30 – Jonathan Freeland: Art with Impact

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0:00 Jonathan
Learn to find joy in the tough moments and have patience that you're going to end up in one of those high points again, but the lows don't always have to be “this is the end of the world” and they don't have to be compared to someone else's high points. Just because those people are on Broadway doesn't mean that they didn't go home and have their ceiling flooded or something. We all have these things happen. So I know that you say keep your eyes on your own paper. And even now, I have to do that.

0:39 Tony
Hello, it's Tony Howell and I want to welcome you to Conversations with Changemakers. In this month's episode, we have a very special guest, Jonathan Freeland.
Some of you may know Jonathan as my longtime associate, but he is best known as a musician and songwriter in Nashville, Tennessee, but you may not know is his full artistic and entrepreneurial journey from early training at the Cobb County Center for Excellence in the Performing Arts to professional training at the Joffrey Ballet School and Point Park University.
After graduating and working in musicals like West Side Story, Million Dollar Quartet and Carousel, Jonathan was always writing music, and performing with bands. If that wasn't enough to keep him busy. He was also constantly focused on developing one of his many creative skills: photography, graphic design, website design and product design, including his now shelved but delicious Day Dreamer Coffee Company.
I wanted to have Jonathan on to speak about creativity, particularly sharing some behind the scenes on releasing his genre breaking “Emo Country.” He released his first solo EP, Young & Proud in 2018, and the title track was placed at the top of Alternative Press’ “New Alternative” playlist on Spotify. He has since released 9 singles featuring artists including Less Gravity, and Kevin Jordan of This Wildlife, and a self produced live album and live stream.
This is literally my right hand man, and I cannot wait to hear your thoughts on his wisdom, Enjoy!
Jonathan Freeland! Oh my goodness, I'm so excited to have you as a guest on the podcast. Thank you for being here.

2:40 Jonathan
I couldn't imagine being anywhere else.

2:43 Tony
It's 6:30 in the morning in Nashville. So thank you for starting your day here. I know a little bit of your story. But I know that our audience knows a little bit as well. But we want the full T! So I know you're a Point Park graduate. And I know that you spent some time in musical theatre, but you are a singer-songwriter in Nashville. So tell us about all these different paths along your way.

3:08 Jonathan
Sure. So I grew up in a not really I wouldn't say a creative home. My parents are creative people, but they would never label themselves as creative. So I didn't grow up in like an artsy kind of environment growing up, but I was always interested in singing, and I loved going to see shows whenever I was a kid, we would go to the North Georgia State Fair. And there were always bands playing there. And so that was like a highlight. And so I grew up around a lot of country music. And kind of though I didn't really hit my stride as a performer until I would say high school.
I auditioned for a performing arts magnet program, and that really just opened a world that I never even knew existed. I went for an orientation and took ballet for the first time. I was like, “What is this?” And so coming from a very athletic childhood. I was like, alright, well, I don't know what to do with this yet. It's really interesting, but I'm gonna keep singing. And then we'll see where it goes from there. And then the dance bug bit me.
So I went into that school, they had majors and minors sort of like college as a vocal major and dance minor—ended up flipping that on its head. And the summer going into my junior year, I ended up doing an intensive in New York at the Joffrey Ballet School where I'd gotten a full scholarship.
So the training at that high school was really intense. And it ended up I mean, there were times where I thought, how do people do this? This is so crazy, but it really really prepared me for the craziness that is the musical theatre business, especially in New York.
So I guess, really, like going back to that school—having that sort of really rigorous education with the arts. I learned that it's not just about like, oh, I want to dance, I want to sing, that it has to be very focused. And that left a really big impression on the way that I really continued my life on.
So I did four years there: singing, dancing, acting, all of that stuff. And I didn't really know what I wanted to go to school for my senior year. I knew that I liked performing, but I still wasn't sure if musical theatre was going to be the thing. And this is where like, I love my parents, they're very, very pragmatic. Because I was having a lot of, I don't know what I want to do, I kind of want to be a songwriter, because I still love that whole thing. And my parents were like, “Well, why don't you try out musical theatre for college, because you get a degree in three very versatile skill sets. And if you go and you decide you don't really want to do that, then you can hone in on whatever you want to do.”
So I think having, I mean, this is what I love about my parents, is anytime that I get in the artistic struggle, they're like, well look at it this way, try looking at it from this frame, and they can kind of bring me back down.
So yeah, went to Pittsburgh, and the four years really kind of flew by now like thinking about it. It's all a blur. And maybe that's just after having been out of school for so long. But combined…
You're still young.
I am still very young. Yes, almost 32. But it was at that time that I really feel like I started figuring out where I was going to fit in “the biz.” And I knew that I really, really loved dancing. I still enjoyed singing, but it was more so that I wasn't as enamored really with, like, singing for musical theatre.
I had a lot of friends, obviously, like the circles that I floated in, because I went to shows a lot while I was in Pittsburgh, and made a lot of friends with people in bands. So I started being like, “Okay, well, maybe in my off time,” because I definitely and I'm sure anybody that went to school for musical theatre or anything creative has their ups and their downs. And I remember very vividly having a massive like bummer after a class where I just felt like, if I'm no good at this, I don't know why I'm even trying. I was like, let me just start writing songs. Let's see if that's the creative outlet. Because I love playing guitar. I love playing covers, but I'd never really honed in on, I wonder what this outlet could be like. So my sophomore year of college, I wrote a five song EP with a very loose “band.”
And it was not very good, looking back in hindsight, but it was exactly what I needed at the time. And like, I got to go into a studio and record. And it really lit this other fire where I was like, oh, man, because it's really not the same. And I'm sure we'll dive into this later. But like performing on a stage theatrically and performing onstage in a rock band are two very different energies, and in many ways, very different ways of connecting with an audience. And so I think I was really trying to figure out, like, I know that I want to connect with an audience, but how can I do it the best way?
So after those four years, I really kind of dove into New York and said, okay, cool. I had really no money. I was a terrible saver whenever I was in college, so I had just enough money to get there. It was like $1,000 in a suitcase and a guitar, the classic story. So I paid my rent. And this was like before all of the job finding websites were up. So it was like, trudging Craigslist for serving jobs. And that was, you know, like, I guess bouncing back and forth on a couch for that first week.
And I ended up getting a job and was working in the Meatpacking District with which I thought was really cool at the time. I could never imagine waiting tables in the Meatpacking District anymore. But I was there. I was in the city, I was making money, and I could audition. And about a month after that, I booked the national tour of West Side Story as a replacement swing. And to be fair, I did have a little bit of practice because whenever I was in college, I was going up on the Megabus every couple of weekends it seemed like those last few months for this exact audition. So I already knew the choreography. But I had been put on sort of the waitlist at the end of the audition. And that was really crushing, because I was like, I wanted to have a job right out of school. But I am a firm believer that things happen the way that they're supposed to happen when they happen. And it's up to us to figure out how we're going to respond to it.
So it ended up working out even better because not only did I get the job, but then I didn't have to worry about housing whenever I came back afterwards because I was able to sublease my apartment. And the transition was very smooth. So I guess that's another experience that felt like college 2.0 on that tour because it really was a continuation of great, here's what you learned.
Nothing can prepare one to be a swing. There are people that are amazing at it. I think I was okay. But I did enjoy it: really it was a rush. I've never felt unsupported. And I learned a lot about how to manage stress on stage. Never had any huge accidents, which was great. But that experience was really, really amazing.
So yeah, after I got back from that, I kind of toiled back and forth between auditions and working in restaurants and worked regionally for about, I guess it was like the next three or four years. And it was around that time, though, where I really was starting to have those, like the highs were high, and the lows were super low. And there were so many lessons that I learned there artistically in those lows when I wasn't working, that ended up really feeding that fire of okay, you don't have to wait on someone else to determine your career path as an actor.
And it was right after I believe this was in 2017 or 2016, I was swinging a production of Million Dollar Quartet. And I was just like, man, this is kind of marrying both worlds of the songwriter, the musician, the actor. And I was like, okay, well, I'm going to take a break from all of this. And I'm going to just dive solely into songwriting and doing my own stuff. So I kind of put a non-official hiatus on auditioning and jumped into full time entrepreneurship.
That was whenever I started the Day Dreamer Coffee Company, which was really cool, because I got to meet so many other people as a result of that. And it was truly this is something that looks cool. I'm going to learn everything I can about it, and just jump in. And so I had a partnership with the Lululemon Men's store down in SoHo, so I got to do pop ups there, and was really just looking at every sort of creative/collaborative thing I could do.
And it was right around, this would have been a little bit after us, because I can't negate whenever we met, that would have been 2016, I believe. And that was right after I had done a production of Carousel. And I came back with a bit of an injury (not related to the show), and was like, I want to find something that I can do that allows me to work while I'm auditioning. And I would be remiss if I did if I didn't say that it was a massive part of allowing me to explore that creativity. So I cherish our time together, I'm sure I'll say it a million times over the course of this interview. But really, once I started working with Tony, it really was like a whole new world. Even in digital media.
I kind of knew how to build websites, but I wasn't very good. And I mean, our work together has, I think, not only brought me a lot of creative fulfillment, but definitely a lot of technical expertise has come along with it. So if you're watching, you're listening, and you're working with Tony, you are in good hands.

12:54 Tony
I paid him to say that.

12:58 Jonathan
But yeah, I guess, to fast forward even further: 2018 was when I put out my first full fledged EP. And it really was… it was an experiment. I knew that I loved country music from growing up with it. I listened to it my whole life. But also in those teenage years, I had a lot of inclination towards I think I wandered into a Hot Topic around sixth grade and found these punk rock CDs that were like $2. I was like, “Oh, what is this music? What is this whole thing? And who are these weird kids that I enjoy hanging out with?” So there really was this kind of dichotomy through not just my friend groups, but in my music taste. And because I felt like, okay, I'm old enough to sort of discern the best of both worlds, why don't I try to make something that's authentic? Because that was really what I felt was missing for me in the theatre world was, there's a lot about, you need to be authentic. But sometimes it's hard to live that out. At least it was for me—to not really type myself into things.
So I put out this EP, and it ended up one of my favorite alternative music magazines placed it on their Spotify playlist. I was like, okay, well, maybe something is happening here. And so I promoted it, and just kind of felt the waters, I guess I didn't really know what to do. At that point. I was still new. I didn't know anything about distribution. And then I put together a band through I was like, I don't really know enough people in New York that are musicians. So I got on Facebook, or on Instagram, started asking around and started playing shows with a group of a couple guys that I had just kind of met through the internet.
And that's kind of been if there's a theme of my artistic life that's sort of, it is like, put it out on the internet and the people that are meant to come will come and I still play with these same guys every time I go back to New York. So it's become a really wonderful friendship.
I would say probably 2019 or 2020, right before the pandemic hit, I had finally gotten in a financial place where I was like, okay, I can make music, I'm gonna be good now and started putting out singles. And then when the pandemic did hit, it was a struggle to say, “Okay, well, I'm not going to be able to perform here anytime soon. What do I do?”
And at the time, right before COVID hit, I had met my now fiancé, Katherine. And during that time, we, I mean, people talk about like their COVID relationships, their COVID marriages, you really get to know somebody really well when you're stuck with nothing else to do but talk to them.
And we said, I was like, “What about Nashville?” My parents live down there, and her parents were from Indiana. So I mean, obviously, places were super cheap. I was like, well, let's do it. And if we hate it, we can always come back.
We obviously didn't hate it. We're still here. And I think getting out of that really crazy environment helped open up a lot of brain space creatively. And that's where if you've seen anything about me recently online, most of that was born from the time that I moved from New York to here, because I just had time to focus in on. “Okay, here are my ideas, how can I execute them in a way that makes sense?” Instead of “I'm doing 6 million things, oh, I have to do this, oh, I have to put out the song. I should be doing all of these things” versus “Okay, here's work time, here's music time, here's personal time.”
And really, the last biggest thing, kind of where we are now is in 2021. I was watching a live stream while we were snowed in here, one of my favorite bands and was like, I would love to do something like that. And I was like, why can't I? I mean, I know people, and New York is shut down. So I'm sure that there are venues that would allow us to rent out their space. And very long story short, I got a venue that was way larger than I ever thought I could have with a five person camera crew, the band that I love playing with, and we were able to record a full concert. And because I only have so much money, I was like, well, I'll take it back and I'll edit it, which took about a year. But these were like lessons.
I was talking to my artist coach about the recap of this project: what would you do differently? It was like, I would hire an editor. I DIY’d that one when it wasn't necessary. So that's the beauty of DIY is you learn those lessons firsthand, and things improve quickly.
But, uh, we were able to raise about $200 for a charity that I'm really passionate about called Sweet Relief Musicians Fund. And it was something that I knew that, great, I want to put on a show. But there was something very much attached to wanting to do that. It's like, yes, of course, I just want to perform. But I want to make sure if I'm wrapping up something in a big project like this, that it's about more than me. And that's really where I would say the theme of what I've realized that I'm trying to do artistically now is that, obviously, yes, I want to write songs that speak to me, I want to write songs and speak to people, but I want to make sure that there is a positive impact through what I'm doing. So I don't know how many times I said long story short, but it was a very long story.

18:12 Tony
It is! I mean, I did my research a little bit. But now I know the full Jonathan story!
I want to connect some dots. One of the things that I saw as a through line is your, I will label it as fearlessness. But I also like the way that your parents phrase that as trying things on like, just go do it. And then you can always go a different direction.
I think oftentimes, artists and entrepreneurs are scared to take the first step. So I applaud that. And then your resourcefulness. You figure out the resources, the means, the way once you've taken that first step.
And finally, the last thing that I heard was, it's about more than you. It's got to be about the audience.

18:52 Jonathan

18:53 Tony
So I love the twists and the turns: all of the different hats. If you could go back in time, here at 32 and speak to 22 year old Jonathan, fresh out of college, what life or business advice would you give to the young artists?

19:09 Jonathan
I would say that patience is the number one thing to practice. I went through a lot of my younger years feeling like I should know things that I didn't know yet. And I was at times very afraid to ask questions, because I didn't want to be looked at as dumb. And so I think having patience and being willing to ask questions are super super integral, especially at the high school / college level. But even whenever you get to New York, like, is this a company I should audition for? Is this a class that's worth going to?
I think that patience really ties into those ups and downs. Like I feel like I learned a lot more about how to be truly happy in those lows rather than whenever I was, you know, up on stage, because whenever I was there, I was doing what I wanted. I felt that creative fulfillment, but really sitting in those moments where like, I mean, I still think about this one very vivid time that I was putting a glass rack up at a restaurant and it slid down, and water just fell all over me. And the glasses all broke. And I was like I have, I have friends that are on Broadway right now singing, and I am sitting here doing this, what in the world is going on?
And then like, I would get home and be super exhausted and be like, why am I doing this when I feel like I am meant to be doing something else? And now, knowing what I know, that there's a lot more of those instances, I guess proverbially in life that are going to happen, then there are going to be the highs, and really, it makes the highs that much better.
So I would say, learn to find joy in the tough moments and have patience, that you're going to end up in one of those high points again, but the lows don't always have to be “this is the end of the world.” And they don't have to be compared to someone else's high points. Just because those people are on Broadway doesn't mean that they didn't go home and have their ceiling flood or something. Like, we all have these things happen. So I know that you say keep your eyes on your own paper. And even now, I have to do that.
If there's that person, that is always the person that you compare yourself to, and you find yourself going back to their profile and social, it's okay to mute that story every now and then. Not because you don't like them, but because if it doesn't serve you, if it's bringing something negative, then it's okay to cut that out. You just have to be able to do what you gotta do.

21:45 Tony
That's brilliant advice. very tangible. So everyone, go start muting. Let's talk about the cities just for a bit. Many, many, I don't know how many years in New York City, and what did it teach you.

21:56 Jonathan
So it's been about 7 years in New York. And it taught me how to focus because you have to focus whenever you're there. There's so many distractions, there's always a million things to do. So I really had to compartmentalize my time and know that, okay, here's how much time I need to dedicate to making money so that I can pay my bills. And here's how much time I need to dedicate to making whatever the next thing I wanted to work on was. And like, I felt like I was already pretty disciplined coming out of college. But the way that I learned to think about creative work in New York was so different because of the time and the space constraints.
So it wasn't like I could just go off to a dance studio and not spend money. It was like everything. I mean, I paid for it in college, I'm still paying for it. But it wasn't as easily accessible. So I tended to think that, okay, here's my day-to-day life, here's my day-to-day job. And I need to treat the artistic work that I'm doing and entrepreneurial work that I'm doing the same way. Otherwise, it just never will never get done. So I used to write in my calendar, like, here's where this is. And then here's like the second shift or the night shift. And then as I started making the transition from service industry work and performance work into entrepreneur work, I would find places in my schedule for both of those two things, and I would slowly start to replace them. So I would cut back hours at the restaurant, but I would take those hours and fill them with, okay, I'm taking a class on this, or I'm getting on YouTube and I'm going to learn how to do this in this time, which helped me not stay up until three o'clock in the morning, every night. But I think the biggest thing that it taught me was that if you want to do something, you have to do it yourself because everyone is running around doing their own thing. And if you don't care about it, then you won't ever be able to convince someone else to.

23:58 Tony
So much there to unpack, but I actually have a curveball for you. And fun fact for our listener is that Jonathan went to Bali first before I did. And I was like, what is this? I want to go! So what did Bali teach you about life?

24:13 Jonathan
Well, I made a solo trip there. I'd never been outside of North America. And it actually taught me a lot about slowing down as I'm sure you've experienced. It really is a much different way of life there. And I went there to go to a fight camp. So I was expecting this very like, boom, boom, boom, I'm gonna go and experience all of these. I don't want to say aggressive but I mean like fighting is an aggressive sport. So it was going to be a very action-filled type of vacation, while also going to the beach on the off days, but it ended up being the exact opposite.
And I met these guys who really, I mean, they fight people for a living, but their demeanor was so calm and chill. And I was like how do these guys do this that they can for, you know, an hour and a half at a time become this savage fighting animal and then right as soon as that's done, okay, let's go to the beach or let's go to the bar and just hang out.
And so many of the guys that I met there just have a very kind of lax view of life like, we're only here for so long. So like, why not do what you want to do, and that I would say that I might have missed in my artistic journey.
It really was a pivotal moment for me as a songwriter, because I had put out a couple singles prior to that EP release. But I really wasn't motivated to continue writing or, or anything like that, and being over there, and really just like going to class and then coming back and doing a little bit of work and listening to music and being out on the beach. I was like, man, I only get to do this once. So why am I spending my time busting back and forth auditioning for things that I don't really care about necessarily, instead of just doing the thing that I know brings me a lot of fulfillment. And I'm sure we'll touch on it later. Like, it felt like much more of a vocation to be exploring this part of myself artistically than I ever felt in “the biz.”
So for me, I was like, I really need to hone in on this and being out there in a completely different timezone, I didn't have any excuses. I didn't have any distractions. I had to sit with those feelings. And it was fantastic. I recommend it. 100%.
Anybody that wants to go to Bali, you should go.

26:24 Tony
I have a guest room. And we have to… Yeah. All right, let's talk about Nashville. How long have you been there? What is that like? How has it changed you?

26:33 Jonathan
I've been here for about two years now. And it has absolutely slowed me down a lot in the best ways. Like I said before, I have much more brain space to be able to act on these creative urges and ideas now than I did whenever I was in the city. But it's allowed me to really, I guess, appreciate things that I may not even have appreciated. Had I come here before I went to New York, like, I'll take our dog Beverly on a walk every morning, and more mornings than not, I'll just look at the grass and trees and be like, Oh, this is like a vacation. And in many ways, because when you're in New York, and you get outside, it feels like you're on summer vacation. And then you come back for the school year in New York. And now it's kind of the opposite. It's like going to New York is like an exciting vacation to the museum where I know I'm gonna get to do all these, see all these amazing things, and meet all my friends. And then I get to come back. And it's a little bit of a slower pace. So I would say it's taught me to appreciate things that I might have otherwise thought were monotonous. And I don't know how much it's necessarily changed me artistically. Or maybe even personally, I think it's just allowed me to discover other parts of myself that I didn't even know really existed, or appreciate things that I would have never appreciated previously.

27:55 Tony
One of the things that I appreciate about you is every time I ask you to get on camera, or film something, is that the background always changes. So I feel like we are in your studio right now: a space of creativity.
And you and your fiance are making a home there. But uh, you know, I love to find the parallel between this physical world and the digital world that we live in. And you've created a gorgeous website for yourself, JonathanFreelandOfficial.com, you're helping create our gorgeous new home, TonyHowell.co, you create for all of our clients. I could drop them all by name, but that we would be here forever. But okay, so when you're creating a space, whether in person, real life, or online, what do you think about in terms of putting that together.

28:41 Jonathan
So efficiency is the word that I like to use across the board. But obviously, they're two very different mediums. And I guess for online spaces, I want to make sure that a people enjoy their time there. But more so. And obviously, that it's beautiful, and it has that wow factor. That's super important.
But my main goals from an efficiency standpoint are that they have a good experience while they're there. And that they want to come back for what the next thing is. So I always try to design an online space with those two elements in mind: that it's a fun experience to be there, and that there will be some sort of hook to get them back. Whether that's, you know, the email capture form, or even advertising any of that kind of stuff.
But I want to make sure that it's a reflection of me: that people feel comfortable sort of inviting them into my digital home, as we say, for our clients and decorating, or I guess I would say creating a physical space, really until I got to Nashville, I had never live really lived in a space that I could 100% make my own.
When I moved to New York it was the first time I lived in a room by myself, not in like, a house, because I lived in doubles the whole time I was in college. So that was an interesting experience. But I think what I've learned about how I like creating spaces, physically, is that they need to be efficient, but more so in the sense that they should be efficient in getting me where I need to be, when I'm there.
So for this space, it needs to be efficient at getting me into a creative space. So I love being in like, by these spaces, I knew, Okay, cool. This is what I need to create for this space. In the kitchen—much different. It doesn't look like this at all. Because from an efficiency standpoint, if I can't cut a vegetable without cutting my hand, then no one's getting dinner. So I try to make sure that when people come over that it is an enjoyable experience. However, my main goal isn't necessarily to keep them coming back. It's more so that it needs to be able, I guess my physical spaces are a little more selfish than my digital spaces.

30:55 Tony
Well, I'm definitely ruminating on this idea of efficiency. It's like, I like that we'll have to add that into the classes and things.

31:04 Jonathan
Yeah, yeah. Because I think efficiency gets kind of mixed up in the business world of efficiency and synergy and everything. It needs to be efficient so that it can get done faster. And the way that I tried to think about efficiency is does it get to the end goal? Does it put me in the place where the end goal was met faster, but not just for the sake of being fast. It's like this space is efficient at putting me in a brain space that I can write good music, so it's a good space.

31:32 Tony
Efficient and enjoyable: the Jonathan Freeland experience.

31:38 Jonathan
That's going on my announcement bar.

31:41 Tony
I love it. Let's talk about music. So you have released both an EP and most recently a live album. You and I both know that there are many of our clients that have already released music or they know that they want to do it. They just know there's a Christmas album or original music or something. So what is your advice to them about releasing: even a single or a full EP?

32:08 Jonathan
So don't rush the first release, that's the biggest thing. Once you do your first release, you put yourself on a bit of a timetable, not that you should rush any of these things. But once that first release is out, you're going to want to make sure that you have follow up materials and all of that. So I would say take all the time, you need to plan that first one, no one's going anywhere.
Don't get stuck in paralysis, about figuring out the perfect way to do it. But you want to make sure that you have something I would say at least one or two follow ups before you put out that first release.
I learned this from doing it the exact wrong way. So learn from me. But I think the other big thing is, once that first release is out, it's okay to play with… allow it to be a jumping off point. You don't need to have created that whole brand. And then say, for the next five songs, it's got to be this brand. So allow the audience reception to inform you. And it doesn't need to change what you're doing. But it's something to take into consideration: how do people respond to it?
And if you get any feedback on anything, be able to parse out the constructive from the negative. Because once you put something out, it's the same way as a review in a theatrical show, you're opening yourself up to that. The years of no in the audition room will help you be able to navigate any of those bad reviews.
And I personally had a music video premiere that was placed on a publication that ended up getting overwhelmingly negative reviews on that publication, the comments section was pretty vile. But it ended up kind of just being like, this is so weird that something that I made made people feel something that strongly.
And that was what I was able to come out with was okay, if I'm going to make something then I want to make sure people feel something about it. So that's another big lesson in creating, in writing music. is if you're going to write background music, or music for a commercial, or an elevator, that's one thing if that's your intention, but I would say like really try to know what are you trying to say? And is it going to elicit emotion from your audience?
So that's, I guess, a little more philosophical than the technical but the other technical stuff is, you want to make sure you have all your bases covered because a lot of new musicians think the song is out there. I have the song recorded—great. I need to find a distributor—great.
Now what my biggest pet peeve as a listener and as a consumer of music is whenever album art is boring or halfway thought through or it feels remedial. And it doesn't matter to me whenever I get that new music Friday playlist. If I see album art on there, it doesn't matter how good the song is. I've already made an impression. And I know that we talked about this with wine labels. Like you see you align with, it could be the most beautiful wine, but if it looks like the label was just slapped on there, you may not go for it. And so that's where I would say that is the next most important thing to the music being polished. Make sure that your album mark or your cover art creates that environment that the song is going to be playing against.
And I personally love working in Photoshop, it's one of my favorite things to make next to writing music, is the merch, and the album art. So make sure that you take some time and maybe like researching on I think it's Behance. You just type in album art there. There's tons of stuff that even if you're not a designer, you can take to an artist and say, here are my thoughts. This is sort of what I'm thinking. So definitely don't skimp on good cover art.

35:53 Tony
I want to highlight one thing you just said because it's something you know, I'm teaching business, whether it's to clients or in the coaching program, and this idea of feelings and emotion.
It's why in musical theatre, like we dance when we can no longer speak, but it's why people make the purchase for the $10,000 handbag. So I liked that idea. And I just want to put neon lights around it is like once you have your intent, really make sure that you are tapping into the audience's emotions. Brilliant advice.
Well, speaking of emotions, let's talk about “Emo Country.” Tell me about, I don't know, pick a song and give us a little bit of behind the scenes! Maybe highlight some lyrics. But what should we know? Which song should people be aware of?

36:37 Jonathan
Yeah, and it's funny because it's really like the first one that I think still speaks to what the project is, “Young & Proud” which was really the first song that I've, personally still love, that I created from scratch. And that song was a lot about my artistic struggle. And the one that I feel like ended up connecting with the audience the most from that release. And I remember writing the bulk of it, after a very long double shift on a Sunday at a restaurant and just being like, I am totally worn out. But I can't imagine doing something else with my life.
And at the time that was being an actor, being a performer in the theatre. But I think I was really starting to understand that, oh, this is artistic life in general, not necessarily right into the theatre world.
But I mean, the process has changed a lot over the years. My first couple songs were recorded in my New York apartment on like a Yeti snowball mic. And I was working with a songwriter and producer based just outside of Chicago, and I would record all the instruments and I would send things to him. And somehow he did a lot of magic and made things come out really beautiful. So that partnership also informed a lot of that sound and kind of where the project ended up going.
But like I touched on in the first part of this interview was that I wanted to find something that married both of those worlds and felt authentic to me. I've loved a lot of aspects of country music and rock music, specifically in country music, the stories and how the lyrics and the stories were at the forefront of those songs. And were really like just vignettes about real life. And with the rock music a lot of times I guess for me because there were a lot of themes in some of these songs that were very heavy growing up, and I didn't come up in a particularly traumatic childhood, that it was a lot more about the emotion that the music itself gave to me and as an angsty teenager. Like those banging guitars and drums and everything. I was like, oh, this is exactly how I feel, even if I don't really connect with the lyrics per se.
So I wanted to take what I thought were the two things that spoke to me and mash them together because I didn't really see anybody doing that on a large scale at the time. And it ended up evolving from this sort of rock project with a country flair whenever I was writing “Young & Proud” about honestly being an angsty 20-something trying to figure out like being broke. And just knowing like, I can't really do anything else or I won't be happy.
That has been I think the through line of a lot of my music is that there are all kinds of things that the world's going to throw at you. But as long as you know, kind of where you're supposed to be, that you should keep doing that. And the world's going to bend eventually. Well, I guess you could say either the world or you is going to bend eventually.
And in the song one of the lyrics is “I might hate it now, but I'll never call it quits.” And that's really how I've tried to continue on with this. Like being a musician is very difficult from a financial standpoint, just because of the way the industry has changed. But it's up to us to evolve and we talk about that a lot. You can complain about things being the way they are, or you can evolve with it and find a way that makes it work for you.
Trying to think of any other song in particular. I mean, I love the most recent single, but it was 100% like I wrote it for my fiancé. I do love it. But...

40:16 Tony
What is that song?

40:17 Jonathan
“Out Last Time.” And I mean, I guess what I could say is, the project also is… if you were to listen to my discography in chronological order, A.) would love you forever, because that's cool that somebody would do that. But there is a through line, if you were to listen to my most recent song versus “Young & Proud,” or even “Summer of ‘10.”
There's a lot of difference in themes about where I'm really prioritizing my life. And obviously, that comes with getting older and changing cities. But the one thing that really I feel like defines this project is the stories are always meticulously crafted, sometimes too meticulously, and I always want the music to marry that story, which is a direct, I mean, that is directly from my training in theatre.
So if I didn't have that theatrical, musical analysis training, I don't think that I would be able to write songs. I personally think that I write good music, obviously. But I don't think I would be able to do it in a way that makes sense to me. Without those years of knowing how one marries the other.

41:22 Tony
This is like kind of just reflected back to you. It's like one of the things that I love about branding and web design is that we are creating an experience for people and telling a story. Rather than becoming a character, I'm like, “Okay, who do I step into? And how can I help them get to their objective? What tactics are we going to use?”

41:41 Jonathan
Yes, absolutely! Being specific, I guess this could be another thing for new songwriters, knowing exactly what story you're trying to tell—what emotion you're trying to, like, what is your tactic? Who are you speaking to? If you have that theatrical training, your first couple songs may not be where you want them to be. But they might be a whole lot better than if you didn't have that sort of ingrained knowledge in the back of your head.

42:03 Tony
Everything comes down to human experience. Speaking of humans, you and I have many behind the scenes chats that people don't get to listen to. But we've helped people launch books, albums, podcasts, websites, but Jonathan, you mentioned it, you love designing merch, and I gotta say that your merch is off the charts. I've seen it also elevate, but I'll also connect the dots. And finally, you had a coffee company for many years. So that was maybe the beginning of creating products. And now you have products that go along with your music. So I feel like I know the answer to this, but I want to hear your answer. But like, why is merch important and how do you go about creating new merch or your music?

42:42 Jonathan
So the dry business answer is it's free advertising. I try not to think of it that way. And if anything, my merchandise does sometimes the exact opposite of that, because I put my name so small on everything.
But for me, the merch attached to, specifically in the rock world, the emo world, the pop punk world, that like Warped Tour world, the fashion and the merch was such a big part of that. And a big part of why I initially got interested in it, like I was into the music, but I was like, these t-shirts are so cool. Like, I want to wear one of those things.
And it also really ties into like, how does it make somebody feel? Does it make somebody feel like they are putting on something that allows them to communicate what they're feeling? And so I guess whenever I'm designing merch, it's another artistic outlet for me, like the coffee company was something where I could go completely outside of the performance world and just try on a branding thing was something else that I like. And this kind of allowed me to focus that in a little bit and say, like, I want my songs to be statement pieces, and I want my merch to be statement pieces. So musicians will often think like, I need merch. And they'll maybe go and get somebody to design something with their name and a really big font, and maybe a graphic and call it a day. Whereas for me, I wanted something that the 15 year old me would go to a show and be like, I need to get that so that I can wear it to school the next day because it's so cool. And it speaks to me.
So like, most recently, I put out a crewneck that just says “Emo Country” in college... it's like a collegiate sweatshirt. My college experience was extremely non-traditional. So like, I didn't have college merch. I didn't go to college town. So these are things it's like, I always wanted one of those cool like collegiate sweatshirts, so I made one and somebody walking around with a sweatshirt that has my name on it. They'd be like, Okay, well, whatever. And I've worn this out whenever I go out in public, I wear all of my own merch because I didn't only design stuff that I would want to wear. I've had more people ask me what that is. And it starts that conversation. And that's really one of the things that I learned in the music world is you want people: the word of mouth is extremely important.
So if people are excited about “What is emo country? What even is that?” Then I've done my job with the merch. And the upside is I personally love the design. So I want the songs to elicit emotion. I want the merch to elicit emotion. I want people to feel things.

45:16 Tony
That's brilliant. And I love the free marketing. But I think some people might be intimidated. So you and I both know that it's been lucrative for some of the clients. But would you be willing to share like percentages of how much money you make from the music versus how much money you make from merchandise?

45:32 Jonathan
Of course. So you'll always make a bigger cut off of your merchandise across the board. CDs are a bit of a dying medium. So I personally don't print physical copies of my music. Streaming rates are, I guess they're depressing, you could call them depressing. We'll go back for another like thing for new musicians is thinking about music is a little bit different than it was 10 years ago, I like to think of whenever I'm putting a song out, that's much more of your marketing effort, the song is marketing to get people to buy your merchandise and come to your shows.
As far as how much money you're actually going to make off of it, because really, streaming music doesn't make a lot of money. So I would say from like, in my world, the pie chart would probably be maybe 10% of it is music sales is where things come from. And then I would say maybe the next 40% would be merchandise, the last 40% would be live shows. So I'm terrible at math, but it's close to a 50:50 merch and shows.
Music really is a discovery tool. I know there's a lot in the news in the artistic world about like, we need to up streaming rates. we need to up streaming rates. And yeah, that would be great. But my main goal was always to get people to come to one of my shows. So for me personally, this was never like, I mean, I love writing songs. I love recording them. But I love being on stage and connecting with human beings. So all that taught me was just a mindset shift. Like you write the music to get people to discover what it is that you're doing, so that they can come party with you, wherever it is that you're going to be playing.

47:13 Tony
It's lead gen! It's the same thing with authors as well. The book, Seth Godin calls the book is the souvenir—they come see you, hire you to speak, or take your online class or what not.
Yeah, yeah, you juggle so many things, a life and business, but you've been in many different industries: theatre, music, design, photography, which we didn't even touch on photography.

47:34 Jonathan
I know! How could we forget?

47:37 Tony
What have you learned about being a healthy CEO? You mentioned some things: I love how you schedule your days when you are making transitions. But what other tips do you have to be a healthy CEO?

47:49 Jonathan
The biggest thing that I've learned? Burnout is real. So organization is key. And that’s not to say there aren't times to burn the midnight oil, because that is part of any CEO’s journey, you will have to work longer hours until you get to the point where you want to be and then you probably will continue to work a lot. But I heard a really great quote that every good thing in life comes in moderation, including moderation. So you want to moderate how much you're having these extreme bouts of work and resting. But you also don't want to live in the middle, you want to make sure you are still having these peaks and valleys because you want the peaks to be exciting. So if you feel like you're super comfortable, and you're trying to change something in your life, then maybe it's time to turn up the volume. But if you're feeling burnout, it's okay to lower it for a bit.
And I would say if you're doing something that sets you on fire, you are going to have those peaks and valleys but you'll enjoy it. The valleys will feel more like learning spaces. Because I personally, like I didn't have any financial backing, whenever I started my artistic career, the only way I was able to learn all these skills was because our county had a magnet program.
So like my mom, in order for me to take dance classes outside of school, was working second jobs, my dad was working second jobs. So when I got to New York, it was really like, “You’ve got to do this or you're gonna go back and live on the farm and who knows,” and I really didn't want that.
So I would say like, also know what your anxieties are. For me personally, like in my 20s, a lot of it surrounded money. I was always worried about running out of money. And so I know that in the entrepreneur world, there can be this sort of looking down upon people that will keep a salary job. And I know this happens in the artistic world too. It's like if you get a salary job, then you're giving it up, you're doing the corporate grind.
Salary jobs are not what they were in the 80s. It's not showing up to a cubicle and then going home and doing it 5-6 days a week. I know for me, I enjoy having a salary job and it allows me to have the work that we do, it allows me to have a little bit more of a focus whenever I'm in there. So that I'm not worried about being off, but I need to also be looking at these 600 other freelance things.
At the same time, whenever I know where my next meal is coming from, that frees up a little bit of artistic space. So figure out which way makes the most sense for you. And don't let the outside opinions about how people think that your journey should be going affect you.

50:33 Tony
Brilliant and you handle it well. You're always so calm and collected. So one of the things I wanted to pick your brain about was your advice…
What's different about marketing, like we talked about the business and different industries, but in terms of marketing yourself as a singer/songwriter in the music business, versus how the actor/singer/dancer should market themselves in the theatre business? What's the same, what's different?

51:01 Jonathan
Yeah, most of it overlaps. I would say, like, I have more material to work with as a songwriter, just because I own almost every single piece of it. So I'm not bound by copyrights in the same way.
And I would say like, my voice is a little bit more loose than it was when I was auditioning, just because like, I want to still remain professional online, but it's okay for me to be a goofball every now and then, because it's my project. I'm not reflecting poorly on somebody else necessarily.
So like, obviously, I want to make sure I'm all good. I tend to avoid controversy online, just because I enjoy human to human connection on certain aspects. So I would say like, from an artist standpoint, or like from a songwriter’s standpoint, I like to focus everything online, in marketing about like really focusing in on that.
And then I would say, the biggest difference is that there's definitely much more personal outreach necessary as a musician than there ever was when I was an actor. Because as an actor, when I was marketing myself, it was much more about, here's the show that I'm in, and it was me sharing what it is that I'm doing. Here's the show that I'm in, I'm touring, it wasn't up to me to sell tickets to that show, there was a marketing team out there selling tickets to that tour. So it was just me, sharing my life with people. And also, you know, dropping the hints at any potential person that was looking to hire me, like, Oh, he's out doing this, he's doing this, he's doing this. So that was an intention.
But now that I'm not necessarily looking for the next show, I'm not trying to set myself up that way. I'm still trying to drop hints to the people in the industry that I want to see what I'm doing. But there is so much more DMing involved and emailing and all that. Because if I don't sell tickets to those shows, nobody comes to them. Do not ever rely on a promoter or a booking agent to get people to come to your show, especially in New York, this last show that I did here this past month, then you did some promotion, had I not gone and made a list of all the people that I wanted to see while I was there and reached out to them, it may not have been as successful.
So I think that there's a much more hands on approach necessary to marketing and social until you know, you sign your multi-million dollar record deal. And you can have somebody doing all that for you.

53:31 Tony
But then you're still CEO, you just get to outsource a little bit more.

53:34 Jonathan
Yeah, you get a nice little advance that you'll have to pay back eventually. But I think also, learning that and knowing about it will save you tons of headache and money later on down the line. Because if you do outsource, and somebody's not as good as you were, you can, at the end of your contract, gently say like, “Oh, this was great, thank you. And I'll let you know whenever I have another project,” and then you do it yourself.
Again, that doesn't happen to me very often. But it's always good to know the ins and outs. It's like owning a restaurant. If you don't know how to fix the dishwasher, and your dishwasher is broken at your restaurant, you lose money, and nobody is happy. So I guess, have a finger on the pulse of what's going on all the time.

54:18 Tony
Well, you mentioned that you don't like controversy. But one of the things that I see that I appreciate and I'm grateful for is that I see you as an ally to many communities. And you and I know that I look at artists as changemakers and that's why you're on the show my friend. So any advice on ways that you practice being a changemaker or an advocate or an ally?

54:41 Jonathan
Yeah, I would like to think that the biggest part of my personal purpose on planet Earth is to make a positive difference. I know that's why we ended up being put in the same circles. I know that that's your goal as well. And I guess the only… the real way to explain it is there's a concept.
I mean, I grew up in a pretty, I wouldn't say rigorous, like Catholic household. But my parents were both very, very devout. And one of the things that we learned growing up was, I mean, like, there's a lot of talk, I think, in the world. And I'll probably get esoteric on this, I apologize. But there's a Greek term called agape.
And I know in Christian circles, people talk about it a lot. But I think that concept for me is how I try to approach any person that I am working with come into contact with, because translated to English, it's unconditional love and charity.
So there are no strings attached to any aspect of whatever it is that somebody's going through. If we disagree on something, A or B, that does not mean that I'm not going to treat you with love and charity. So I can't personally say that I can understand everyone's viewpoint or experience, because I can't, there's only so much that I can truly understand. But what I can control is how I'm able to respond to somebody that comes to me in need.
And I always tried to make sure that I am meeting any challenge for any issue with grace and charity, because I mean, we're all human beings. So it does me no good to pick and choose who I'm going to be nice to, for help. And I think being willing to understand what somebody's going through is a massive part of that. So even if somebody is coming to me with a problem, and I'm like, I've never personally experienced this, what I can understand is that it's something painful for them. And I can always, at the very least give an ear.
So I think the biggest way that I found to kind of put that into action, like this is a great concept to love everybody. Okay, awesome. Like how do you formulate your days, your life around that?
There was a concept that was brought up to me in the last year, I believe. And it ties in so perfectly with the theatrical world. For anyone listening that's familiar with Hamlet, there's a device used in Hamlet called a metadrama, or it's the play within a play.
And I was learning about theological things. And heard of this idea called between the ego drama and the theo drama. So in a theological sense, you have your ego drama, which is your day to day the things that are concerning you. And then you have the theo drama, which is the story of the universe, what's happening, how is everyone intertwined. Learning how to take myself out of that ego that day to day and understand, okay, here's the purpose of the universe, here's what's happening in the grand scheme. If I'm overly consumed with my ego, and what's serving me, and that I'm the main character of my own story, it doesn't allow me to really see how much good I could potentially do for other people. And so shifting that off and saying, yeah, my day to day is going to happen, but I'm not necessarily concerned with, okay, great, I got 100,000 streams on that song. Okay. But somebody came to me with an issue, and I was able to, at the very least listen to them, maybe help them think through it or resolve it, that holds a whole lot more weight, because that reverberates and I think it's the same to tie it back to Hamlet, if you went to see Hamlet, and you watched that play within the play, and that's all you watched, you'd be like, “Man, this was a really boring play, I really don't understand it.” But that small scene in the context of the greater play makes so much more sense.
So understanding what the big picture is, I think allows us to do as much good as we were possibly meant to do. I think that, and I know that we've talked about this before, that there's like a divine calling for every person on planet Earth. And I think it's up to us to know what that calling is.
And if we're stuck in our ego on the day to day, it makes it really difficult. Maybe we'll hear glimmers of it. But if we're focused on the bigger picture outside of our own personal selves, I have found for me that those glimmers are a lot more frequent.
And sometimes it's harder, because it's like, oh, this doesn't, I don't feel like this is serving me. But I personally believe that it's not really about me, it's about what can I do? How can I take the graces I've been given and act through those or have all of my actions reverberate up?

59:50 Tony
Well, I love that. I think that's beautiful, and it's gonna keep reminding me to practice that mindfulness… to zoom out. But the theme of this show is using your work to change the world, and I thank you for being a part of my company, for helping me help all the artists that we do. And I thank you for also being your own vessel, your own channel and creating so much beautiful art that makes people feel things. So any last bit of advice for the artists, what do they need to be reminded of?

1:00:18 Jonathan
Everybody's life has a specific divine plan. And all we have to do is be receptive to it. And I think if you set goals as if you're attempting to be an expert at everything that you try, you're going to be really great at what you enjoy doing. And you'll know very quickly, whether it's something you do or don't want to do.
And the biggest thing is to not be afraid to pivot whenever you're doing something, and it doesn't serve you. So I think that with all the ups and downs in our personal lives, we'll never really know for sure what our legacy will be. But the one thing we can control is the impact that we leave on people.
So as long as that's a positive impact, we're in a good spot.

1:01:04 Tony
Thank you, Jonathan Freeland, for the impact that you have had on my life, my business, and our community. And thank you for listening.
Now, I shared quite a few things that stood out to me within this episode. So now, I'm curious to hear from you. What stood out or spoke to you? Take a screenshot and share your biggest takeaway, making sure that you tag Jonathan Freeland and Tony Howell so that we both can see it.
Now if you want to go further, check out the link in the episode description because I have curated a shrine to Jonathan, including his top tracks, latest merch, his incredible live stream, and more. And if you're so inspired, you should go check out JonathanFreelandOfficial.com. I promise it is a very efficient and enjoyable experience.
Can I ask a quick favor? Please take just a few seconds to rate and review this show on Apple Podcasts. It really helps other people find out about the podcast. And while you're there, you can check out some of our past conversations. And make sure that you subscribe because there are incredible changemakers ahead this season.
Once again, thank you so much for listening. And now I ask that you go out there and use your work to change the world.
I hope you and I have a conversation about that very soon.

On this episode of Conversations with Changemakers, we speak with Jonathan Freeland.

While some of you know Jonathan as my long-time Associate, he is best known as a musician and songwriter based in Nashville, TN.

What you may not know is Jonathan’s artistic and entrepreneurial journey: from early training at the Cobb County Center for Excellence in the Performing Arts to professional training at the Joffrey Ballet School and Point Park University. After graduating and working in musicals like West Side Story, Million Dollar Quartet, and Carousel, Jonathan was also always writing music and performing with bands.

If that wasn’t enough to keep him busy, he was also constantly focused on developing one of his many creative skills: photography, graphic design, website design, and product design—including his now shelved but delicious Day Dreamer Coffee Company.

I wanted to have Jonathan on to speak about creativity—particularly sharing some behind-the-scenes on releasing his genre-breaking “Emo Country” music. He released his first solo EP, “Young & Proud” in 2018, and the title track was placed at the top of the Alternative Press’ “New Alternative” playlist on Spotify. He’s since released 9 singles featuring artists including Less Gravity and Kevin Jordan of This Wild Life and a self produced live album.

This is literally my right hand man and I cannot wait to hear your thoughts on his wisdom! Listen to this episode for insights on:

  • Make shifts and transitions in your personal life and artistic career.
  • Creating art with an impact: production, packaging, and promotion.
  • Balancing self-care and activism: ways to reframe success and time on the daily.

Click here to access bonus resources from this episode.

Connect with Jonathan Freeland:

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If you enjoyed this episode, leave a review on Apple Podcasts. Be sure to check out our past conversations and subscribe for next month’s special guest!

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