one down in Franklin. Well, COVID hit and, you know, she was like, we're shut down. I don't know what to do. Well, she's, you know, in her mid-20s. What are most people in mid-20s do they just go, oh, man, woes me.

I'm a victim. Instead, she goes, I'm going to really press into delivery. Let me see what happens. I'm going to reach out to all my customers. They're delivering, we're delivering, we're delivering. And she, without sharing her business, she basically did about 1,200% more delivery business than she's ever done before in the six weeks that her business was shut down. Amelia.

Yeah. Crush it. Her name's Maddie. Amelia. Well, Amelia's is a store that she went to when she was a kid in Paris. And so she named it after that. Maddie. Maddie is crushing it.

And so I was just like, you know, I've been able to be involved in her business as an investor and as an advisor. And that's been fun for me to take some of these things that I've learned and then sort of move them down the road to somebody else. Pass it on. That's too cool. Do you think you are a businessman first or an artist first? I'm still an artist first. Yeah. That's where my like I get the most satisfaction.

Really? When I write a song that I know is good. or that I know or that I hear from someone meant something to them, that's what sort of undoes me in a really good way. That's why I got into music was because music had meant so much to me. It helped me get through difficult times. It had soundtracked the best moments of, you know, music soundtracks people's like moments in their life, you know.

Good, bad, fun, ugly, all of it, you know. So that's still the most satisfying part for me is the songwriting and then being on stage. but I do really love the business side. Clearly. You know, and if it all, being able to sort of do those two things side by side and get better at both of them over the course of years has been really fun. I mean, our big pivot during this thing is we've been doing these kitchen covers. You're in L.A., correct?

Yeah, Ellie and I've been doing these covers at night. Literally from your kitchen. Yeah, literally from the kitchen. And musically, it's been incredibly challenging and great for me to have to learn a new song a day. Yeah, didn't you cover a Beyonce song or something the other? I covered crazy in love. Drew? Holcomb. Well done. Don't, don't, uh, don't dare me, you know. That's right. But y'all have been doing

Beyonce, Johnny Cash. You got all these, like, the whole gamut. And so you're learning a new song every day and then performing it that night, correct, live on Instagram. Yeah, we record them like a couple hours earlier. But then they're, yeah, then they posted on Instagram the same time every night. And it's been really fun for me to sort of figure out this, this like way to sort of add to the conversation. It's been really great for me to dive into these artists that I love and be reminded of why I got into this and how much I love it and how much I still feel like there are so many trails to walk down musically as a song or that I haven't done yet. And so that's exciting.

But then also at the same time, you know, all of a sudden we realized like, wow, people are really tuning into this. And our Instagram follower count is up like 35%, you know, which means that hopefully we get back on the road, there's 35% more people paying attention to buy tickets to shows. That's a massive top of funnel. Yeah, yeah. But it's like your flywheel, like, But the art serves the business, the business serves the art.

And that was the thing is I have enjoyed the business because I have trusted my creative instincts. So there have been times when management or label or producers have tried to deter me off of my creative path towards a different way. And I've sort of stuck to my guns. Like the kitchen covers was just a gut instinct thing. I was just like, what do I want right now? I want to play some classic songs. it'll help me sort of make sense of this chaotic moment. The kitchen sounds great.

That's where I like to write. I'll just set up a camera and we'll just call it kitchen coverage. I mean, just was like a on the fly idea and it has worked. So I have- Did anyone dissuade you from doing that or was anyone pushing those out of time? No, the whole team, when I sent the email, they were like, oh man, that's a great idea. So giving me the time and space to be the idea guy has been like a really.

Okay, but who you have these ideas, not all of them are gold, I would assume. I would assume you have some people that are like, no, Drew, we're not like, that's not a good idea. So because we see business owners struggle with this, they want to be accessible. They know there's value to healthy conflict. But then there's times where it's like, listen, I built this thing. You've got to trust my gut on this. And we just got to do this. Like, we need to do kitchen covers.

So how do you walk that line of like, okay, I'm going to let other people in and have input, but then there's sometimes where I'm going to go on instinct. Well, part of it is history. And, you know, Paul and I've been working together for eight years. Which Paul is your manager. Paul is my manager. Sorry. And Samantha, Paul and Samantha are my managers.

I've been with them for eight years. And we've had enough conflict where they've said, I know you think this is a really good idea. We think it's a really bad idea. And here's why. And I've fought them on it. And there's been times where I've done it anyways. Some of those times I've been right. Some of those times I've been dead wrong.

And they were right. And so dissecting those moments and being able to go, you know what? You're right. I'm sorry. I should have listened to you. I will listen to you next time. And so if you can bet 800 in those sort of relational things, you're doing pretty good. And so if I had sent that kitchen cover's idea to them and they said, this is a really bad idea and here's why.

And I said, well, I'm going to do it anyways and it failed. And that's on me, you know, but I have a great relationship with them. I probably would have listened. And instead, though, they're not, they're not really no people. It's like a good idea can always sort of, it's like water. like there's always a place for it to go downstream. Oh, that's good. You know, so there might be some, like, I think it's important sometimes for them to sort of tell me what the roadblocks will be.

And to maybe redirect the idea. Redirect the idea or postpone the idea or. So they're never saying, no, we can't do that, Drew. They're saying like, oh, hey, maybe that's not the best format for that. Let's try this. Or here's how this could work or what could we do to make that work, things like that. Yeah. Or sometimes there's a way to test an idea, you know, before you, before you like launch it, you know.

It just seems like you and Paul have an incredible working relationship. We do. Yeah, we really do. Like, what were the things early on that y'all did? Because you've been together for almost a decade now. Sure. I mean, how we got together is a pretty great and short story. I was on tour with an artist that he was managing at the time, kind of Ben Rector. We were good buds.

Yeah. I'm actually leaving here to go play off with him. That's pretty awesome. Yeah. So Ben and I were on tour together. It was a co-headline tour. We were sharing a band playing all over the country. And I had a manager at the time who was a great guy.

We really got along great, man of great character. But we just didn't sort of gee and Haw with how he sort of wanted the role. The hard thing about it being a music manager is every artist, the job has a very weird and nebulous title. There's not a job description. It's not a job description. Everyone has different expectations for what this individual does. Yeah, some artists need their manager to be a counselor. Some artists need their manager to be like, you know, the yes man.

Some artists need their manager to be the heavy, the bad guy. So it's just, it's all different. I needed a partner. That's what I needed. And so someone who saw the world similar to me, who could implement my ideas and challenge me. And so anyways, I'm on tour with Ben. Paul's managing him. And he's coming, he comes around to a bunch of the shows.

And I'm seeing all the work that he's doing. And I'm like, this is what I need. Okay. So in your head, though, at that time, had you identified, maybe not using that language, but had you identified, I don't need a heavy. I don't need a counselor. I need a partner. Like that's what I'm looking for.

Because that's, we see a lot of times business owners are looking for. that right-hand man. They're like, I need someone that's in this with me, that's in the trenches, but I think a lot of times they do themselves a disservice because they don't do what you did where you define, this is what I need from a person. And it sounds like your eyes were open. I did define them. Part of my defining was seeing it in an action. Really? So you saw Paul working and you were like, I need that. I was like, oh, this is what I need. I need someone who's, A, knows a lot of people in the space that I'm in and is willing to sort of inject me into conversations about touring or about festivals or about sync TV, which is synchronizations,

TV and film using music for background music. So I needed someone who had relationships with these people and who was willing to leverage those relationships in order to sort of get things done. And he had those relationships. He had been in that space with, bands and with artists who had been sort of in the singer-songwriter, Americana world. And so that was important. And then, too, he was a hustler. If there was a problem at the merchandise table and the volunteers didn't show up, he would jump in and do it.

You know, it's like, so that's the hustle I was used to. Yeah. And then also another big one for me was I needed someone who was very good at communication. Like quick response to text and emails. And even if it's not an answer, just like, I got this. I'm thinking about it. I'll write you back in the morning. I want that from.

a partner from a manager of that relationship. And he was like that because he was doing a lot of the, he was sort of a running point on the advancing the tour. We sort of split roles between my manager and his manager. And so anyways, I went to him and I was like, Hey man, I'd love for you to consider managing me. And he's like, look, I'm not, I'm not a poacher. If you have a problem with your manager in that professional relationship first,

and then we can talk. Which even that's an integrity move. Yeah. And then I was like, man, this guy really is like, you're honest also. The framework we teach here is humble, hungry, smart. Yeah. It's Pat Lindsay's humble, hungry, smart. It's like, I feel like that is Paul to a degree.

And that's what you were, you were picking up on all of those things. All those things. And so I was like, so what ended up happening in this, I did end up part in ways with my manager. I went to Paul. And he's like, look, man, I'm overwhelmed with work. Like, I've got these other three acts. We're super busy. And I said, I will be your favorite client.

And he said, why? And I said, because I know how to say thank you. Hmm. And he's like, what do you mean? And I was like, I know how to celebrate. and say thank you, you're going to love working with me. He's like, well, that's a pretty good pitch. Yeah.

Well, he also told me he said more than anyone he's ever met. Drew and Ellie Holcomb have an inability to accept the word no. It's what he said. And so, I mean, it just seems like you've got kind of, and this is part of your business background, too. Like, you've got kind of this wiring that it's like, once you decide you're going to do something, it's not yes or no, can we do this. it's how we're going to figure this out. But I assume that benefits you a lot. Yeah, it does.

I mean, the one sort of funny part about that is my wife, you know, she's always talking about how we want to have more time at home, which we fight hard for that. But it's difficult at times. But then she says, but the problem is if we have a bunch of time at home, 10 days at home, Drew's got a new idea. She's like, sometimes I just need him on the road doing this music thing. So more time at home actually creates less time at home.

I think it's one of the reason she likes it when I go play, off because she's like, I know that when you go play golf, you're just going to play golf. You're not going to come home with a new business idea, you know, or a new, even a new song idea. She's like just, you know, so it's, we definitely have clear vision. But I think we also have clear, like, things that we're like, we're not doing that. Yeah. That's what you talk about earlier. You know, it helps.

What you stand for, what you don't stand for. Yeah, it helps to sort of have, like, my big vision right now, and it's, it's a five-year vision. but I want, when our youngest is like six or seven, so he's 18 months, I want us to take a year in an RV and do 52 weeks in 52 different places. And it'll involve camping, it'll involve like seeing the world, I mean, in the United States, and do one show a week wherever we are, do a service project that week somewhere, just like really like take our kids out of this thing and have this memory that's, you know, I think six or seven, He'll be old enough for it for to stick with the baby. And Paul and I, I mean, we're already got spreadsheets.

We're working on this thing. For real. We're going to try to find sponsors, you know. Like the rocket fuel? Uh-uh. Rocket Fuel talks about how great businesses, great ventures, and even great leadership teams, they involve a visionary and an integrator. Yeah.

And it seems like, man. That's definitely seems like what Paul and I. You are the visionary and he is like, okay, like, let's get out the spreadsheets, let's make it happen. Yeah. But that's such a positive relationship that it's like, neither of you are saying, okay, that's just a hairbrain idea. You're just saying like, okay, what must be true to make this crazy thing occur?

Yeah, it's true. Now, I do, I don't want to like paint a picture that's unfair. We do fight. Oh, yeah. You know, it is. Well, that's probably part of it too, though. We fight hard. Can you talk about the fights?

Yeah, well, we'll get sideways about something and some of, you know, we both have tempers. And so those will flare. And then the other one will say, you know what? This conversation right now is getting too hot. I'll call you back in two hours. Really? It's just like, we're pushing pause. And then usually two hours is enough time to like gather your thoughts and come back with like your actual point of view or to realize like, man, I was being a punk.

I owe an apology. And we both come from sort of situations where like, you know, you don't just say, oh, man, I'm sorry about that. You say like, I was wrong for what I said to you, will you forgive me? That's where you start. You know, you don't, you don't just blow stuff past. You have to like dive into the weeds of things. And that's, that is not just working relationship. That's why I think we work together is the friendship thing.

I grew up hearing this thing from a lot of people. My dad was not this way. Other people say, don't ever go into business with your friends. And I'm like, strong disagree. Really? If you can't trust the people you work with and have hard conversations and also know sometimes when it's not good to work together anymore, then, you know, it's just a transactional relationship, which I don't, I don't have. any interest in that. I'm close with my bandmates. I'm close with my tour manager. And there is a

hierarchy on the business side on those relationships, but there's also like they have permission to come to me and say, man, like, you wronged me and here's how and why. And I think you'll have me an apology. And I have the right to be like, you're crazy. You misunderstood me or I have the should have the wherewithal to go. You're right. You know, like I'll give you a perfect example. Nathan, guitar player, runs point on our Christmas shows. Christmas songs are. so complicated. So he works really hard on him. He's recorded all the songs as a producer on them.

Last year, I got an email from some of the the guys of the 101st Army Division band in Fort Campbell. They were telling me about this, you know, just thinking me, there should be a video of them playing one of our songs. And I thought,

man, that'd be cool. What if we had some of those guys come up and play a song with us at the Skirmhorn? Oh, that's pretty cool. We're just here in Nashville. It's here in Nashville,

Symphony Center. And somehow I forgot to tell Nathan. And he's a musical director. And so we show up at Soundcheck and he's like, who are these guys? And I'm like, oh, they're going to play with us on this one song. Remember that email? And he goes, didn't send me an email about that. Guess I missed that.

And he was very calm and cool about it. And it wasn't that he didn't want to do it. He just wanted time to plan it because he likes to execute and plan over time. So he's like he wanted the right charts for them. So he's having to do that on the fly in the moment four hours before the show. That was a pretty simple song. So we were able to do it quickly. but it was not fair to him to put him in that position.

And I just messed up. And so he didn't say anything. We had a great show. He sends me a text the next day. He's basically like, you know, I put a lot of time energy into this Christmas stuff. And I know that you didn't maliciously lead me out. But that was wrong for you to do that and not let me know and just let you know it hurt. And so please don't let it happen again.

Man, that story exemplifies what it looks like to have a mature. team. Well, it took a long time. Yeah, but it's like you screwed up. I screwed up, right? And here's the deal. I had a great idea. That's right. It was killer. And it was even rooted in- But I just didn't follow through with on the communication. That's right, which I feel like a lot of business owners can probably relate to. Like, I had a great idea, didn't communicate the details very well. And there's some people that their primary priority is the details. And it's like, we completely missed that and you tick them off. But what the thing that stands out to me is you said, we had a great show. Like, he and you. And you. you both kept the customer first. Yeah. The customer won. And then on the back end of the customer winning, y'all had.

And so what was your, when you got that message, what was your initial gut level response? And then how did you respond to him, Drew? My gut level response was, oh, man, he's so right. Like, you knew. I totally screwed up. Yeah. He would have crushed writing the charts and doing it. He just, you know, I basically put him in a spot where I took advantage of him.

of him because I knew he could do it and I didn't give him the info because I was like oh he'll figure it out on the fly or at least somehow that's what happened yeah that was intentionally you didn't feel like oh I have to get it to him right now yeah you just like it was in the back of your head that my head so you know my busyness put him in a tough spot my inability to communicate details put him in a tough spot and you know he had to be kind of correcting them okay what don't you do is to play the fifth instead of the third on that note and like just you know he had to do it on the fly instead bearing. And so I just, I just called him. I didn't sense. I just called him. I was like,

you're 100% right. I'm really sorry. We're all really busy. That's not an excuse. My way of doing things caused, you know, gotten the way of you doing the job you want to do. And I'm sorry. Oh, you an apology. You know, I'd like to say that it won't happen again. Yeah. You know, and if it does, you have a right to be angry with me. That's right. I mean, we're all going to, you know, we have to screw up. We have these, you know, historical ways of making the same mistake. Governernery over. What's that called?

Pathology. You know, I have a pathology of multitasking and dropping the ball on certain things, you know, not a details person. But you own that. That's the big deal, I feel like. Can you speak to what that does for a working relationship when you screw up, take ownership, apologize? What does the relationship look like as a result or after that occurs? Trust. I think trust grows.

Because that's what we always think. And that's why we were able to do the show without. And it wasn't even that we were just putting the audience first. I think he legitimately was like he had to make a decision before it on stage. I know Drew didn't do this to me on purpose. I trust him enough to know that this was just a mistake. This was not a malicious taking advantage of me. He gave you the benefit of the doubt.

He gave me the benefit of the doubt. I would imagine resentful guitar playing probably doesn't sound very good. So he had to be up there and just like saying, like, I'm going to. audiences can feel that. I mean, like, we had one night we were doing the kitchen covers where Ellie and I had gotten into a pretty significant argument beforehand. That's a pretty big deal. Yeah, but we had to turn it in because, you know, had to remember what song it was? Yeah, I was Lerner and Fly.

You can watch it. It's hilarious. She's like playing the mandolin. She's like not looking at me, which is very uncharacteristic. She's very like in the moment, typically. And so the next day, buddy mine calls, he goes, dude, were you all in a big fight last night before you played the learning fly? I was like, yeah, we sure were. He goes, yeah.

Me and my wife were just laughing. We're like, oh, they definitely just got in a fight. So what you're saying, though, is people can feel it. Like, the customers, the fans. Sure, people know. They know. Oh, that's a big deal. You say you're an artist first.

You've got so many things going on, and it seems like your mind's always moving. When you sit down and you need to write a song, and I know that, I mean, your songs are not just marketing material. Like, you're communicating sometimes really gut-wrenching truth in your song. How do you get yourself in the headspace to really? really take that deep creative dive and write something. Yeah. I mean, I typically now have to put it on the schedule.

Really? Yeah. I mean, with three kids and managing life and, you know, all the things that go along with it. Yeah, I have to make time for it.

And then I have to turn my phone off. You know, I have to turn text messaging off, turn email off. But even that is pretty remarkable. Like, feel like a common belief is that you can't schedule creativity. I used to think that.

Yeah. What changed? Mainly children. You know, necessity. Necessity. Yeah, just life happens. You don't get to control everything.

That's one thing you just learn over time is that I don't have the luxury of just like, oh, man, I'm feeling melancholy today. I'm going to go on a four-hour walk and try to come up with some lyrics. Like, that's just not the program with three small children. And so it doesn't pay the bills. Now, that being said, I do collect inspiration all the time. you know like whether it's on mainly on my phone whether it's a voice memo a melody or whether it's i hear a song and i go man i love that drum groove i want to sort of write something similar to that and i'll shazam the song and then go back and listen to it and sort of dissect it and think how can i sort of

you know do something like that or somebody else say something in conversation and i'll go that's a good that's actually that's a great song title and i'll just save it and then you know the scheduled time is when i sort of gather all those things i've collected and try to build something out of it you know so it's like you're always sort of treasure hunting in your normal life it's kind of like a growth mindset too it's like your eyes are always open eyes are eyes open then I also have some practices like I get the Sunday New York Times and I try to um about twice a month I'll get out a piece of paper and it's really it's like a journal but it's not it just to basically use it like a like a pad and I try to collect a hundred words and phrases so I just you know let's get out the

the travel section and just like fine words and phrases that just stand out yeah they just are interesting you know it's like yeah you know you could just anything you know john so and so was walking down the street with his dog when he was interrupted by oh interrupted by interrupted by and you'll just do that every sunday not every sunday but yeah it's a practice for you though when i have the when i yeah when i'm and so interrupted by is that a song title or is that something you write based on you just you just say like that strikes me i'm going to pull that out. Yeah, it just strikes me, you know. Yeah, I'm trying to think of like, I'm trying to look around the room here. So, uh, fight for the mission, you know, let's say that's like you find that somewhere.

Yeah. In an article, they go mission, mission, okay? And then now I'm going to find eight words that rhyme with mission. So I'm going to Google mission, rhyme zone, you know, mission, vision. And then you go soft rhymes, you know, so you kind of like, I always say the enemy of a, of a new song is a blank page. So you got to start with something. Wow. You know. So I never sit down with just a pad and go, okay, universe, hit me with it. What's striking me today. Yeah, I just sit there and stare at the page, you know. So whether it's a melody idea or some words, that's sort of how it gets me going.

The other thing I do, this is my greatest trick for songwriting is I'll print off the lyrics to a famous song. Let It Say The Beatles Let It Be. And then I'll write new music to it. It's like not the let it be music. Really? So I find a different key, change the tempo. Same lyrics, though. Same lyrics.

And then I'll record that. And then I'll flush, then I'll get rid of the lyrics. And now I have a musical structure and a melody, a totally new melody, that I can then write words over. Is there any song that we know of that you've created as a result of that practice? Yes, for sure. Fire and Dynamite. Really? Yep.

Do you remember what song that came from? Yeah, it was a version of Silent Night. Are you serious? Yeah. So you wrote the lyrics of Silent Night, you wrote new music to Silent Night, and then you took away the lyrics and then just wrote, shut up. And it became Fire and Dynamite. That's Fire and Dynamite. Unreal.

I'm trying to think of a business parallel over there. Well, I mean, you know, I think every good idea has a sort of, I'd love to hear, like, how the sort of seltzer water companies have created their thing in the last few years. I mean, you know, they've taken this re-skinneding old ideas, you know, there's not, there's certain ideas that are not copyrighted, you know. We get the idea, I think, that we have to create something original. Yeah. It has to be brand new. It has to be original.

If it's not original, it's not business, right? But it's like, what you're saying is like, no, we start with Silent Night. Like, that's a really old song. Yeah. But then we just use that as the base level to create something new. Yeah, it basically just helps me create a structure to then build. Because I find sometimes that finding, like, new music is harder than finding new, new words. You know, most artists are songers would probably say the opposite, but I have a harder

time sort of, because I'm also not like a super prolific musician. I can't just like, I don't play by ear. I can't just like pick up and play anything. I'm sort of limited to the Johnny Cash calls it the sort of three chords in the truth mentality. Now it's not exactly that, but finding new musical sort of a new musical skeleton is helpful for me, you know. When you think about the impact you want your music to make, on people that listen to it. What is it? Hope that holds on to suffering. I want my music to push

people towards love and courage, but not just for the sake of love and courage, but out of the truth that life is hard at its most meaningful when we're honest about the difficulties, sadnesses, and failures that we've experienced. And that's how we can actually live a life of love and courage is to be honest about the pain in our own lives and the pain around us in the world.

You know, I want like a song, like, See the World, a song about my son. I want people to hear that song who are parents or who have important relationships with nieces and nephews or godchildren or whatever, for them to look at those kids and feel hope and aspiration for them, but also be aware of the sadness that, like,

man, my kids are going to grow up and they're going to experience pain and suffering. And that's part of what it means to be human. And that's okay, and I can't stop it. And I'll be here for it. them when they need me on that ride you know and so that's what music's been for me it's also you know part of that whole thing is just is it's okay to have fun it's okay to dance in the kitchen that song family yeah that you do with your family it's killer that you've got some moves drew

like the music video that's pretty impressive no one of the reason i want to do is people i'm sort of stoic on stage um dry no smile kind of personality and uh but i do like to have a good time I like to dance. So I thought, I'm kind of surprised people here with some. It worked. Some of my late 30s white guy moves. To do what you do at a high level and continue to do it at a high level seems especially demanding.

I mean, I've heard you talk about this newest album, Dragons. And like some of the songs on that album just seems like it must have been a pretty intense journey for you to walk through. Yeah. I mean, you know, we've talked about how do you know when you're, keep going when to quit. I mean, I had a moment really in 2017, we're almost quit. Really? Yeah, so not that long ago, you know.

And it's not because the career track wasn't working at that point. The career track was working. Yeah, sort of. I mean, honestly, that was part of it, was the career track was working, but I had gotten too aggressive in expecting growth and we got ourselves into sort of some financial trouble on a tour. That was not the main reason I was sort of like thinking about quitting. It was just like it was so exhausting. to put so much sweat and life and your own sort of story into these records, and then to feel like they're not connecting the way that you want them to or enough to sort of cover the nut,

and then to be out on the road and to be feeling like that particular tour, the music wasn't connecting as well as I wanted it to, I could just feel that in the audience. When you're on a tour with a new record, you want people to be singing the new songs back to you. That communicates like, oh, all I could feel from the room was they wanted old songs. and I also had gotten really sick in December of 16. I was in the hospital for nine days of meningitis.

My word. And that typical joy that I was talking about earlier being on stage, I wasn't there because I was just beat up physically. And I was missing my wife and my kids. And I was just like, this is too hard. I just cannot keep this pace. And Paul and I figured out some ways to sort of like draw back. I ended up sort of doubling down on my songwriting.

I usually would write like 20 or 30 songs in a period of like three or four months before a record. And then I don't write really much at all for like a year. And instead I wrote two to three days a week for 18 months. So the options of songs was a lot more. And then I'd co-wrote a lot and co-wrote with other artist friends. Like I wrote the song, Dragons with Zach from the Lone Bello. I wrote with Natalie Hemby from the high women. You know, I wrote with Lori McKenna, it's, you know, award-winning singer-songwriter and friends of mine who had met over the years that said they'd want to write together.

So I was able to sort of like do new work. And then two songs sort of rose to the top, family and Dragons. And those were really personal songs. And so I realized, okay, this is going to be a record about sort of dealing with the many hats that I wear. And then everybody wears when they get older. I'm a son. I'm a husband. I'm a father.

I'm a grandson. That's what Dragons is about. You know, I'm a business owner. I'm a musician, I'm a songwriter, all these different things, and it's complicated, you know. And then the song, like, maybe was this sort of dealing with a personality of, like, the song of the chorus is maybe you're not supposed to try everything.

And it was sort of me coming to the limits of the end of my sort of ambition and aspiration and wanting to see and really the whole Carpe Diem thing really hit home with me as a kid. Like, you know, she's got take on the world. Do all of it. Do all of it. And all of a sudden you realize, like, I'm not going to do all of it. I'm not going to climb Mount Everest. I'm not going to maybe ever climb any other mountain.

I'm not going to drive a race car. I'm not going to fly a fighter plane. I'm not going to visit every country. I'm not going to learn four new languages. All these things that you tell yourself, I'm going to do. And you go, you know what? I'm actually not. And that's okay.

So this record was me sort of wrestling with all those things. And so all of a sudden it was like, yep, this is going to be the most personal record I've ever made. And my favorite part of that story is, A week before we went in the studio, Paul sends me this email. He says, hey, man, none of my business. And you can tell me to jump in a lake. A little more colorful than that, but we'll keep it. Appreciate that.

Keep it safe. You can tell me to jump in a lake, but a lot of your fans don't know the story about your brother. It's not in your music, except for this song that's not even released anymore. I always want to encourage you to write a song about that. just now's the time this record is the right record for it. What he didn't know was the night before I'd been walking home from the post office and I had this sort of daydream vision where I was, it was dark outside. It was a night and it's really cold out.

It was January. So I kind of swept into this moment and my brain sort of took me back to the gathering after my brother's funeral. Which was how many years prior? That was in 1999. So that was 20 years. Yeah, 20 years. Yeah, because I sent the song.

And I went home and wrote down what this vision, this song was, and it's a song called You Never Leave My Heart. I had not sent it to Paul yet. So I had written it the night before. And then he sent the email. So I just wrote him back to email. I said, go jump in a lake. Oh, by the way, I wrote this song last night. And he called me like 45 minutes later.

He's like, I don't even know. I can't. The song is so good, man. But I just let myself go there in this record in a way that I haven't before. Is it hard? I made a vow to play that song on the tour, and I think I played it 90% of the nights. I don't think I'll probably ever play it again. It was like the moment in time for that tour, I'm going to play the song live.

And people kind of knew it was coming. It's not one I can really, it's like a pretty intense song about loss. Oh, I heard it. Oh, yeah. And then Nathan's guitar solo is just like, I mean, everything about it sort of came together in a really sweet way. Why do you feel it's so important that you take that stuff from your experience and share with others? Well, the great thing about being a creator in today's world is that you get a lot of feedback from social media, which can be a bad thing. Yeah.

But mostly it's good. And I get stories, when I told that story and released that song, I think there were like 900 comments from people who had lost someone close to them. And they were like, I don't have the words. I don't have the language to express what that has felt like for me, but you just nailed it. I'm forever grateful. That was the public comments. Then the private comments, there were probably another 500 with much longer and sometimes

more intense stories. And so I told Ellie, I was like, hey, I need about 24 hours just to read all these. I want to read everyone. I wouldn't able to respond to all of them, but, you know, people have been through hell, you know. Like people on your podcast who are business. owners. A lot of them have been to hell and back for various reasons, whether it's losing somebody or burying a dream or, you know, and I think people need art, whether it's music or film or paintings to help them make sense of their lives and to make sense of the losses

and the wins and the love found, the love lost, all the sort of like tensions that life has. So if I can offer that to the world, then that's what I want to do. That's what I'm trying to do. and that's my hope. And sometimes it's as intense as that. And other times it's as silly as me dancing with my children in the music video and family. And those two things are of the same truth. That goes back to that hope and suffering. Yeah.

So that's sort of my, when you say, what do you want people to take away from music? I want them to take away that they're not alone. Life is complicated and difficult, but it is also totally worth living. So you're going to play one for us today, which I'm pumped about. If it's cool with you, we'd love to hear dragons. Yeah. So can you give us the story kind of behind this song? And then I'd love for you to tell also the story of you premiering this song.

I think it was at the Symphony Center here in Nashville. So this song was written with a friend of mine, Zach, Williams for the Lone Bello, and we were talking about our grandfathers. I grew up five doors down the street from my grandfather. He was a surgeon. In World War II, he was a doctor. He lived in Tokyo after the war and operated on the war criminals union. It means like crazy stories.

He played college golf. He golfed all the way through his whole life. He was an itinerant preacher at Baptist churches on random Saturdays and Sundays in North Mississippi. He was a taxidermist. He had a whole North American game bird collection. He just this giant personality of a man, like the big fish kind of stories. Where you're like, that didn't happen.

And then you go find out. You're like, yeah, it totally did. I mean, he might have embellished it a little bit. Larger than life. Larger than life figure. and really lived life and really loved people. I'm one of 28 grandkids, and we all felt like we were his favorite.

You know, I probably went fishing with him 40 times, hunted with him 50 times, played golf with them a dozen times, watched him do taxidermy every week. And he also loves, like, you know, his Bible study leader, he taught me how to, you know, read the Gospels and just was just like incredible man.

Had his flaws, for sure, but everybody does. So he died 15 years ago, and Zach and I were talking about how our grandfather still sort of like, in a good way, sort of haunt our being. You know, like they inform who we are. We carry them with us. And so we wrote this ghost song. This is a song about encountering the ghost of my grandfather on a camping trip.

And it's a simple sort of classic, in this sort of simple classic country mode. And we debuted it in 2018. We did the Christmas show at the Skirmarhorn. And it's not all Christmas music. It's about half and half. And so with this one moment, we bring out this old,

it's called a Myrtle mic. And it's just us around one mic. And it's Nathan on acoustic, me on acoustic, Rich on upright, just the three of us. So this is that moment that you're talking about when you talk about loving to be on a stage.

Oh, this is like, this is picture perfect. Picture perfect. So I said, hey, y'all, we're going in the studio. In a couple weeks,

we're making a new record. It'll come out later next year. This is a song I wrote a couple days ago that's going to go on the record. I hope you like it. Play the song. Well, start the song. After the first chorus, standing ovation.

In the middle of the song? In the middle of the song. Has that ever happened to you before? Definitely not. I mean, I don't think I've, you know, I think maybe three times in my life

I've gotten a standing ovation in the middle of a show for anything. Is there a recording of this? No. Oh my gosh. I mean, it's all in our, for the people who are there. It's recorded in our memory.

But yeah, so we got all stage and we're like, that's a great show. And I said, Well, I guess the name of the new record is Dragons. I'd say so. So this song has been a really important one for me. It's been, I think, the band and everybody.

It's now one that if we don't play it, we're in trouble with the audience. There you go. Well, it's one of my favorites. And we're going to share it with y'all today. He was nice enough to bring the guitar in studio. Here is Drew Holcomb's performance of Dragons. I was climbing a mountain. Sleep in the moonlight.

A ghost of my grandpa came to me in a dream As the stars hung above us He started singing this chorus He laughed loud as heaven He said this to me Take a few chances A few worthy romances Go swimming in the ocean

On New Year's day Don't listen to the critics Stand up and bear witness Go slay all the dragons That stand in your way We stayed up and talked until the sunrise Of war and love and sorrow He said stop spending all your money

On forgiveness of sins Today is all you promised Don't trouble with tomorrow He faded in trouble to the forest, proudly singing this hymn. Take a few chances, few worthy romances, go swimming in the ocean on New Year's Day. Don't listen to the critics, stand up and bear witness, go slay all the dragons that stand in your way. I woke up with a fever surrounded by lightning.

All my windows are open, and I let the rain flood in. The past felt like the present, with a future uncertain. I sang like a sparrow lost in the wind. Take a few chances, a few worthy romances, go swimming in the ocean. on New Year's Day Don't listen to the critics Stand up and bear witness Go slay all the dragons

That stand in your way Go slay all the dragons That stand in your way Go slay all the dragons That stand in your way Well my goodness How on earth do you follow that he is just so good at so many different things.

It's really quite inspiring the fact that he doesn't put himself in a box and he's still growing. He's growing as a business owner and as a leader and as a father and as an artist. He's still pressing into new arenas and trying to expand his capacity and he's like really serving other people in the process as well. I love the lyrics from the chorus of that song. It says, take a few chances, a few worthy romances, go swimming in the ocean on New Year's day. Don't listen to the critics, stand up and bear witness. Go slay all the dragons that stand

in your way. Well, if you're like me, that song is going to be on repeat for a very, very long time. And one of the coolest business applications that came out of that conversation, there were so many of them, but I think my favorite was that story that he told about him and his guitarist Nate and that conflict that they really had right before they went on stage for a performance in front of hundreds of people. I just thought it was so cool to hear about how his team, his band, handled that in such a mature and healthy way. And that's what we believe here at Entree leadership. We believe that teamwork is not the absence of conflict, but rather great teams are built on a foundation of healthy conflict. That's why our team created a free resource called the Difficult Conversations Checklist. And what

this does is it walks you the business owner through some of the tactics and principles that you need to make sure you build the skill of handling and leading through difficult conversations that will inevitably happen on your team. So if you want to get this checklist, I want you to text the word difficult to 3344. Again, that's the word difficult to 33444 or just click the length that's in the show notes. Well, I hope you enjoyed this episode of the Entree Leadership podcast. If you did, please give us a five-star review and tell your friends to subscribe. For a chance to win a $25 Amazon gift card, you can review this episode by clicking the link that's in the show notes. And be sure to follow us on social media at Entree Leadership.

This episode was produced by Tim Hull, and it was edited and mixed by Will Rudder. I'm Alex Judd, and on behalf of the entire Entree Leadership team, thanks for listening. We'll talk with you again very soon.