Headliner Mindset

SAN HOLO - The Delicate Dance of Art & Business

• Nik Cherwink

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What happens when your passion becomes your paycheck?

In this episode, San Holo and I unpack the real journey of turning your art into a business — and how to stay grounded when success starts pulling you in every direction. From his first viral remix on SoundCloud to headlining global festivals, San shares the mindset that’s kept him authentic through it all.

We talk about the creative struggle, the pressure to keep up with trends, and why staying different is both a blessing and a curse.

🔥 Topics we cover:
– The art vs. the algorithm
– Turning writer’s block into creative fuel
– Making peace with the business side of music
– How to protect your relationship with your art

This episode will remind you why you started — and why you’ll never be able to stop.

San:

we put a lot of weight on ourselves trying to up every day thinking create something beautiful day. and I realized, whoa, that's literally what I've been doing for the last 10 years. I wake up thinking I gotta make something of nothing. Pretty intense,

Nik Cherwink:

What's up everybody? Welcome to the Headliner Mindset Podcast. This week's episode is one of my most favorite conversations that I've had in a while where we really go deep in exploring that interesting dance between being an artist and being a business owner, creating from your. Authentic self-expression while also still existing in the industry and in the business, and what can oftentimes really feel like a push and pull. So get ready for a really beautiful deep dive into that dance. This is SA Hollow. San welcome to the show, brother. So happy to have you here. Thank you for making the time.

San:

Thank you for having me. I'm excited to talk.

Nik Cherwink:

Yeah, man. Um, you know, we were just talk,

San:

talk about.

Nik Cherwink:

I have no idea either. So let's see where this thing goes. I, I'm an open book, just like you said. You are a, a moment ago. Uh, I would really love to just start with. The beginning of your story and and hear a little bit about your background, like how did you get into music in the first place? When did you start your musical journey?

San:

Yeah. Um, really early. I was, I think I was 12 years old, uh, picked up a guitar for the first time when I was, yeah, about, about 12 years old. And, uh, ever since that moment I was just like, obsessed with, with music and, uh, I always thought I would be a guitar player or. You know, playing in a band or something. Uh, but

Nik Cherwink:

Yeah.

San:

the electronic music thing happened and, uh,

Nik Cherwink:

Yeah.

San:

making beats and that kind of blew up. And now I'm selling holo.

Nik Cherwink:

So, so how did it blow up? Right? I think that's everybody's question. Everyone wants to blow up. Uh, how did it blow up? I know that's a loaded question, but I'd love to unpack that with you. Like when was the first moment that you started seeing things really take off for you?

San:

2014 SoundCloud era. It was a, the SoundCloud was this exciting platform where people went to, to find new sound. It was, I think, not only new sounds but also new genres. People there were like putting music out that was kind of pushing all the boundaries.

Nik Cherwink:

Yeah.

San:

and, I was really inspired by that. I was on there every day just like listening to new music, like stuff I've never heard before wanted to be part of that movement, you know? So I started making my own stuff. Um, trap music was really big at that time, like heavy trap trap beats. Um, and I started doing like some chords and kind of cute melodies over the, over it kind of as a joke, not, not a joke. It was, it was serious to me, but it was, uh, kind of like a little wink to the, to the heavier trap music. I want

Nik Cherwink:

Yeah.

San:

throw some sparkles in there, you know.

Nik Cherwink:

Yeah.

San:

I've always been like inspired by, by, uh, doing things a little bit different,

Nik Cherwink:

Yeah.

San:

than what's expected. that I think, kind of resonated with people. And I, I did some remixes. I, I did, uh, the next episode remix for, Dr. Well, I said for Dr. Dre, but I honestly, I just ripped his vocals from, from, uh, a Google link. I just googled Dr. Dre next episode acapella. And I found this really low quality acapella, and I built a whole. Different universe around that acapella. And then Trap Nation, YouTube channel uploaded it and it blew up. And then I started getting calls like,

Nik Cherwink:

Yeah.

San:

you wanna DJ this party? I was like, dj, I don't, I don't even know how to dj.

Nik Cherwink:

Yeah,

San:

is. Yeah.

Nik Cherwink:

yeah. I, I, I love this because. When you did that remix, were you trying to blow up? Was that the intention was I'm, I'm right. Yeah.

San:

no. I was not trying to blow up. I was, I, I did know from, from a very young age that I wanted to really express myself through music

Nik Cherwink:

Yeah.

San:

that, that was, know, I, that was the thing that gave me purpose music and, yeah. I music, just something that I'm starting to realize now later in life that music has always been something to, to hold onto,

Nik Cherwink:

Mm

San:

creatively, also spiritually, expressing myself in a song. Sometimes I, I have to finish a song before I can feel that peace, you know? And

Nik Cherwink:

mm.

San:

it's, it's not always fun, it's, it does give me something to hold onto.

Nik Cherwink:

Hmm.

San:

And, um, so, so making those remixes or just like doing something creative, doing something different was, uh, in a way something that I felt called to do. It was just not, not like, oh, I wanna blow up, but it

Nik Cherwink:

Yeah.

San:

like I have to do this.

Nik Cherwink:

Do. Yeah, it sounds like it was more for you, like an internal process, like you even said even a spiritual process than it was like an ex, an external process, which I think so many people that are listening to this podcast are like, I wanna blow up. What's the strategy? How do I do it? You know? And now, you know, having a remix strategy as part of your game plan is like, okay, let me remix this artist so that I can get some attention. And DJs are gonna play it like, it's so in, it's so intentional and strategic, but it's coming from such a different place than what you're talking about.

San:

thought, I never thought about a release strategy back then. But you also have to understand if you, if you go back 10 years, look at Instagram. I think Instagram didn't even support videos yet. It was

Nik Cherwink:

Yeah. Yeah. Different era.

San:

Like social media was not about promoting your music or marketing. It

Nik Cherwink:

Mm-hmm.

San:

you know, Instagram used to be this hipster app where you would take a photo and you would put a filter on on there and everyone's like,

Nik Cherwink:

Yeah.

San:

looks like an analog, photo.

Nik Cherwink:

Yeah.

San:

so, so the whole landscape was so different. And, um, SoundCloud for, for me was, was that that exciting platform where people could leave a comment on the audio file, which was so exciting too, because you knew you made something like, let's say you made this crazy drop that you heard in your head, and then you put it out on the internet and then you would see people's reaction to that drop written down on the way file. So that was such a.

Nik Cherwink:

Hmm.

San:

beautiful experience.

Nik Cherwink:

Yeah.

San:

bring that back. Like we, we need, why, why didn't Spotify support that? That would be so cool to see people on tracks. Yeah.

Nik Cherwink:

Yeah. Like on the actual part of the song that got them, you know, most inspired. Right. But I think we're bringing up a really good. Dialogue here because yes, the landscape has changed, right? The marketing tools has have changed. It was a different era. SoundCloud had a different culture around it. But at the same time, I think the essence of making music for yourself and for expression versus making music to try to become famous and make it a career.

San:

Yeah,

Nik Cherwink:

ultimately two different things. And, not to say it's black or white. I'm sure you also still have some strategy in what you do. You know, now it's like, it's not one or the other, but I, I just think it's such an important thing to look at. And, and, and also I think this is what separates being a producer slash DJ versus being an artist. I think an artist is going to pursue making music because it's a calling. They have to, there's something inside of them that is genuinely curious and, and wanting to come out of your soul, versus when you're a producer, it's like, okay, here's, here's the formula, right? Here's what's happening. Here's the, you know, the trends and the labels, and there's a math and a science behind it. And again, not to say one is right or wrong, but I guess what I'm getting at is I want to really. Acknowledge you and celebrate you because from the first time I ever heard your music, I was like, whoa, this is some shit I've never heard before. This guy's doing his own thing. He's got his own sound, his own vibe, his own flavor. You weren't following any sort of trends per se, and, and you're someone that I really would consider, walking the true artist path in a very like, authentic way.

San:

This is, I really appreciate that. Thank you. First of all. Thanks for the compliment. It's very layered though. It's, it's

Nik Cherwink:

Yeah.

San:

And I, and you're touching on a very interesting uh, I think layered concept where. Um, you know, I've always tried to stick to my sound. Um, I see artists, the big pop stars, you know, you see how they go from genre to genre. You know, they, for example, they used to do big room, then they go future base, and then they go house, and now they do UKG, you know,

Nik Cherwink:

Yeah.

San:

I'm not hating on that. I'm just saying that's a different strategy. I personally wouldn't be able to do that because I've always been excited by things that stick out or are different from the common, um, yeah, what, what's popular and that, that sounds very hipster, but it's, it's not, it's, it's, uh, it's, know, is very interesting and, and. I've been playing with this thing for a long time. Um, I, music is intimate. To me. It's an intimate experience.

Nik Cherwink:

Yeah.

San:

And, and if, if you suddenly, if I would suddenly start making the stuff that everyone is listening to or everyone wants to hear, that doesn't feel intimate to me anymore. I love li listening to artists that are. You know, are doing their own thing, and maybe they're not famous or, most of my, most of the, the, the, my favorite artists that I listen to, they don't make a living off of music. They, they have a small setup in their room and they work at a coffee shop, or they have a day job, but they make gorgeous music, you know, and it just doesn't feed the algorithm. But, but that experience of listening to them very intimate. And something happens, you know, when someone blows up and everyone listens to them and l let's for example, Fred again. Like when I first discovered Fred again, I was obsessed with, with his, his sound and his sampling and his approach, and it was just I'd never heard before. And still, like he has carved out, oh, his own genre like that, his genre is kind of fret again, and people have kind of. Jumped on that train.

Nik Cherwink:

Yeah.

San:

there's something that happened when someone blows up big, where think the music is still insane and it's, he's an incredible producer and it's just good. can't deny it's really good. But the intimacy of when I first heard that song, I think it was called, uh uh, it's called I Found You. my God, that that song, I, and I, and I don't think anyone was really listening to it back then, but that intimacy with that song that you just discovered for yourself and No, and it was, no one knew about it. something that I really like about music and it's, it's,

Nik Cherwink:

Yeah.

San:

I wish, I wish I wasn't like that. I

Nik Cherwink:

Hmm.

San:

like that.

Nik Cherwink:

Well, and that's kind of the old traditional role, I would say, of a DJ in a, in, in, in certain areas was like to introduce new undiscovered music. And I guess, you know, it, it still is, right? Um, but yeah, it's an interesting thing to look at of the. The newness when something is still just surfacing and just bubbling and, and that,

San:

Yeah.

Nik Cherwink:

that intimacy of like, Ooh, I'm, I'm kind of the first person experiencing this. It hasn't been played out millions of times yet, and it has a different Yeah, nuance to it.

San:

to clarify, this is, this is not a, um, this is not saying, Hey, don't like him anymore because he went may mainstream, or That artist is bad because they sold out and they went mainstream. Not at all. This

Nik Cherwink:

Yeah.

San:

I'm just expressing my personal opinion, how I experience music, my relationship to music. It's interesting. It's, it's, uh, it's very intimate I

Nik Cherwink:

Hmm.

San:

um, and, and that's okay. probably just how I'm gonna go through life. I'm gonna hear something, uh, sometimes I hear a video on Instagram reels. I'm scrolling and I hear something. I'm like, whoa, this is, this sounds very special. And I

Nik Cherwink:

Yeah.

San:

it and I listen to it, um, because it sounds so, yeah. Beautiful to

Nik Cherwink:

Yeah. Yeah, I, how do you, I'm curious, how do you as a creator, as a producer, as an artist, continue to create. Outside of the box. Right. How do you continue to kind of stay fresh with your sound and not fall into, you know, repetition and continue to evolve?

San:

Yeah, for, for me, that's the only thing that, that drives me, you know?

Nik Cherwink:

Mm-hmm.

San:

Uh, I, I did an album last year called Existential Dance Music, and then, I played this dubstep festival, lost Lands, and that's more like a, you know, it's like a music,

Nik Cherwink:

Yeah.

San:

uh, lots of dubstep, brim, and I just thought, let's do something different. And I, I thought of this concept called wholesome rhythm, which is kind of like There's already melodic rhythm exists, but I wanted to bring a, a new twist to it. And I thought people were gonna hate on it, but people really liked the wholesome rhythm thing. Um, so I dedicated this year and next year to kind of doing that, exploring a new kind of, production method and, and style, wholesome rhythm era.

Nik Cherwink:

Yeah.

San:

really, really fun because I'm learning all these new techniques and, uh, it still feels like me, but then with a, with a different. Edge, a

Nik Cherwink:

Yeah. Yeah.

San:

It's not a choice to, uh, stay different. It is, a, a natural thing that I, if I'm making something that sounds like, like right now, if I'm making something that sounds like UKG or like, not hating on UKG, by the way, not hating on it, but. If I,

Nik Cherwink:

That's nice.

San:

in the studio and I make something and it sounds too much like what's popping right now,

Nik Cherwink:

Yeah.

San:

I naturally do change everything up so that it doesn't sound like that. And that's a blessing and a curse.'cause I wish I could just go along with the wave sometimes because it would be great for my career. That's, that's be honest, you know? But.

Nik Cherwink:

Uh, no, I love that though. I love that. You know, I've, I've seen this a lot with. Producers and, and also kind of more traditional record producers as well, when you sort of read some of their stories of how they made certain albums. And again, not to make it so black and white, but I, I do think there are, um, you know, different, at least two different approaches I see for a lot of. Younger kind of bedroom producers, they're just trying to find their sound or trying to find, you know, the formula, right? And it's like, okay, cool. Now I found this thing and now I can make a bunch of music. And, and, and really, um, it's almost like they've arrived at that destination as opposed to A lot of producers are kinda like, once I've done things a certain way, now I want to. I'm kind of bored of that. Like, what's next? Like what's the next kind of fun, interesting, different, exciting thing to chase. And I love reading these stories of, you know, record producers where they're like, okay, we, we did the last album this way. And now. Now, okay, it's time for a different album. And you know, let's see what it's like to. Hang the guitar amp upside down from the ceiling fan and see what that sounds like. And let's like, you know, let's try this out. I've never tried this before. Here's a crazy idea. And, and it's more of chasing and following the curiosity of like, what's possible and what's next, rather than what's been done and how do I figure out how to do that?

San:

Yeah, exactly. And, and I think, um, everyone, everyone's relationship to music is different. That's something that I have learned throughout the years and I navigate my music journey through my relationship with music. Um, but music for someone could. I just wanna have a good time. I want it to make me happy. You know, I've,

Nik Cherwink:

Yeah.

San:

I've, I've talked with several people who, who said, um, oh, I just wanna play music in the car. That kind of makes me feel like uplifted and happy. I don't want music to make me sad. I, you know, and for me, it's the opposite. I, I want to play music that digs

Nik Cherwink:

Mm.

San:

soul, you know?

Nik Cherwink:

Yeah,

San:

so, so it's different for everyone,

Nik Cherwink:

totally.

San:

no right or wrong. Um, that, that, that was a very, really, uh, fascinating realization that, that, wow, like music is not just this, the function of music is different for everyone.

Nik Cherwink:

Mm-hmm.

San:

mean?

Nik Cherwink:

Yeah. Yeah,

San:

of it.

Nik Cherwink:

yeah.

San:

yeah, it's interesting

Nik Cherwink:

And none of it is right or wrong. Right. I think that that's really important too, is like, yeah.

San:

I'm grateful for,'cause my, you know, I'm, relationship to music emotionally is really complex. I love it. But I also, sometimes it kills me when I'm writing a song. You know

Nik Cherwink:

Mm.

San:

I, but when I can't get it right, it's not fun. A

Nik Cherwink:

Mm

San:

It's not a hobby in that sense. It's not

Nik Cherwink:

mm.

San:

I'm gonna go play tennis. And have some fun, you know, like it's, uh, um, I guess if you, if you take it that seriously, everything becomes not only fun, it becomes more of a calling,

Nik Cherwink:

Yeah.

San:

like a thing, thing to figure out. And uh,

Nik Cherwink:

Yeah,

San:

you know, right now I'm working on this song and I'm just like, can't get it right. And I feel this unease in my being, you

Nik Cherwink:

yeah, yeah. And, and how?

San:

me, it's that serious.

Nik Cherwink:

And how do you work through that when you hit those creative blocks, not being able to really find the, you know, resolution to the song that you're, that you're seeking. What do you do to work around that?

San:

I, I think I, I don't know. It's not a, it's not a working around, it's about just, maybe it's not the, maybe that's not a problem. Maybe that's

Nik Cherwink:

Hmm.

San:

my strength. I take it that personal and that hope, you know, I hope that people hear that. I hope that every sound I pick, you know, you can pick any sound of, of and I could tell you where it comes from and where I was at that time and how I was feeling.

Nik Cherwink:

Yeah.

San:

for some other people making a song by me. Just more like, let's make a banger. Let's make something that feels good. You know, like,

Nik Cherwink:

Yeah. Yeah.

San:

also good and that's beautiful in its own way too.

Nik Cherwink:

Yeah. Well, I think you just said something so profound, which is that what if struggling with your song or having a creative block isn't a problem? Because we look at that as being a problem, right? It's like, oh, I want to come in and just be inspired and, and have flow and all of that. But there's almost this, this wrestle that you get to have with your music is the whole point, right? It's, it's kind of like, it's like life. It's like, oh, what if I just always wanted to be happy and everything always worked out all the time in life was just that. It's like, no, that's, life is also pain and struggle and challenge, but that's what makes you who you are. It's what makes it fucking beautiful.

San:

Yeah. That's why I, I always tend to, you know, I get, I get artists asking me like, Hey, what do you do when you've got writer's block? and, uh, you know. We like to create diagnosis like as people, right? We like to diagnose ourselves like, oh, I, I

Nik Cherwink:

Yeah.

San:

I can't work right now'cause I have writer's block. I, does it really exist? Like, isn't it, isn't it just like life happening?

Nik Cherwink:

Yeah.

San:

you don't want to claim that term. You know,

Nik Cherwink:

Mm.

San:

don't wanna, if

Nik Cherwink:

Yeah.

San:

you're, maybe you're already writing when you think you're not writing. Sometimes I'm, sometimes I, oh, the other day I had this. I was trying to just create something'cause I couldn't create like a dance strike that I was working on. So I played some guitar recorded some guitar noodles and I thought, oh, this also sucks. So I created this guitar loop and I was like, it's whatever. And then I reversed it and chopped it up, and then something happened. And uh, now I'm working on that song. I put a beat on it and like it's my favorite song. So I was already writing that song, Like subconsciously there was already, struggle was already doing something to me

Nik Cherwink:

Yeah.

San:

next song,

Nik Cherwink:

Yeah.

San:

know.

Nik Cherwink:

Ooh. And just to expand that perspective even a bit more, we can potentially limit ourselves to thinking that writing the song only exists when I'm sitting down at the DAW or the guitar and I'm, you know, quote unquote working on the song. But what if also it's when I. Go to the beach that weekend and I jump in the water and I feel the sand on my toes and I experience life and I have a conversation with a friend that that's also a

San:

Yeah.

Nik Cherwink:

my mindset, my personality, my emotions. And then when I go back to sit down again, all of that is being brought into the song. So when are we ever not an artist?

San:

Yeah. That, and that's the thing. And that's also the, the weight, right? Uh, I had a conversation with, with someone the other day and he said, uh, you know, we put a lot of weight on ourselves trying to up every day thinking create something beautiful day. That's, and I realized, whoa, that's literally what I've been doing for the last 10 years. I wake up thinking I gotta make something of nothing. I gotta create something, gotta create beauty, gotta create. I'm not saying this to myself. I'm not looking into mirror and saying, you gotta create beauty. No, it's, but it's this feeling inside. You wanna create, create, create, um, pretty intense, you know.

Nik Cherwink:

Yeah. Yeah. And what's a different mindset and approach to have? Rather than I have to create something and then that feels heavy. Like what's another mindset to step into around it?

San:

You know, I'm still figuring that out. Maybe it's, uh, don't know. I, that I still feel it. I still feel, um, a little bit of an ease when I'm not, uh, creating.

Nik Cherwink:

Hmm.

San:

it's, I, I don't know if it's a bad thing or if I need a better relationship with it, but, um,

Nik Cherwink:

Hmm.

San:

it's also the artist's struggle, I guess.

Nik Cherwink:

Hmm.

San:

I dunno. It's uh, I just realize there's so many, everyone is so different. Everyone is so different. Every artist is different. Some artists just are very focused. They say nine to five, I lock in, and then whatever happens that day. I, I, start and I close it, and then I go back home, and then tomorrow we start again. I, for me, it's a, it's, never ending, also never starting. You know, it, it, it's, I could have a conversation with you today that inspires a whole record, you know? Uh,

Nik Cherwink:

I hope it does. San Holo Headliner Mindset EP coming out 2026.

San:

Yes.

Nik Cherwink:

Hmm. I love that. Um,

San:

Collab, collab of the century.

Nik Cherwink:

yeah.

San:

I did wanna say something. We, we kind of, we kind of, uh, you know, kept on talking and it was, uh, I, I enjoyed the free flow of the conversation, but you did say something earlier that I wanted to talk about. Um, the. I, I wanna put the record straight. I, um, you said back, back in the day like that I made music out of, um, just a pure passion perspective, right? Like, not just with the idea of like, I wanna blow up, I want to be famous. That is correct. Um, but I can't deny that right now, 10 years down the line. I do definitely feel like part artists, but also running a business, you know,

Nik Cherwink:

Yeah,

San:

also, I am, um, is a choice and it's a choice I've made and sometimes it's a struggle with the, the creative part inside of me

Nik Cherwink:

Hmm.

San:

and navigating that has been really interesting throughout the years.

Nik Cherwink:

Yeah. Why do you say it's a choice?

San:

Because, uh, you can be an amazing artist. You can be an incredible artist and not get paid anything for your work.

Nik Cherwink:

Yeah.

San:

You know, that's just a fact. I know a

Nik Cherwink:

Yeah.

San:

artists that are not getting, paid or living off of their work

Nik Cherwink:

Yeah.

San:

and I think if you want to live off of your work, that's that some. There has to be some sort of businessman in you

Nik Cherwink:

Yeah.

San:

or, you know, and that's the struggle. And I, and I'm not, I'm, that's not my natural state, not my

Nik Cherwink:

Yeah.

San:

state to think about budgets and how to market it. And, but it's a choice I've made and for now I've decided to, to. Play that role sometimes

Nik Cherwink:

Mm-hmm.

San:

and, and, um, but it's not, not going to be forever. It's

Nik Cherwink:

Yeah.

San:

I

Nik Cherwink:

Yeah. Yeah.

San:

want to do that.

Nik Cherwink:

Yeah, this, this is something I talk a lot about on the podcast is, you know, for every artist that's out there that's making music, and you know, by all means, make music and love the process. And, and, and if at some point you want to be successful in the music business. You also get to start a business, right? In order to have it turn into income, in order to market yourself, build a brand, play shows, make money, all of that. Like you have to become a, in the beginning, a self-employed entrepreneur, you are a business owner, and that's the big struggle for a lot of people is I love making music. I don't necessarily love being a business owner, and one, you don't have to, but. But two, if, if you want to, you know, turn it into a career, I think it's an inevitable, an inevitable part of the process.

San:

Even hearing you talk about it, like being like, you have to be an entrepreneur and stuff, and like that, it's, it is a harsh reality.

Nik Cherwink:

Yeah.

San:

but it's not a nice, it's that the, the art that comes from the heart and the love that you pour into it is so detached from, from those concepts, those numbers, and.

Nik Cherwink:

Yeah.

San:

It, it is an intimate world that you feel inside yourself, that you feel like you wanna express and put out basically what you wanna put out. Love into the world.

Nik Cherwink:

Yeah.

San:

you wanna do as an artist. Whether it's with sad music or with happy music, or with whatever type of music you wanna put love into the world.

Nik Cherwink:

I'm so curious to hear your perspective on this because I've seen this and, and I've worked with a handful of artists. I do life coaching, four artists specifically, and mindset coaching where I've had artists where you, when you start. You're not thinking about the business. And so you're making music from a place of pure joy, fun, passion, creativity, and then that's what makes the music successful is because there's a certain kind of energy that you're putting into it. I think similar to you. You're like, I wasn't trying to make this remix blow up. I was just having fun. And then it blows up. It gets a lot of attention. Everybody falls in love with it, and now all of a sudden, whether you realize it or not. You're running a business, you're in the business, and now, now you're touring. This becomes the full-time job. All of a sudden, you have to keep touring to pay the bills. All of a sudden there's a whole different level of, stress and pressure and contracts and, you know, touring and, and so now you're also trying to be creative, but it's, you're not in the same place that you were before. So the, the trap I often times see people fall into is now I'm making music more as fuel. To keep the business going so I can kind of keep the bills paid. And then I'm now probably losing that passion. I'm losing that same spark. Right? And so a lot of the, a lot of the work that I've done with people is like, how do you get realigned with that spark again? Um, but it's, I think it's an inev and, and inevitable part of most artists journeys. And I'm curious if you've experienced that for yourself as well.

San:

That's, uh, a hundred percent what I experience.

Nik Cherwink:

Mm-hmm.

San:

touring makes, touring makes things a lot more complex in terms of you have a touring artist project, there's a lot of costs that come with that. And a lot of risk, a lot of people involved and it's an amazing experience getting to tour. It's it that itself inspired me so much. Being able to, to Asia next month to play Korea, Japan, and China. you lent in China. I lent at the airport and there's people the other side of the world with my merchant. presence. And it's not that that inspires me, that, oh, I'm famous, but like the, the fact that they have had an experience with my music on the other side of the world, they connected to something that I made in my bedroom that is inspiring to me. Not the being there and, and getting gifts. That's, that's of course. But the fact that people connected to it from the other side of the world is beautiful to me. However. The touring side is just, um, extremely stressful because there's a lot of money involved with getting your production to every, every venue. You know, you have, you have your crew that needs to get paid. At some point you start to think, oh. For example, right now I would love to work on an ambient album, right? I would love to

Nik Cherwink:

Yeah.

San:

guitar album. Let's say I just wanna play guitar and like noodle around and record that and get really creative. But at the same time, I also wanna tour next year

Nik Cherwink:

Yeah.

San:

and, I'm gonna show up at festivals and play an ambient guitar set as San Holo, people are

Nik Cherwink:

Yeah.

San:

You

Nik Cherwink:

Maybe, maybe not at Lost Lands.

San:

Yeah, maybe. Yeah. Or maybe

Nik Cherwink:

Yeah,

San:

the next time.

Nik Cherwink:

yeah, yeah, yeah. Well, what do you, what do you think is the solution and, and what have you done as a touring artist to, um, to stay. Grounded and balanced in the midst of all of the moving pieces and the pressure that comes with being a touring artist.

San:

I think for me, accepting that, that it is a choice for me right now to,

Nik Cherwink:

Mm-hmm.

San:

to do this.

Nik Cherwink:

Yeah.

San:

I know that I can always fall back to art the way I started. You

Nik Cherwink:

Yeah.

San:

I don't have a responsibility to, uh, I can, I have to, I can decide. This gives me peace. Some, some type, sometimes to. Stop tomorrow and say, Hey,

Nik Cherwink:

Yeah.

San:

fun. I'm gonna go back to me and a little guitar recording some stuff, and I don't care who listens to it. This is just for me.

Nik Cherwink:

It's so huge because back to what you were saying about waking up and feeling the pressure of I have to create something great today. I know for you that's coming a little bit more from a, almost like a spiritual perspective, but also also it can be the,

San:

business

Nik Cherwink:

now it's like, yeah, I gotta keep the business going, so I gotta create the next album or whatever. And when we are stuck in the mindset of I have to. Right.

San:

Yeah.

Nik Cherwink:

We make ourselves powerless, but shifting into, I'm choosing to, and also like I get to, this is a choice. I get to do this. It's a big perspective shift that really changes the entire game. Like, this is a choice. Nobody's holding a gun to my head and making me get outta bed and make music, or making me get outta bed and, and go on tour. Right. And, and to ultimately step into, you know, that, that. State of like, wow, like I, I get to do this every day. I'm blessed to do this every day. Right? And it can be easier, easier said than done to just think your way into that. But if every day we're waking up and we're like, fuck, I have to do this. Oh my gosh. It's like, okay. That's the first step to look to work on is like, how am I, how am I seeing all of this? Like it is a choice. So I love that you point that out.

San:

choice for me to me be clear. It's a choice for me to, to do this, to do music and also to do the music industry. That's a choice

Nik Cherwink:

Yeah.

San:

to do. Music is a calling

Nik Cherwink:

Yeah,

San:

the music industry. It's a choice.

Nik Cherwink:

yeah. I don't think it's a choice for you to do music. I think you have to do music for your, for your soul and for your spirit, right? Yeah,

San:

is a, music is a calling, and that's what I will

Nik Cherwink:

totally.

San:

till the day that I die.

Nik Cherwink:

Yeah.

San:

industry is a choice and I have, uh, with that choice, seeing it as a choice also enabled me to get inspired by navigating that. So getting inspired by touring the world. And getting inspired by, what do I want versus what does the world want?

Nik Cherwink:

Yeah.

San:

that whole process is you can find inspiration in that too. It's an art in itself. I, I spoke about it with my therapist the other day, and, uh, she said, you know, balancing those two things, um, instead of viewing it as a. An evil thing. You could also see that as an inspir inspiring thing. You know, it's an art in itself. How to,'cause here's the thing, I went to school for music. Uh, I started guitar. And everyone teaches you how to, how to play guitar, how to make music, how to, maybe even these days they teach you how to market it. I don't know. no one teaches you what to do when it. When it's happening, when, when it works, when it's,

Nik Cherwink:

Mm-hmm.

San:

it, when you're doing it. The, the whole, the, the psychology behind that. You can't teach anyone that. It's an experience that you, some point hopefully for everyone's watching. I hope that you get to experience that.

Nik Cherwink:

Yeah.

San:

but then you're kind of on your own, you know? And I guess that's why people come to you also and like say like, yo, what the hell? Like what am I,

Nik Cherwink:

Yeah.

San:

I do?

Nik Cherwink:

Yeah. Well, as somebody who has been doing it, obviously your journey is unique, and it's your life and your world, your universe that you've created. But what are some tips that you would give to artists that are about to take that step and, and get outta the bedroom and start touring? What are some, what if we had the course to teach and offer, what would some of the lessons be in that?

San:

Look man, like advice from me. Um, is that everyone is so vastly different. Every person is so vastly different. I, my advice would be don't listen too much to, to the advice everyone is throwing at you.

Nik Cherwink:

Yeah.

San:

that might work for them, but what you might need, you know, sometimes I see people talk and say, you know, here's. you should get into the studio and finish a song in 30 minutes and then do the, do the, like, create five ideas in a session. And, and I would, I would feel terrible doing that. I, I spend a month on a song, you know, sometimes like, and I go, go for a walk at night, listen to the lyrics and change the lyrics up because it doesn't feel right and, you know. You, you might say, oh, that's a terrible process because it's not effective. But if that's how you operate and that's how you get your motivation and, and inspiration, might to say that you should make five songs

Nik Cherwink:

Yeah.

San:

You know?

Nik Cherwink:

Yeah,

San:

a lot of that content. You see a lot

Nik Cherwink:

yeah,

San:

of, of people saying this, do this. Here's my advice for you. Do that. Like, and I, I think you can't just. Should advice, general advice to everyone. It,

Nik Cherwink:

Yeah.

San:

person should be treated as an, as their own universe. You're a whole universe. Your,

Nik Cherwink:

Yeah.

San:

your, the way, your, your culture, your religion, your parents, your relationship to art. so deep, and I think this. You can't really cut this into a nice Instagram reel. My answer, you know. I wish I could just say, here's my advice, do this, do

Nik Cherwink:

Yeah.

San:

But I think my advice is more, more, uh, um, fluid in terms of, advice to you would be, um, just because something works for someone else doesn't mean that it will work for you. There's no right way of doing it. only right way would be to follow what you feel works for you. There's not one hack that works for

Nik Cherwink:

yeah, yeah. Dude, it, I really. Beautiful answer because if you look at E everybody that is, you know, achieving the goals that you might want to have, let's say touring, you know, has built the business, and then you look at what's the path that they took to get there. There's 500 different paths and so you know your path. I think a lot of people are looking at, they're looking for. What's the answer, right? What's the formula? How do you do it? What are the, what's the recipe for success? And I just think you completely nailed it, and it's a great reminder for me as a coach, because that's how I was trained as a coach initially, was that we don't give answers. We just ask questions. You have all the answers inside of you. My job is just to hold space, probably like your therapist is just, they're just asking you questions. What, what's your truth? What's alive in you? What's real for you? How do we draw that out of people rather than, giving all the answers. So, really good reminder for me,'cause I've kind of lost touch with that a little bit. I have started creating some playbooks and formulas and, you know, this is what works. But like you said, it might work for you, it might not. Every, you know, there's no one right answer.

San:

that, that's, that's part of that, uh, what you're talking about. Like, you know, you've done your concessions, you wanted to grow. Your socials too. And then, you know, sometimes that's about playing the game a little bit, And that's sometimes me making a song that, and I feel like, oh, maybe we should, uh, maybe it's a good idea to make a dance record and not an ambient record right now, because I want to go on tour next year. You know, like,

Nik Cherwink:

Yeah.

San:

a, I think what we're talking about, if I can like add something to my advice, it would be to, if you're an artist and, and a musician. sure that your relationship with music is solid.

Nik Cherwink:

Hmm.

San:

the music industry thing, you know, you can get the advice and the tricks and the, and the what to do on TikTok and all that stuff. That's, but that's not really part of the music,

Nik Cherwink:

Yeah.

San:

music world,

Nik Cherwink:

Yeah.

San:

And I think if you stay. At least at you, you know, your relationship to music and what it means to you and what's important to you when it comes to true music and art, then you might be able to navigate, um, the music industry with a little bit more peace of mind.

Nik Cherwink:

Yeah.

San:

Um.

Nik Cherwink:

Yeah. Thousand percent because the music has to come first. It doesn't have to. I would prefer if it does, I think this is, if you wanna be the an artist versus just being a producer slash dj, if we wanna look at it from business terms, create the product first, and then go learn how to market it and sell it. But you gotta make the thing first and make that thing, you know, from a place of, uh, I don't wanna say isolation. But from a place of looking inward, rather than looking so much outward.'cause the other, the other way is looking at what's happening, what's happening in the industry, and then trying to create your, you know, product for lack of a better term. From there. Again, neither is right or wrong that. Can work and it does work. There is a formula. Also, AI can fucking do it for you now, so good luck with that, right? But, but I think the path that we're talking about really as an artist, right, make the, make the music first. Make the music from your own taste, your own self-expression. And then figure out where it fits in, then figure out, you know, how do you build a brand around it in the marketing. But if all of that's coming first, it's gonna, it's gonna affect the creative process and I think probably be a little bit less fun, you know.

San:

well, and that's the thing. Some people can do that. Some people can, uh, let's, let's be honest, some, I think there's. Artists out there that are more businessmen than than artists, and that's

Nik Cherwink:

Oh yeah.

San:

That's, that's, that's the whole, that's the painful part

Nik Cherwink:

Hmm.

San:

for, for a lot of artists, I think. I

Nik Cherwink:

Mm-hmm.

San:

part for a lot of artists is to see that people that are really good at, at marketing and, and building a, a company and building a brand sometimes also get to really. Be in the spotlight'cause of

Nik Cherwink:

Yeah. Yeah.

San:

I think what I'm really trying to say is, um, what I, I agree with everything you said about the music comes first, but you do have to, to ask yourself the question, do I want to be part of the music industry? You know, that's a good question. Do I want to pay the bills with music? Do I want to live off of my art? And if that's, so then there's things you could do that would help with that. You know,

Nik Cherwink:

It's such an interesting dance. It's such an interesting dance.'cause it does get, it does get to be both, as we said in the beginning, if you want to. Have a business, have a successful business in the music industry. You get to be a business owner. You also get to really understand how the business works and understand all the ins and outs of the business and understand branding and marketing and, and, and all of that. Um, so it's a really interesting balance of how to lead with authenticity and, um, yeah, authentic. Creativity while also. You know, being really good at the business. I, I, I think you said something a moment ago about, you know, there are these guys and, and yeah, let's be honest, let's be real. There are artists out there, huge, big headlining artists where their job is now to run a multimillion dollar touring business with 50 people on their team, and they're not spending eight hours a day making music anymore. You know, they have other people that are helping them with that, and it's this whole machine. Welcome to the music business. Not even 2025, but,

San:

just,

Nik Cherwink:

that's,

San:

real.

Nik Cherwink:

yeah,

San:

real. They don't make the music anymore.

Nik Cherwink:

yeah, yeah. And, and, and, because,

San:

but.

Nik Cherwink:

yeah, but it's true. And that,

San:

it's

Nik Cherwink:

and the thing is, KA Perry doesn't produce her music either. Pop artists aren't doing it, you know what I mean? And, and now EDM has become pop in that sense. And it's following a bit of this, this, you know. Reality of how the music business works in some of these other areas. So, you know, being an artist is more about, yeah, being the face, being the dj, and running the business. And what I would say is cool, like if that's what you want for your life. Awesome. Do it. You have been called. Yeah, yeah,

San:

to music is different,

Nik Cherwink:

yeah. And, and you've, you've been called to make music, express your feelings. Right? It's like you, as you said, you can't not do that. You, I love it, dude. I love it. And none of it's wrong. None of it's right or wrong. We all get to have our own place. I've found this weird. This weird little space in the music industry where I get to be a coach. Didn't plan on that, but following, you know, similarly following my own passion, my own creativity and inspiration. And at one point realizing like, well damn, if I wanna like actually have this be a business. I do get to do the marketing. I do get to like, you know, learn certain parts of the business, which maybe it's not as fun, but, you know, we're all, we're all figuring out our, our place in it. And, um, I think finding what, what feels true for you is important.

San:

so you, so you know, you made a decision to, okay, let's do the marketing, let's do this,

Nik Cherwink:

Yeah.

San:

but, but, but your true passion would be still there if the cameras were off. Right? If you're

Nik Cherwink:

Oh yeah. I would prefer them to be, yeah, I would, I I would love to just coach all day, give me five clients a day and, and let me fucking rip in and Oh yeah, I would love that. But in order for me to get those clients, I get to put myself out there and let people know that I exist. You know, similarly to you music, it's like you would love to just make music all day, but if you want to have people hear it and come to your shows, you gotta put it out there, right? Come, comes with the territory.

San:

concept of this. This explains my concept of, you know, you've got the. The music or the art or the passion.

Nik Cherwink:

Yeah.

San:

with passion.

Nik Cherwink:

Yeah,

San:

And then you've got the, the business side of things. And

Nik Cherwink:

totally.

San:

and that is a choice. If you want to make a living off of your passion, then

Nik Cherwink:

Yeah.

San:

you have to

Nik Cherwink:

Yeah.

San:

Uh, there's

Nik Cherwink:

You know something.

San:

of course cases where that writers, there's wild cards where some people just really only do whatever the fuck they want and they have a viral moment or,

Nik Cherwink:

Yeah, yeah,

San:

uh,

Nik Cherwink:

yeah, for sure. You know something, one of my coaches told me early on when I was just starting to kind of build my coaching business was he was like, look, if you,'cause for me, this is a calling too. I honestly, I would rather go get a tech job here in Austin. And make, you know, 300 grand a year selling fucking software and just like have a mindless, simple, easy job. I've been called to do this shit. I've tried to walk away multiple times and God, the universe has said, no motherfucker. Get back there and serve these people. And what this, what my coach told me early on was like, look, if this really is your calling, if you're actually really about the service that this is providing, and you feel in your heart and soul that this is what you're supposed to be doing, then. You'll be willing to do. The other hard stuff that comes along with it, right? Like, you'll be willing to go work the job at Starbucks while you're building your coaching business because you're actually fucking about it. Right? And I think similarly, as an artist, the same thing. The passion. Like, look, if you really love it, you'll be willing to, you know, do the business stuff that maybe sucks, but it's all there to support the dream, the vision, the passion, the creativity, right? So,

San:

is not,

Nik Cherwink:

yeah.

San:

is not a choice. You would say the

Nik Cherwink:

Yeah.

San:

not a choice.

Nik Cherwink:

Yeah.

San:

you doing, you want you wanting to do this. That's not a choice. That's

Nik Cherwink:

yeah, yeah.

San:

a, it's a very interesting thing to talk about the calling.'cause that's a, I feel like people don't really realize that if, if,

Nik Cherwink:

Hmm.

San:

if you just keep giving, getting back to it, coming back to it, if you wake up every time still thinking about it,

Nik Cherwink:

Yeah.

San:

there. And, and for me that was music.

Nik Cherwink:

Hmm.

San:

like I, I had a friend in high school and, uh, he, um, was very talented, probably more talented than, than, like, way better producing music and, and his instrument than I was, he, didn't feel called to

Nik Cherwink:

Mm-hmm.

San:

that for the rest of his life.

Nik Cherwink:

Yeah.

San:

and he's very happy right now.

Nik Cherwink:

Yeah.

San:

there was, there was, from the

Nik Cherwink:

I.

San:

picked up a guitar, was like, you know, was like, this is it.

Nik Cherwink:

Yeah.

San:

a guitar player too, right?

Nik Cherwink:

I am, I am. Well, yeah. I just, I just played my very first show. Uh, shout out Bella Renee. I am not sure if you're familiar with her. She's like a, a singer, kind of the drum and bass world. But yeah, she just, I, I just sit here in my, in the corner of my room and I just, you know, I don't really claim to be an artist. I just jam metal riffs just for fun. And she was like, yo. Come get on stage with me and play a couple songs. And so I just had my first taste of playing live and now I'm like, oh shit, I wanna get back out there. I got, now I got the bug. Now I'm like, okay, let's, let's do that again. That was fun. Yeah, yeah, yeah. Um, I wanna ask you this,'cause you know, I, I just shared, like, I've definitely, it's such an interesting dance of. Passion and business and all the, you know, the stress and pressure that comes with that balancing, you know, just trying to find that balance in that dance. Like I've definitely had a couple moments where I was just like, ah, fuck this. I'm over it. I'm ready to walk away. Have you ever reached that point where you were ready to just step out and be done?

San:

Yes, uh, it was right, right after the pandemic. Um, I was about to, uh, part ways with my management. I was on tour the first, I think the borders just opened up again, and everyone. The COVID just ended officially while everyone was still masked.

Nik Cherwink:

Hmm.

San:

was touring and the second day off tour, one of my main guys, uh, got COVID and everything. Just kind of the whole tour we were just about to do, just kind of got, I just got so close to like, oh, you know, let's just call it off because we're never gonna get through this three months of touring tests every day. mask, meet and greets every day to pay for the costs. You know,

Nik Cherwink:

You already put all that money up into the tour in advance.

San:

Like,

Nik Cherwink:

Yeah.

San:

and greets. Like, and, and even though I love, I love meeting the fans and I, the, the people that support and listen to my music, I don't like calling them fans. I, I always like to call them listeners or, or, um, they, I love, I love meeting them, but. A hundred people a day with masks on

Nik Cherwink:

Oh man. That's a lot.

San:

so, I was just kind of hoping that I would not get COVID every day. And you know, one of my most important crew members got COVID, got hit with COVID and I was just like, you know what? I don't, this is not giving me any fulfillment. It's just stress at this point. It's only stress. And uh, we pulled through, you know, at

Nik Cherwink:

Hmm.

San:

and. some point the, we had to, I had to carry the, the flight push to flight cases. You know, we had a show in San Diego and, uh, everything was so dis dislocated. I had to just like travel with two other guys carrying all the cases, like what, 10 cases. I was pushing the cases and I was like, that also gave me some kind of strength. I was like, you know what? Fucking go. And,

Nik Cherwink:

Yeah. What, what kept you going when you kind of reached that, you know, you get to that edge almost to that breaking point. Like what, what kept you going in those? That tough moment?

San:

I don't know. I think, I think that's that calling, that's what, what, what, that's how, you know, I think the, an, the question to ask yourself is like, would you be. Making songs or making music. If only five people were listening, you know, or only one person would be listening, would you still do it? And for me, the answer is yes. know, I, I love it. I love, it's, it's not, it's mostly an internal process for me. The music and the, the journey. Um, I would definitely work at Starbucks if I have to, you know. I, I would definitely work at Starbucks or a coffee shop, and on the side I would do music. I'm, I'm never gonna quit this. I love doing this, you know,

Nik Cherwink:

Damn well. That is an epic mic drop moment to end this episode on that, I, I, I really, I had a handful of bullet points and questions and things I was thinking about asking. I didn't look at one of them throughout this entire chat. Uh, I really, really love your mindset and your perspective and the passion that you have for this. And again, just really want to, yeah, man, just celebrate. You really pursuing the true hero's journey of being an artist. It's incredibly inspiring, and I thank you so much for taking the time to, to share some of your energy with us and, and, uh, not the fans, but the audience, the Headliner Mindset community. Shout out to all of you for listening. I love you guys and, um, San thank you so much for coming on today.

San:

Thank you very much for having me, and I just wanna say I'm not the hero, everyone working that coffee shop job with a thousand or like 500 monthly listeners. You guys are heroes to me. I, I'm listening to you like, that's the stuff I love. So keep grinding.

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Nik Cherwink

Host