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Music-Preneur Mindset Podcast Suz Paulinski Rock/Star Advocate Judah Holiday

#85 | Music-Preneur Spotlight: Judah Holiday

Less control & more trust make for beautiful art.

Learn why it’s not necessary to start with Split Sheet Agreements in order to establish trust in a collaboration and how Miami-based singer-songwriter Judah Holiday went from solo artist to team player after taking care of his mental and physical well-being.

You can give yourself your own record deal and say, ‘I’m going to allocate $1,000 a year to my music career,’ and that’s a recording contract for yourself.

You’re listening to Episode 85 of the Music-Preneur Mindset Podcast.


Hello! You’re listening to Episode 85: Music-Preneur Spotlight: Judah Holiday.


I’m your host, Suz – a mindset coach helping music professionals get clear on their goals and find the time to get it all done, as well as the permission to get none of it done in exchange for time to process this new normal.


In honor of May being Mental Health Awareness Month, I felt my conversation with Bronx-bred and Miami-based singer/songwriter Judah Holiday was particularly meaningful to share with you at this time. We discuss everything from the importance of self-awareness to the importance of structure and having the support of a team when it comes to staying healthy and focused on your goals.


Judah, in addition to crafting infectious pop music laid over hypnotic beats, writes deeply reflective lyrics with unflinching honesty about his life experiences. His single, “Good Life,” a nuanced, piano-laced track with an inspiring sunny disposition, was sparked from a 2018 stint in rehab. You’ll hear more about his journey with addiction as he shares with refreshing candor what he’s learned about giving up control and having more patience.


Judah and I also dive into how he learned to trust collaborating with others and how he made the shift from strictly a solo writer to someone who collaborates often with others, most often with his co-writer, Kevin Rudolf – a singer/songwriter/producer known for his four-times-platinum hit “Let It Rock” and manager, Josh Snyder.


Judah’s music, no matter the collaboration, remains rooted in a classic sense of song craft largely inspired by James Taylor and Neil Young. I highly encourage you to check out his work, including his latest EP, Young Hearts, and lead single, “Choke,” under Paperclip Records. Links to all of his channels can be found in the show notes, www.therockstaradvocate.com/ep85 and on his website www.judahholiday.com.


In the meantime, enjoy our conversation about authenticity, transparency, and what life is really like signed to a label.


Suz: So everyone, welcome! I’m here with Judah. Judah, thank you so much for taking the time to be with us today!


Judah: Thank you so much for having me!


Suz: I’ll try not to hold it against you – I know we’re both New York born and raised and you did leave us for Miami, but I won’t hold it against you.


Judah: I appreciate that. It was something I had to do, but everybody’s got to do their own thing to stay centered, so that’s what I had to do.


Suz: Absolutely. I’ve definitely been there myself, as our listeners know. If you could tell us a bit about your start in music and kind of where you’re at today.


Judah: Well I started playing the drums at around age 7 and I’ve always had this desire to continue to learn and play music, so that’s what I did throughout my childhood. It turned out that I was not a great student, I did quite poorly in school. Music was something that needed to be a career because it just came most natural to me.


That’s why I never stopped pursuing it despite my failed grades and at times – like I got thrown out of a college for having bad grades – it was just not good. Throughout that whole time I would just continue to write and record music, and I went through so many different phases of writing styles and making melodies and a lot of them were not great but when I moved to Miami in 2010, I started getting into dance music just for listening pleasure and then I think a lot of that stuff got me inspired to write more melodic hooks and different things like that. I think that’s a large part of why I have the sound I have today.


Suz: I love that you brought up the fact that maybe school wasn’t your thing but music gave you an outlet. Was there a particular aspect of it, I know you mentioned finding dance music – was it the melodies and the instrumentation or the lyric writing or a mixture? What do you feel spoke most to you that allowed you to express yourself in a way that maybe school didn’t?


Judah: Feeling a catchy melody is so satisfying for me that it’s just not comparable to anything else. That’s really what I love most about music – is that feeling that I get when I hear pleasant sounds.


Suz: I’m always says so in awe – my listeners know I’m not a musician by any means and for artists like yourself who are able to hear that, to get that melody, or to get that inspiration for a hook or a beat – I’m just always in such awe of how people can experience certain expressions through music is such a beautiful thing.


And then you’re able to share it with all of us, which as a listener, I’m always very thankful for. I know you collaborate often with Kevin Rudolf these days but when you were first starting in music was it something that you kept to yourself? Or did you have a group of friends or collaborators that you worked with? Was that experience like?


Judah: So for a very long time, I wrote alone and I was very against writing partners just because I didn’t know how to deal with splits and different things like that. I was always caught up in the wrong things like who has the most percentage? And it was just a bad thing to be sort of obsessed with, but at the same time you hear so many different stories about people getting cut out of songs that I ended up focusing more on the writer shares before songs were even complete and it was just a terrible hole to get into.


Only when I moved to Miami did I start really collaborating with individuals that really enhanced my songwriting. There’s something alleviating about not being alone and relying on yourself anymore. It’s just something now that I kind of don’t like doing. Now it’s trying to give this song the most respect as possible and bring in and utilize the appropriate people so the end result is as good as it could be. Then worry about this splits later, and so far there hasn’t been any issue ever.


Suz: Yeah that’s a really great point to bring up. We’ve spoken a lot on this podcast about as you become a music-preneur, understanding things like splits and royalties and copyrights and protecting your music, but I love that you brought up that there’s a middle ground that you have to find because as you said if you get too carried away with, it can really take the fun and the trust out of that collaboration.

I’m glad to hear that stepping back from that and focusing on the partnership that you’ve found that you can trust that in people that you’ve chosen to work with. I think that’s really great to hear. Do you have a process for that in terms of determining who you collaborate with and choose to work with or is it just like this gut instinct that you get in the moment? What has that been like?


Judah: So now-a-days, I have a team that I worked with. So Kevin Rudolf is one of the members and my manager Josh is a really great songwriter, so I generally will bring my songs to them, and the three of us really wrote my entire album. I’m open to writing with anybody that sort of shares similar interests to me and music styles. The goal is to write good music written by people who are motivated to write that good music.


A writer might have a chip on their shoulder and can be unpleasant and then you just sort of leave the session – you’re not required to stay. I guess because of my personality and my openness to really talk about my feelings, shortcomings, or positive things that have happened, I’ve had a very good experience with the people I’ve worked with so far.


Suz: I love, as a reminder to other artists listening, you can leave. That was such a great point to bring up that this is supposed to be art and expression and if you’re not feeling that, there’s always a respectful way to do that, you have permission to be in charge of your own choices.

One of the things we talk a lot about on this podcast is feeling empowered to make your own choices, and I think that’s wonderful that you feel empowered enough to say this isn’t working for me and if beautiful, wonderful inspiring art, whether it’s meant to be happy or sad – or whatever emotion it’s meant to emote – it’s there to inspire people and to connect with people and you can’t really do that if you’re not connecting with the people you’re creating with, so I love that you brought that up.


And you had mentioned just a bit ago about your team with Josh and with Kevin, and I know that Josh Snyder is your manager and you are currently signed with Paper Clip Records, again a lot of our listeners, for them their goal, this brass ring to get signed, to get a label deal to have a team… what was that journey like for you? And is that what you were going after – did you always want a label deal? How did all that come about and what was that process like for you?

Judah: I spent 15 years writing and recording music and submitting music to all these different online services – there are many places online that will say they’ll help you out and sometimes it’s scammy, sometimes it’s real but the way that I got signed was Josh and I were next door neighbors and I invited him over one day and it turned out he was in a touring rock band called Atomic Tangerine in the early 2000’s and they had a decent following.


I had no idea. When I played in some of my songs on my guitar he really liked them. Not every song was ‘a hit’ but is every hit a fan’s favorite song? No, also. So I had began begun working with him, and we just started writing together a little bit and we love each other first of all, he’s like my older brother and is a cancer survivor and the type of guy who’s like ‘Let’s just do this! I believe in it’ and I never heard that from somebody before.


I always craved to hear something like that from someone because all I’d heard in the past was, ‘If you give me this, I could do this for you’ or, ‘If you pay me this, I’ll be able to do that for you’ and I knew that day will come where it won’t be so much about money but rather this fire burning inside you of necessity needing to do it. We were working together for almost a year and then I met Kevin because I bought one of his older guitars. I ended up buying that guitar deliberately to meet meet him and play songs in front of him, I didn’t need the guitar.


Miraculously he enjoyed the music too and then when me, Josh and Kevin got together we began sharing that music. And we were able to find a local indie label here Florida that was very interested in putting the sole focus on me because they believe that the merging of my story of addiction and life experiences, plus the music I was putting out played a nice role in today’s world because it’s just all honest.


It’s not about wearing a cool necklace or dying your hair red, not that I could because I’m bald, but it’s the best set up that I could ask for and things are really moving in a positive direction. It’s really crazy how it happened.


It’s hard to believe and it’s hard to sort of identify the moment when things went from, ‘It’s not serious’ to, ‘It is serious,’ but over the past year and a half we’ve just been going extremely hard, pushing my songs out and amassing almost 2 million views on YouTube. The reality is that’s not a lot at all in the grand scheme of things unfortunately, but it’s a starting point, and that’s just the craziest thing that on their own time they chose to listen to my record.

It’s a very great feeling and I always thought I wanted a record deal. I always thought that a record deal was the holy grail of music and that’s the end of whatever, but the reality is that a record deal is the following: it’s an investment in a person, just like real estate as an investment in a person.


That’s all that a record deal is , and you could do that at whatever scale you want. So you can give yourself your own record deal, and say I’m going to allocate $1,000 a year to my music career and that’s a recording contract for yourself.


It’s important to know that it’s really not more than that. I know it’s hard to envision that when you don’t have it, but I was that guy that would sit in my room staring at the mirror playing my songs pretending like I’m on Jimmy Fallon’s show that night and thinking about how I’m sitting in my green room with a Bologna platter and all that stuff, and it’s not like that at all, especially now.


Suz: I want to thank you for shining a light on that because it’s something that I think it’s just innate for independent musicians, especially given how difficult it can be to see yourself as a music-preneur, you know you guys don’t get into this so that you can be a business person, some people take to it more easily than others, but you get into it for the music. You get into it for what those melodies in your head did for you when you weren’t doing well in school. You get into it for the feeling that it gives you.


And so when you when you’re ready to take it seriously, and you add in all of this business stuff and all this left brain, not-so-sexy, not-so-creative stuff on top of it, it can get overwhelming and the thought is, ‘Oh well a label can do it for me’ or, ‘If I just had a label deal then I could really do it!’ And I appreciate you really pulling back the curtain and saying yes, it can be a wonderful tool and it’s great that you have this team, but to demystify what it is and isn’t for our listeners I think we all really appreciate you taking the time to do that.


One of the things that stood out to me, and it stands out to me just from speaking to you as you’ve told your story – your ability to bring out the positive and see the beauty in what life has to offer and what who you’re choosing to work with, what they have to offer – it seems to me like everybody you’ve surrounded yourself with you all come from a genuine, authentic place. As you said with getting Josh to manage you, it was his belief and passion in what you could do that made you decide this is who I need to work with.

I got the same sense when I read about your experience in rehab. Coming out of rehab you wrote “The Good Life” and how it’s described as a sunny track after being in rehab which most people could get down on themselves about. And obviously I’m sure it had its hardships – would you be comfortable explaining to us a bit the role addiction has played in your life and how coming out of rehab has influenced your outlook and how you create your music?


Judah: I’m extremely comfortable talking about my addiction problems because that’s part of my recovery and therapy. First of all, I was addicted to Adderall from a very young age and it became something extremely regular in my life. The reason it turned into an addiction is because the feeling it gave me was this constant feeling of being almost on top of the world and high. It was an unrealistic way to live life – anything that was not surging with excitement was drowning in depression.


And it got to a point where my wife and manager and friends were like something’s really wrong. I was acting psychotic. I didn’t even notice it until I watched videos of myself before I went. The most eye opening thing was that I’m sitting in a room with people that are on parole for drug dealing, and I’m not going to allow my brain to convince me I don’t belong here for like the last time.


And it took some time, a week or two, for me to really embrace the fact that these other addicts are my family too. The realness of being extracted from your day to day life by a crane essentially, and plopped into this middle-of-nowhere place with strangers that are giving you a schedule for a period of 30 days is extremely frightening. It’s extremely intimidating. It’s uncomfortable. It’s the worst feeling I’ve ever felt in my entire life beyond funerals, beyond break ups – it was a horrible feeling to be in, but as I began accepting that I belonged there so that I can actually get out and live a clean life, I started allowing myself to embrace that feeling.

The way I related is I’ve had panic attacks for a while now, and sometimes in a panic attack it’s like a rollercoaster where when you’re going up the roller coaster in your mind you’re like, ‘Okay. I’m about to freak out. I’m about to freak out’ and then you could either catch it before the drop or you don’t.


For me, it’s like I’m on the drop already and I’m sort of able to, at that moment, say I’m not able to escape this rollercoaster right now. I’m on it, so instead of freaking out about something that I can’t control right at this moment because when you’re in a severe panic attack you just need to let it pass honestly. So I went and when I was done, I never felt more accomplished.

It was a very, very, very good threshold intolerance builder for unpleasant things in my life. I virtually don’t get bothered much anymore because of that, and I think my music has benefited from it because not only do I have more material to write about when I need to vent about something, it also made me realize how fortunate I am to be able to come back to the people that I left before.


Suz: That’s beautiful, and I’m so grateful that you shared that with us, as I myself have grown up in a family riddled with addiction, and I myself have battled my own demons and gone to therapy. And I related to a lot of what you said.


I love the outlook because everything is a choice and you have the choice afterwards to either look at it as, ‘Okay I did that but life ism I’m not as heightened or things aren’t as exciting as they were when I was on those things’ or you have a choice to, as you said, look at all the positives that breaking that addiction or dealing with that addiction allow into your life.

And the way you’ve chosen to look at it and the choices you made, from that point on are really inspiring and I also appreciate what you said about what it’s done for your music. I’m also curious, what role did music play in in terms of allowing you to get through this?


Judah: I wrote in rehab. I wrote a song called ‘Move On’ it’s on my upcoming album which is called Feelings In My Head. I did what I always do which is just write my feelings. It put me in a situation where I was very emotional and needed to vent.


When a song is out there it can emit many different types of emotions, and it could connect with people in many different ways. My rehab allowed me to just experience even more intense emotions in that moment. And it allowed me to write, I think, some of my better songs possibly because I had never felt emotions like that before and fear.


Suz: And one of the things that I noticed on your social media, a lot of your videos there’s such a great aesthetic to them, they’re very creative and they’ve just got a great sense of energy about them that clearly that’s something that you bring. You can’t teach that, and you really can’t force that. You can’t create it in editing.

The energy that you, yourself just being in front of the camera, bring to the videos it’s palpable. So I’m curious, when you create these videos, what is your inspiration for it? Do you talk with your team and plan everything out together? Do certain video concepts just come to you? What’s been your process with building your YouTube arsenal? Because it’s clearly connecting with your audience.


Judah: I try and stay out of the creative aspect of my videos because I’m a songwriter, and I am not a cinematographer. I’m more of a storyteller, so what I like to do is I think one of my best qualities is to know when to sort of shut up. Well my wife and parents may not agree with that, but in terms of working on my music…


I really trust the people I work with, and I like to give other people an opportunity to express their creativity through my music too. I don’t need to do everything. I can’t do everything. It’s so hard to write a complete song that passes my bar for good that I just don’t want to do all those things. So I’ve got a small group of people that I trust, and they generally will come up with a concept, then pass it by me. I’ll tweak it and we’ll move on from there.


But it’s really important, even for people who don’t have a team, what I mean by team – you really don’t need a lot of people, you just need people that you trust. And if you can find someone that you trust, I think that that’s much better than anybody with experience because together you’ll be able to figure it out.


Suz: Definitely. And one of the things you had mentioned before, how do you manage, now being out of rehab and now taking on so much with your team and your growing music career, do you have a structure now that you follow in terms of where you put your focus, what your role is for your career, and what you spend your time doing? Have you found, for yourself, your own structure that you can commit to?


Judah: I work closely with Josh every day on my own personal self. He does a lot for me aside from just being my music manager. I still have that same sort of like affected and tainted and almost like bruised brain that has gone through so much that sometimes you need an outsider who’s not in your immediate family to kind of jump in and give a non-biased, non-emotional opinion.

Part of my structure is really talking to Josh every day and between me and him figuring out whether I’m writing in the morning or if I have interviews or if I need to record an acoustic set or video – I rely on him a lot. Not to say that it couldn’t do it on my own, but while I have people there, I always plan to collaborate and hopefully through that experience gain my own comfort and be able to handle things on my own, but that might take time.


Suz: I love that. So many people want to team but then when they get it, it’s difficult for many people to delegate or give up control or rely on their team members, and I love how you’ve embraced that and know where their strengths are and how they can help you and how you help each other.


It also brings me to a segment in our podcast I ask all my guess these 4 rapid-fire questions. One of the things I think has been common throughout our talk today are all the lessons that you’ve learned and that you’ve acquired over the course of your life, and so one of our first question in our rapid-fire is, if you could go back and tell yourself a lesson to maybe save yourself some time, what would it be?


Judah: It’s going to come a lot later than you expect, and it’s gonna require a lot more work than you’d expect, and it’s not gonna be easy. It may take longer than expected but eventually, hopefully for everyone, but for me it worked out.

Suz: Absolutely. Next one is 3 musicians, living or dead, inviting them to dinner – who would it be?


Judah: Gavin DeGraw, Matt Kearney, and James Taylor.


Suz: Eclectic! I like it. If you could have one superpower what would it be?


Judah: End poverty.


Suz: Nice. So it brings us to our last question, it can literally be anything, what action would you like our listeners to go take this week?


Judah: I would like your listeners to find an individual that they trust and tell them that they trust them, and that they want to share with them some things involving their music or whatever it is so they could get some truly honest feedback from people that the trust.


Suz: I love that so much. And listeners I hope you’re paying attention! You’ve got homework to do. I’m gonna be putting that in the show notes, so you don’t forget. And my actionable that I would like everyone to go do is to go follow, subscribe, support Judah and his amazing music.

Judah, I want to thank you so much for taking the time, not only to speak with us, but to also to have been so open with us and sharing your your life lessons with all of us. I know our listeners definitely gained a lot, and I encourage everybody to connect with you because you’ve got a great spirit, an amazing talent, and I’m glad that there’s more people like you putting music out there, so thanks again!


Judah: Thank you so much for having me. I’m glad to give any advice I can. Thank you so much.


I want to again thank Judah for sharing his story with us. Don’t forget to go stream and download his latest EP, Young Hearts, you will not be disappointed. Head on over to www.therockstaradvocate.com/ep85 for all the links and be sure to connect with Judah on IG @judah_holiday.


I know there was a lot to unpack in our conversation, so here are the lessons I hope you’ve
taken away:

  1. Whether you’re battling addiction or simply struggling with opportunities not working out as
    you build your career, it’s important to practice the art of letting go – we can’t control what
    happens to us. We can, however control how we react and what we do with it.
  2. It’s important to find people in your circle you can trust. It may not always seem easy, but it is less scary when you remember that when you come across people you don’t gel with, you don’t need to continue the relationship. When collaborations go south or simply don’t take off, walk away respectfully and continue looking.
  3. Finally, authenticity is always going to resonate with your audience. It’s not about the millions of YouTube views or the record deals. Focus on connecting with your audience through your art and the rest will come.

As Judah said, structure is important in order to remember these lessons and sometimes you need an outside eye to guide you and reinforce that structure. If you’re looking for additional support in order to maintain structure in your career and daily life join us in Rock/Star Slackers™ my weekly accountability program.

With private accountability checkins throughout the week, weekly planning calls, monthly consulting calls and more you can have that team in your back pocket for less than $1.50/day. You can find more information in the show notes.

In my next episode I’ll be giving a behind the scenes look at what it’s like having a coach and when it’s a good time to get one. So be sure to stay tuned and reach out at any time if you have any questions or would like to chat! suz@therockstaradvocate.com.

Thank you for listening and remember, there’s always someone out there ready to listen to you.

If you’re struggling with addition or mental health stresses don’t wait to reach out. Talk to someone you trust or call one of the hotlines I’ve listed in the show notes today www.therockstaradvocate.com/ep85.

Until next time, Rock/Star! Have a safe and wonderful week and I hope to see you back here next time so we can get grounded to get rising! Take care.

Key Highlights

  • How music has been Judah’s lifeline throughout difficult points in his life
  • His process for finding his flow and linking with new collaborators
  • The reality of being signed to a label and what it means
  • The importance of working with people who you trust
  • How his battle with addiction and how it has transformed his life and approach to his music career
  • The one lesson he’d go back and tell his younger self
  • The 3 musicians he’d invite over for dinner
  • The secret super power he’d want most
  • His actionable for YOU this week:
    • Get real honest feedback from people you trust

Links/Rocksources

  • Theme music brought to you by DC-based Indie/Pop band Sub-Radio
  • More podcast episodes can be found here
  • You can download a copy of the episode’s transcript here
  • Check out Judah’s website here
  • Listen to Judah Holiday’s lates EP Young Hearts & singles on Spotify
  • Connect with Judah on Instagram, Facebook, Twitter, and YouTube

    Struggling with addiction? SAMHSA’s {Substance Abuse & Mental Health Services Administration} National Helpline is a free, confidential, 24/7, 365-day-a-year treatment referral and information service (in English and Spanish) for individuals and families facing mental and/or substance use disorders: 1-800-662-HELP (4357)

Start Slacking Your Way to Success!

CLICK HERE to learn how to gain a team of support for less than $1.50/day!

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