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How To Win The Algorithm, Even If You Hate It - Dylan Gossett (Live Performance)

Dylan Gossett is a country singer, songwriter, and music producer. Dylan's breakout hit 'Coal' took him from an aspiring musician in Austin, Texas, to a rising name in country music. But what did that seemingly overnight success actually take, how has it changed his life, and what has he learned about making a living doing what he loves? Expect to learn the creative process behind Dylan’s hit ‘Coal’ and the decisions he made to engineer it for max virality, what it was like being an overnight success, how Dylan’s writing process differs from the typical Nashville music machine, the impacts of AI on songwriting and the music industry as a whole, how to not be captured by your audience and let your creativity thrive, and much more… - Get up to $350 off the Eight Sleep Pod 6 at ⁠https://eightsleep.com/modernwisdom⁠ Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom Get the brand new Whoop 5.0 and your first month for free at https://join.whoop.com/modernwisdom Get 10% discount on all Gymshark products at https://gym.sh/modernwisdom (use code MODERNWISDOM10) - 0:00 The Story Behind Dylan’s Breakout Song ‘Coal’ 9:56 How to Avoid Getting Lost in the Music Industry 18:11 Why Being Unpolished Feels More Authentic 20:50 Is Country Music Having a Renaissance? 22:47 Is the Song Actually Good or Just Viral? 28:07 Why Staying Successful Is Harder Than Getting There 32:29 Inside Dylan’s Songwriting Process 37:28 Do Artists Still Write Their Own Songs? 51:02 Why We Shouldn’t Always Take Shortcuts 01:01:16 Is Emotion the Secret to Dylan’s Music? 01:03:08 Why Sad Men Are Taking Over Country Music 01:09:24 The Hardest Emotions to Turn Into Music 01:14:52 Don’t Lose Yourself Chasing an Audience 01:22:59 A Snippet From Dylan’s New Album - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

Chris WilliamsonhostDylan Gossettguest
Sep 26, 20261h 29mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 9:56

    The Story Behind Dylan’s Breakout Song ‘Coal’

    1. CW

      People of the UK and Ireland, I'm coming to you live. Imagine that, me on stage in your city. Dublin is completely sold out, but everywhere else has got limited tickets left, and you can get yours now at chriswilliamson.live. This is a custom-built live show. I absolutely adore it. I've spent over a year working on it. So if you're a fan of everything Modern Wisdom, come and see me on stage this October around the UK and Ireland, chriswilliamson.live.

    2. DG

      [singing] Well, I'm headed back to Austin, trying to find me again. Something to keep me busy, keep these hands from trembling. Ain't it something like the weather to try and mock my mind. I try to think of something clever to keep me satisfied. Well, I'll take Burnet on the weekend, straight down 29. Past the seaters and believers on a ray and drive. Way to get out of the city and past the smell of the bar. Watch the planes go on by, babe, in the sky, leaving scars. [upbeat guitar] What do you believe in? 'Cause I've been having trouble sleeping. The only thing I'm needing is somewhere I can't find. So I'm headed back to Austin when I close my eyes. [upbeat guitar] Well, if you want me at my best, then I'll proudly hang my dude. Trying to focus what's ahead tonight, winter blues. Takes a simple kind of moment to put my mind at ease. It takes a girl who says she loves me to make me weak in the knees. [upbeat guitar] What do you believe in? 'Cause I've been having trouble sleeping. The only thing I'm needing is somewhere I can't find. So I'm headed back to Austin when I close my eyes. [upbeat guitar]

    3. CW

      That's [clapping] fucking gold. Woohoo.

    4. DG

      Thank you.

    5. CW

      Dude.

    6. DG

      Yeah.

    7. CW

      Unbelievable. So good.

    8. DG

      Thank you very much. Yeah.

    9. CW

      Great to see you.

    10. DG

      That, uh, that one's about Austin, Texas, [laughs] obviously.

    11. CW

      Very timely.

    12. DG

      Yeah.

    13. CW

      Did you write most of Coal in 25 minutes? Is that right?

    14. DG

      Yeah, yeah. Coal, Coal was written one, one of the fastest ones I've probably ever written. Yeah. It, uh, it started... I can kinda show you. So it, it started just with, [upbeat guitar] uh, maybe not this exact chord progression. It was a little bit different. I might have a old video of it I could show you. But I think I almost... I think it started with kinda that hook, the, "They say pressure makes diamonds," how they hit. You know, I was like, "That's, that's great. That's a song. We gotta build around it." And, uh, and then, yeah, verse by verse, and it was just... I remember I was like, had my phone typing on top of our dog kennel in the apartment at the time, and it was, like, right before we, we went out with, like, some work friends. And none of my friends knew I sung, like, at all. I didn't... I don't know. I just don't go around telling people. And, uh, wrote C- wrote Coal, went out, and Julia, my wife, was just stoked on it. She was like, "This is so sick." Um, and she was just showing people, like, Snapchat videos of the song.

    15. CW

      [laughs]

    16. DG

      She was like, you know, just, "What do y'all think about this?" And they're like, "Dylan, you sing?" And I was like, "Cat's out of the bag, I guess." Uh-

    17. CW

      [laughs]

    18. DG

      And then didn't do anything with it for, like, a year or two. So-

    19. CW

      No way

    20. DG

      ... um, until I-

    21. CW

      You sat on that. You sat on a song that did, like, half a billion streams-

    22. DG

      Yeah

    23. CW

      ... for a year or two.

    24. DG

      Well, well, I just... I wasn't, I wasn't, I wasn't on socials. Like, I wasn't putting anything out. Uh, I, I, I didn't do anything until we were on a camping trip, um, with my buddy Caden and his now wife, MK, and my wife and I, Julia. And, uh, I brought my guitar and was just playing some songs. And Caden has, like, the best ear of anyone I know. He's, like, in A&R. That's not- doesn't work in A&R. And he heard Coal, and he's like, "Please sing it again." He, like, voice memoed it, and he's like, "You gotta do something. You have to do something." And my wife was like, "Dylan, you should just post on TikTok." And I was like, "Well, I'm not, you know, I'm not a TikToker." I was like, "I almost can't stand it." Like, I don't... I just... It's not my, it's not my thing. Um, but yeah, I started doing it, and then Coal became this thing [laughs] which is insane.

    25. CW

      One of my buddies, I was best man at his wedding, godfather to his kid, and he was playing We were at a friend's house who has a karaoke machine, and I don't even know why there was a guitar there, and he'd been doing exactly the same thing.

    26. DG

      Mm.

    27. CW

      And I bullied him, bullied him. I was like, "No, come on, come on." 'Cause the choice was between him playing acoustic guitar with a beautiful voice and one of our friends sad emo rapping.

    28. DG

      Oh, yeah.

    29. CW

      And I was like, "Hey, look-

    30. DG

      [laughs]

  2. 9:56 – 18:11

    How to Avoid Getting Lost in the Music Industry

    1. DG

      sure.

    2. CW

      There's a book called "The E-Myth Revisited" by, uh, I think it's Michael Gerber. It's, like, just a business book.

    3. DG

      Uh-huh.

    4. CW

      But it's quite, it's quite well done, and he tells this, uh, fictional story in there of a woman who runs a bakery, and this woman loves making cakes.

    5. DG

      Mm-hmm.

    6. CW

      She loves to do. And she's made cakes for the family, and she makes cakes for her friends, and it's her passion, and she's great at it. Everyone's best cakes. I'm gonna open a bakery. Wouldn't that be cool? Small local bakery. So she opens a bakery, and then it gets popular 'cause she makes great cakes.

    7. DG

      Yep.

    8. CW

      But she needs to hire some staff. Then some staff come in, and the staff start to make some of the cakes and, you know, she's involved in the ingredients and the recipes and the releases, but then there's accounts to do and-

    9. DG

      Yep

    10. CW

      ... she grows a little bit more, and then she gets a factory and, you know, she's spending a little bit less time making cakes.

    11. DG

      Yeah.

    12. CW

      And before she knows it, she hasn't made a fucking cake in years.

    13. DG

      It's, yeah.

    14. CW

      And this, no matter what industry you're in, you have to learn to be able to say no to things or to focus on stuff that previously you would have begged to have had the opportunity to say yes to.

    15. DG

      Yeah.

    16. CW

      I want to be in the room with the A&R person, or y- you're a, a, a writer and you have all of the opportunities to go and do speaking gigs.

    17. DG

      Mm.

    18. CW

      It's like, why were you great as a writer? What made you great as a, a blogger on Substack or as an author that writes books or whatever it is? It was because of the time that you spent, like, stewing in your ideas-

    19. DG

      Yeah

    20. CW

      ... right? Like marinating in this stuff. It was the walk, the three-hour walks that you took with the dog.

    21. DG

      Yeah.

    22. CW

      And all of that time gets squeezed because we can't see, uh, basically, like obvious productivity is really easy to track.

    23. DG

      Mm-hmm.

    24. CW

      How many hours did you spend on Slack today? Or how many-

    25. DG

      Yeah

    26. CW

      ... emails did you send? I've got a full back-to-back day of scheduled calls. This must make me really important.

    27. DG

      Yeah.

    28. CW

      And we go, well, how useful is it for you to go fishing for an afternoon with nothing else happening?

    29. DG

      Yeah.

    30. CW

      You go, "Well, I worked really hard today. I went fishing."

  3. 18:11 – 20:50

    Why Being Unpolished Feels More Authentic

    1. CW

      So, I mean, do you think deliberately looking unpolished is now its own kind of marketing?

    2. DG

      For sure.

    3. CW

      'Cause as soon as you fi- as soon as somebody-

    4. DG

      Mm-hmm

    5. CW

      ... does it on the deck and it's successful, like everything becomes commercialized. Like authenticity is really difficult to survive once a team recognizes it's got commercial value, and then that kind of-

    6. DG

      Sure

    7. CW

      ... kills what authenticity is 'cause people are now performing authenticity.

    8. DG

      Yeah. I mean, I... So that was something... I, I mean, it's honestly, it's still something I obsess over, of like... And I don't obsess over it in a way of like, how do we make this look and feel, you know? 'Cause people are smarter than they ever are. Like, dude, [chuckles] you're not gonna fake it. And people do, and maybe I'm wrong. You know, maybe people do believe a lot of stuff is authentic when it's just absolutely not. But, um, I don't know. I ju- I just feel like I try to stay true to what my mind was thinking when I first got into this thing, of like there's lines I won't cross. Uh, like, but like I would never sacrifice, um... For a while I wouldn't even run ads. I wouldn't do anything. I would not, and I, and I drove my team crazy. And I, and I guarantee I probably took a hit on a lot of things for that, and maybe I was overthinking it. But I was just like, look, I just, I don't want to just all of a sudden, like you said, it's like we know this thing works. I don't want to all of a sudden just dive in. Everyone's telling me, "Well, wait, build-"

    9. CW

      That's the formula.

    10. DG

      Yeah. Here's the formula. Don't po- don't, don't put it out right now. Wait three months. Get your pre-saves up. Post it 30 more times. I posted Coal in total, even like today I think it's been like seven to 10 times ever.

    11. CW

      You're kidding.

    12. DG

      Ever. Now, when it, when it came out, I think I posted it four times, and what people would tell you now is like, "No, you gotta post, you gotta post this on 50-"

    13. CW

      100

    14. DG

      ... times. You know? And it's like, I don't know, it's just such this weird thing in the, in, in music right now where there's so many people doing it, so like you've gotta get out there somehow.

    15. CW

      Mm.

    16. DG

      And you've gotta, you've gotta separate yourself somehow. Like it's, it's even 10X of whenever I, like Coal came out, of like the amount of people kind of playing this type of music. Um, and I, I, I don't know. I, I really don't have the answer to like how to separate, 'cause everyone's doing the authentic thing now, and everything, everyone's doing the polished thing. Like, there's just so many things and-

    17. CW

      I think th- in your world and in my world, um, the ends of the barbell are where people are succeeding. So-

    18. DG

      Yeah

    19. CW

      ... very, very produced, right? Like super, super-

    20. DG

      Mm

    21. CW

      ... polished or very raw and stripped back, and I think the middle is where people seem to go to die-

    22. DG

      Yeah

    23. CW

      ... at the moment.

    24. DG

      Yeah.

    25. CW

      Um, but

  4. 20:50 – 22:47

    Is Country Music Having a Renaissance?

    1. CW

      you're looking at talking about the growth of mu- the music industry. Billboard Top 10 from 2020 to 2023, rap music 34%, country music 7%. '25 to '26, country music 27%, rap music 17%. So rap music's gone in half and country music's four X'd.

    2. DG

      That's incredible. That's pretty crazy. Yeah, I mean, it-

    3. CW

      Wild

    4. DG

      ... I think it's the natural way of things. Like I think, uh, at some point country will be back down and rap will be back up. Like, I mean, that's, that's fine.

    5. CW

      They're the two ends of the-

    6. DG

      You, you know what I'm saying? Yeah. [laughs] Yeah.

    7. CW

      ... stick. [laughs]

    8. DG

      But also like it's, country is not what country was in 2020. Like I, I mean, I hear songs right now that are charting or whatever that I'm like, "That's a great song. I love it. I wouldn't call it country, but sure," you know? Uh, a- you know, it, it's got acoustic guitar in it. Let's do it. Le- that's country.

    9. CW

      Close enough.

    10. DG

      But yeah, it, it's cool. I think, I think at some point it'll go back to s- there, there'll be like a whole new wave of hip hop or something that comes in-

    11. CW

      Mm-hmm

    12. DG

      ... which is cool too.

    13. CW

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  5. 22:47 – 28:07

    Is the Song Actually Good or Just Viral?

    1. CW

      checkout. What's interesting is how virality can reward different behaviors.

    2. DG

      Mm-hmm.

    3. CW

      Because as soon as you find a way to make something become effective, everybody's going to start to play that. I guess, how do you tell the difference between a song that's good and a song that's just algorithm friendly?

    4. DG

      Ooh. I mean, [sighs] I feel like I have a, I feel like I have a bad view on this because I'm in it. So, like I feel like I can pretty easily see when something has something pushing it.

    5. CW

      Mm.

    6. DG

      You know? Like I, I'm, like I, I kind of know what the markers are of like when I hear a song that's trending, and like I'll go look at the audio or whatever, and I'm like, "Okay, they got a team. Like they're, they're running this thing. Like they're-"

    7. CW

      What, what are some of the indications?

    8. DG

      Like, okay, you'll see, you'll see a song come out, and there's 1,000 truck edits to it or something, and I'm like-

    9. CW

      What's a truck edit?

    10. DG

      Like, okay, for, uh, like you'll see, you'll see a new song come out, and it'll be like a video o- of a, an account that all they do is just truck videos with like cool, moody lighting-

    11. CW

      Okay

    12. DG

      ... with lyrics on the top, and they put a song to it.

    13. CW

      I didn't realize this was an ecosystem on-

    14. DG

      Oh, it's not just truck

    15. CW

      ... Instagram. The, the truck-

    16. DG

      There's-

    17. CW

      ... ecosystem-

    18. DG

      [laughs] Dude

    19. CW

      ... truck Instagram ecosystem has got-

    20. DG

      Yeah, that's a big thing

    21. CW

      ... reckon.

    22. DG

      Like, and again, it's a-

    23. CW

      Truckstagram

    24. DG

      ... it's a smart thing because a lot of people follow those accounts for music.

    25. CW

      Yeah.

    26. DG

      So like what teams will do is, you know, they'll, they'll- Pump someone's song on stuff like that. Now, I'll say now more than ever, that doesn't mean that you're gonna have a hit song. It, it might put more ears on it, but like if the song is not that great, and if it kinda sounds like something else, like it just won't... It still won't really catch. But-

    27. CW

      You know, this is the kind of, uh, escalation of firepower when it comes to marketing-

    28. DG

      Mm-hmm

    29. CW

      ... that how much harder is it to break through if every moderately good song has now got an army of clippers and truck edits and-

    30. DG

      Oh, yeah

  6. 28:07 – 32:29

    Why Staying Successful Is Harder Than Getting There

    1. DG

      do.

    2. CW

      Overnight success used to be a bit of an insult, and now it kind of feels like what everyone's chasing.

    3. DG

      Yeah. [laughs] Yeah. Yeah.

    4. CW

      Isn't it strange?

    5. DG

      Very strange. But I, I also think a lot of people aren't ready for it maybe. Like, I mean, I wasn't ready for it, but luckily, like it didn't happen in such a way th- when I was too young, or like it kinda happened like in the perfect moment. Like my wife and I just got married six months earlier, like felt settled down, moved into a house together. Um, and then it happened, you know? And I, uh... Yeah, it... You know, I, I think the hardest part is maintaining it. I feel like that's, that's what does not always happen, is someone will have a really big moment, and you'll know the song. Everyone in the, everyone in the world knows the song, and then in a year it's like they can't sell shows 'cause maybe they just had that one song that was getting pushed out.

    6. CW

      Mm-hmm.

    7. DG

      I don't know. It's, it's a weird world. I, I feel lost in it all the time. That's why I... Dude, I... Like I've deleted so much social media. Any like, like country account out there, I've pretty much just unfollowed.

    8. CW

      Why?

    9. DG

      I, I just, I just... It's just overwhelming. It's just too much.

    10. CW

      What's the s- what's the sensation that you feel when you get exposed to that, when you were getting exposed to that stuff?

    11. DG

      Uh, I mean, my sensation, it's not like I'm like getting anxious or stressed about it. It's more of just like, dude, I gotta have a life outside of... Like everything. Like Instagram used to be like, "Oh, what are my friends posting?" And now it's just like ad, ad, promotion, promotion. Oh, there's my buddy, you know, let me scroll through that p- And it's just... It just gets... And where like when people are like reviewing other country artists, and it's like these people that hide behind us. It's just weird.

    12. CW

      Mm.

    13. DG

      And I'm like... Like it, obviously, it's, it's good for the music industry. It gives a lot of eyes. But as someone that's in the industry, it's like I'm trying to separate a little bit my life and my work, which I feel like I've done a really great job on. Like, again, I'm not, I'm not like very social media forward. Like there... I mean, I've... We have an album coming out, so I've kind of been trying to [laughs] I've j- I'm, like trying to post more, but like, I'm like, I don't know. I don't... I don't know. I don't... You know, it, it, it gets lost out there a lot of times anyways, and it's just- Yeah, it's just a lot

    14. CW

      It's another element of what we were talking about before, that as you become successful, your ability to do the things that made you successful become harder to access.

    15. DG

      Mm-hmm.

    16. CW

      Um, in order for art to imitate life, you have to live a life.

    17. DG

      Yeah.

    18. CW

      This is why comedians, as they get bigger and bigger, all of their acts are about airports and dinners and shows and hotels-

    19. DG

      Mm-hmm

    20. CW

      ... because that's all that they know-

    21. DG

      Yeah

    22. CW

      ... because they're now a big touring act.

    23. DG

      Yeah.

    24. CW

      Every single weekend they're away playing two or three shows.

    25. DG

      Yeah.

    26. CW

      Maybe they're matinee-ing, and all of their friends are in the-

    27. DG

      Mm-hmm

    28. CW

      ... industry as well. And before you know it, you go, "Uh, what is the wellspring that I'm drawing from?" And this-

    29. DG

      Yeah

    30. CW

      ... is the same for anybody. You're a marketer, right? You're, you're a branding person, and you're trying to come up with really interesting insight for a new campaign for a client that you work for-

  7. 32:29 – 37:28

    Inside Dylan’s Songwriting Process

    1. DG

      yeah.

    2. CW

      Where does your process usually start? Is it, like, a line, a melody, an emotion?

    3. DG

      D- it'll be, it'll be stuff... Like, okay, like, I don't know. I'll be on the couch. Julia will be watching TV or something like that. We'll be watching something, and I sing gibberish. Like, I'll try to find a melody that I think is like [singing] But I'm not saying anything. And eventually maybe, like, a word will come to me that it feels very thought-provoking or something. You know? Like, for, okay, for, like, headed back to Austin, the one I played earlier, um, I think it was kind of that line. Like, I knew where I wanted to go, but I didn't have anything, and that just started with, again, me on the couch, probably for, like, 30 minutes. Not because I'm trying to write a song, but it's 'cause I'm just noodling. Like, I don't know. I just like doing it. [guitar strumming] So I start just... Or... And I'll look at Julia like, "That sounds cool." She's like, "Yeah, I like that." And I'll like [guitar strumming] uh, you know. [humming] And then y- you just kind of start gibberish, forming consonants and vowels until they become a word.

    4. CW

      Hang on. So the, the writer's room is you, whatever bullshit's on TV-

    5. DG

      Yeah. [laughs] Yeah

    6. CW

      ... the wife, and presumably now the kid-

    7. DG

      Yeah

    8. CW

      ... who's just, like, flailing in the background.

    9. DG

      Yeah.

    10. CW

      Right? So the difference between this sh- this and a Nashville engine, a little bit different.

    11. DG

      Yeah. Very. But that's why, like, uh... And ag- again, I have, I have nothing against those guys. They're very talented in their own right.

    12. CW

      Fucking animals, all of them.

    13. DG

      It's, it's incredible what they can do, but it just doesn't... I can't do it. That's like I said-

    14. CW

      Have you tried? Have you tried to be in the, like, the engine like that?

    15. DG

      No. No. I've-

    16. CW

      Interesting

    17. DG

      ... I've... The closest I've come to that is, like, I write with my brother, uh, or, like, multi-instrumentalist, Colton. Um, and even then, it's just different. It's a whole different way of writing. Um, I can't say if I like it more or less. Like, I, I, I still think just me on my couch in my living room, usually at night, is like, that's where I get the stuff I like. Like, but then it, like... My brother has a song, uh, that he wrote called Ramblin, and it's on the album, and it's actually the title of the album, Ramblin. Excuse me. Um, and it's, like, one of the best songs on the album. Like, it's written so cool, and all I did was write, like, the chorus and a little, like, melody for the chorus.

    18. CW

      Can I hear a bit?

    19. DG

      Yeah. Uh, he's way better at playing it on guitar, so I'm probably gonna butcher it. [guitar strumming] Also, I haven't played it in so long. Jeez. Listen to the wind, calls me by name. Same old dirt from where I was raised. Ain't no ramblin' man oughta cause all this pain. Listen to the wind. Listen to the wind. No. Listen to the wind, it calls me by name. Like, I don't know. It-

    20. CW

      So cool

    21. DG

      ... it's v- it's a beautiful song. I butchered it. Sorry, Blake. He's probably listening, and he's like, "You messing up my song bad."

    22. CW

      Fuck, idiot.

    23. DG

      Um, but yeah, no, he, he does this, like, finger-picking style that, like, I just can't even do, and, um... 'cause he's, he's a way better guitar player than I am. But, um, this is so cool. Like, that's the stuff that I love. Like, I, I'm not... I, I was early on, but especially, like, now, like, I'm very open to collaboration and, and I'm not as, like, sacred about every word's gotta be mine. Like, I, you know, I, I'm very... Writing is my passion almost more than singing. So, like, I, you know, I'm very particular of, like, what I want the songs to say and sound like, and I don't know. I just like, I like writing.

    24. CW

      Would you ever do it for someone else?

    25. DG

      I think so But it's h- maybe. I don't think I could write, I don't think I could write a song for someone else that I think that I could sing.

    26. CW

      Mm.

    27. DG

      Because I just wanna sing it.

    28. CW

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  8. 37:28 – 51:02

    Do Artists Still Write Their Own Songs?

    1. CW

      Well, I had, uh, Bellion on the show last year, and he's just so fucking g- I mean, there was a guitar in the backside of the room, and I'm thinking, "Okay, John motherfucking Bellion"-

    2. DG

      Mm.

    3. CW

      ... okay, right? I, uh, uh, gestured to a guitar like, "Hey," you know, "Explain how he did," and he looked at it. He goes, "I don't know how to play that thing."

    4. DG

      No way. Okay.

    5. CW

      So I go, yeah, well, he's like, "I fucking... It's not my, it's not my bag."

    6. DG

      Yeah.

    7. CW

      "Like, I'm just here to do the thing."

    8. DG

      Yeah.

    9. CW

      But he was telling me about how he'd taken all of his time off, five years maybe-

    10. DG

      Mm-hmm

    11. CW

      ... this big break away from producing any m- uh, publishing any music himself, and he just wasn't fussed.

    12. DG

      Yeah.

    13. CW

      He'd had this altercation, pretty public altercation, I think, with his label. Didn't wanna... "I'm not gonna play the game. Just gonna make music for other people, and this will be great." And he's just creating banger after banger. And I said, "Well, how did you know that you wanted to get back into making music again?" He said, "Well, when I had my stack of tracks to show whichever artist was coming in," like little demos and stuff that I'd cut together for them to have a little listen to, "I'd find myself, you know, going down, going down, and then I'd, I'd double tap over the top of a couple of them."

    14. DG

      Mm.

    15. CW

      And he's like, "That one's for me."

    16. DG

      Yeah.

    17. CW

      And he could f- hear in the back of his mind this bit of almost kind of selfishness or maybe a bit more swagger or kind of, you know, ownership coming back in-

    18. DG

      Yeah

    19. CW

      ... 'cause he wanted to do that. But yeah, I, I think about, um, a lot of my friends that are writers, you know, they do versions of ghostwriting for people-

    20. DG

      Mm

    21. CW

      ... and they'll shape ideas, and then sometimes they'll come up with the synthesis of an idea. And every so often they put out one, they feel a little bit aggrieved that they didn't get to put it under their own name. And the same goes for comedy writers.

    22. DG

      Yeah.

    23. CW

      You know, all of the roasts that you see, every big roast that you see online, th- a lot of comedians now are opening up in the caption of their Instagram post if they put one of these huge, big, like, you know, clips up that-

    24. DG

      Yeah

    25. CW

      ... completely rips. They put the credits in there of all of the writers that have contributed.

    26. DG

      I did not know that.

    27. CW

      It's not them. I'm right here, right, Jared? Like, this is the-

    28. DG

      Well, 'cause I, I always thought it was like, I always thought it w- it was like rap and comedy... Like, like country was like the... Country and pop were like, they had writers. But I thought it was-

    29. CW

      Writer origin.

    30. DG

      Yeah. I, I thought like, I thought like rap, comedy was more like you are what you write.

  9. 51:02 – 1:01:16

    Why We Shouldn’t Always Take Shortcuts

    1. CW

      The decision that everybody's gonna make is, okay, do I want to do the harder thing?

    2. DG

      Mm-hmm.

    3. CW

      And it's weird because do hard things is kind of this tagline that everybody likes to lean into.

    4. DG

      Yeah.

    5. CW

      The 4:30 AM cold plunge and the runs and the weightlifting and the, you, you sticking to your diet. But the decision of do I want to do the harder thing or the easier thing is gonna encroach into every area of life.

    6. DG

      Mm.

    7. CW

      It's gonna encroach into whether or not you want to ord- Look, if you one click order flowers that goes to your missus' door-

    8. DG

      Mm

    9. CW

      ... because she's having a hard day, or if you drive to the fucking florist and pick them up and hand deliver them to her-

    10. DG

      Yeah

    11. CW

      ... there is just a, there is a, a, a explicit real world difference-

    12. DG

      Yeah

    13. CW

      ... right? A tangible difference between those two things. But as things, convenience begins to encroach on the rest of life, everybody's gonna have to make that decision for more and more and more stuff.

    14. DG

      Y- oh, yeah. It like, yeah, I hear what you're saying. It's, it's not... I saw this one picture where it was like it started as sit down restaurant, it turned into drive-through, and now it's Uber Eats.

    15. CW

      Mm-hmm.

    16. DG

      It, you know, it was movies and then it's YouTube and now it's YouTube Shorts.

    17. CW

      Mm-hmm.

    18. DG

      Like it just, it just keeps going. Yeah, and it just keeps expanding.

    19. CW

      It's derivative. It becomes distilled down.

    20. DG

      Yeah. And it's like even, I mean, I, I find myself, I used to never do this, but I found myself literally this week and I, uh, of, I was watching an Instagram reel and I was wa- I was watching it, and I was like, "Let me hold down. Let me go times two speed here." You know? And I'm like, "What am I doing?" Like I just [inhales] ...

    21. CW

      I need to-

    22. DG

      And again, it's like-

    23. CW

      I need to speed fuck myself and get that algorithm harder

    24. DG

      ... yeah, yeah.

    25. CW

      Yeah.

    26. DG

      And it's like, and it's like you're saying, it's not just that. That might not be the bad thing. I don't know, maybe you're, you're, you're on, you're on a bathroom break and you're like, "I don't know. Get, get to the point." You know? [laughs] I, you know, I get that. But it starts creeping into everything. 'Cause yeah, 20 years down the road, you know, with, with a, with a musician and they're like, "All right, I gotta pay the bills. We need a new song. I just don't have it in me." What... Write a song.

    27. CW

      Yeah.

    28. DG

      It's pretty good. It's gonna sell. Like what's, what's stopping people from doing that if it's just every, every year it's just one extra thing-

    29. CW

      Yeah

    30. DG

      ... you know?

  10. 1:01:16 – 1:03:08

    Is Emotion the Secret to Dylan’s Music?

    1. DG

      I don't know.

    2. CW

      It seems like, uh, you take a very sort of emotionally informed approach to music.

    3. DG

      Mm-hmm.

    4. CW

      It's quite self-deprecating-

    5. DG

      Mm-hmm

    6. CW

      ... sort of stark sometimes-

    7. DG

      Yeah

    8. CW

      ... I think. Is that fair?

    9. DG

      Yeah. Uh, I think, I think it kind of depends. Like, and I also think it really changes the mood of the song itself. Like, uh, I don't know. I, I find those songs can be easier to write. I feel like when I write my happy songs, they come off cheesier. When I, when I feel like it's the same level of lyrical writing, um... Dude, and it's also, yeah, it also... If I put, if I put Coal on, like, an EDM track, I guarantee people would be like, do we... They wouldn't really care about what the lyrics are. Again, it's like, doesn't feel sad.

    10. CW

      Yeah.

    11. DG

      It's like, have you seen, have you seen people that play, like, ballad piano, like the Drake & Josh theme song?

    12. CW

      [laughs] No.

    13. DG

      And it, it sounds like a beautifully written song, and you're like, "It's kind of deep."

    14. CW

      Mm.

    15. DG

      Like, it's kind of a sa- you know, what- whatever. But it's like, it's all how it's framed. I, I, I think... I mean, I think of, like, Jason Isbell when it comes to this, but if you put his type of lyricism into his type of guitar playing and his voice and the raspiness, like, it's gonna come off that way-

    16. CW

      Yeah

    17. DG

      ... um, whether it's intentioned to be or not. Or then you, you can go listen to, like, a Turnpike song, who I think is some of the best writers in the world, but maybe they're four on the floor, and it's kind of a more upbeat groove, but he's talking about how, like, "My dad's gonna whoop my ass if I'm ever back in this county." Like, it's, it's might be a sad feeling song or whatever it is. I'm not trying to say that song specifically, but, um, and it feels upbeat. You're like, "Oh, I can get down to this party." You know? It's a good time. So I think-

    18. CW

      Yeah. Forget the, forget the lyrics or remember.

    19. DG

      Yeah, I think, I think it's, yeah, I think it's sometimes the way that it's played on the guitar, you're playing different, like, minor chords and stuff like that. Um, but I, I like to lean into that. Like, I feel like I love listening to music like that. Even when I'm, like, happy, I'll be, I'll be the happiest guy in the world, and I'll be like, "Let me put on a sad one. Let me put

  11. 1:03:08 – 1:09:24

    Why Sad Men Are Taking Over Country Music

    1. DG

      on a slow one."

    2. CW

      Why do you think male sadness is dominating modern country?

    3. DG

      I think, I think two things. Uh, I think for one, um, I think it's the only place where I feel like a lot of guys, a lot of males, um, feel like they're allowed to talk about it, like, without being, without... You know, like for example, if I went up to, like, my buddies or in our group chat and said how I felt in Coal, it would come off of like, "Like, brother, get it together. What are you talking about?" But you put country music behind it, and it's like, "Dang, that's a beautiful song. I actually connect with that, but I'm not gonna, like, say I do." You know? It, it feels like it's guys', uh, almost like a dude therapy session, and I think that's why so many people write about it is that it connects really deeply. It almost like, it says the feelings that a lot of these dudes, I think, feel, but they're like blue collar fellas. They're like, "I'm not telling, I'm not telling nobody how I feel." But like, dude, when... At our shows, the, the people who are s- like heart and soul singing it out there in the crowd are the, are the dudes. Arms around each other. The, I promised they would leave that show, and they would never tell each other about their feelings. But they come to the show, and they're looking at each other screaming these lyrics, and it's like, yeah, it's like cathartic. It's like, it's their-

    4. CW

      Mm.

    5. DG

      It's like a thing. So I think, I don't know, I think it just comes off well. It's like the way to, way to do it as a dude-

    6. CW

      I wonder if it's-

    7. DG

      ... without still being cool [laughs] you know?

    8. CW

      I wonder if it's a weird comment on masculinity that men feel comfortable seeing their emotions reflected in lyrics but uncomfortable exposing them in daily life.

    9. DG

      Mm.

    10. CW

      It's like, this guy has said this thing that I feel. He's put words to it. I'm happy to sing it.

    11. DG

      Yeah.

    12. CW

      I'm happy, I'm happy to sing it at his show-

    13. DG

      Yeah

    14. CW

      ... and I'm still... It, it feels like there is room for that. It's a, it's a really interesting sort of balance between those two things.

    15. DG

      Yeah. It, and it almost, it almost feels like sometimes the opposite for women. Like, it almost feels like-

    16. CW

      Female songs are empowering, and male songs are about vulnerability.

    17. DG

      Yeah, but, but and it's, and it's the opposite too, where it's like when women sing about vulnerability, almo- it's almost like the male crowd is like, "Here we go. Another, you know, another female country artist talking about her breakup."

    18. CW

      Yep.

    19. DG

      But it's like when guys do it, it's like, "Brother, I'm, you know, [laughs] I got you."

    20. CW

      [laughs]

    21. DG

      So it is. It kind of feels like that's, that's the male outlet sometimes-

    22. CW

      Mm

    23. DG

      ... is like through music. And then I feel like the girl outlet, again, I'm, I'm not trying to be the guy speaking on behalf of all the women out there. I would never [laughs] do that. But-

    24. CW

      Yeah

    25. DG

      ... um, yeah, it kind of feels like it's the opposite, where it's, you know.

    26. CW

      I thought-

    27. DG

      I don't know. Maybe I'm wrong

    28. CW

      ... I thought, uh, I Sit in Parks by Kelsea Ballerini was such a fascinating fucking concept for a song.

    29. DG

      I, I haven't heard that.

    30. CW

      Oh, dude. So it's her talking about, um, a relationship that she used to be in, and she didn't go through with it because her partner wanted to have kids, and she wanted to focus on her career.

  12. 1:09:24 – 1:14:52

    The Hardest Emotions to Turn Into Music

    1. CW

      What, uh, what emotions have you found to be the hardest to write about?

    2. DG

      Ooh. Probably, like, happy, I think. And, uh, not, not in a way it's like, "Oh, man, I can't write about being happy," 'cause I can, but I feel like it, it doesn't come off the tongue as easy as, like, as, like, a sadder, more heartfelt song. I feel like I can really paint that picture versus, like, when I'm singing a song... And, and maybe, like, and I mean, like, happy. I don't mean, like, love. I feel like I can write really well about lo- I, I feel like I can write about my wife, like, a lot.

    3. CW

      Yeah.

    4. DG

      I have. I've written a ton of songs about her, and I feel like those are some of my favorites I've ever written. Um, but I'm talking about just straight up, this one's gonna come in, come, come on in the bar.

    5. CW

      Yeah.

    6. DG

      I struggle with that. Um, I don't know why. I, I think some people nail it, and I've just... I, I, I'm, I can't. It's not always there.

    7. CW

      Mm.

    8. DG

      Yeah.

    9. CW

      I, I mean, I spoke to Dan + Shay about this. Luke Combs, fucking unbelievable.

    10. DG

      Mm.

    11. CW

      Like, got as much swagger as it's possible for a white guy to have.

    12. DG

      Yeah. [laughs] Yeah.

    13. CW

      Like, he's the blackest white guy-

    14. DG

      Yeah, yeah, yeah

    15. CW

      ... that you can think of.

    16. DG

      Yeah.

    17. CW

      And, um, but when you think about the, that sort of arc over the last, what, decade or so-

    18. DG

      Mm

    19. CW

      ... of his, of his songwriting, you go from very sort of tortured, uncertain, tumultuous, this crises, and now there's a bit of me that wants him to smoke some crack.

    20. DG

      Yeah. [laughs] Yeah.

    21. CW

      There's a bit of me that wants him to, like, have that friction again in life-

    22. DG

      Mm-hmm

    23. CW

      ... because, yeah, things are going well, and my son misses me when I go away, but I do come back, and, like, my dad's getting older.

    24. DG

      Yeah.

    25. CW

      And that's gonna be hard when it doesn't happen. And he's still fucking ripping it.

    26. DG

      Yeah.

    27. CW

      But how much harder you have to work-

    28. DG

      Mm-hmm

    29. CW

      ... to make a banging song when you don't have that friction in your life.

    30. DG

      Yeah.

  13. 1:14:52 – 1:22:59

    Don’t Lose Yourself Chasing an Audience

    1. DG

      sick.

    2. CW

      I wonder whether there's any emotions that you want to sing about, but you don't think that the market has an appetite for.

    3. DG

      Hmm. I mean, okay, here, here's a great example, and I know a lot of artists struggle with this. I'll play an acoustic song on my back porch, and I'll play it a certain way, but I know the studio's different. Studio version's different. It's got some drums, has a little, you know, slide maybe in it. It's just kinda more upbeat, and then you'll put out that version, and everyone's like, "Just, just don't change it."

    4. CW

      Give me the porch version.

    5. DG

      Give me the por- you know. And it's like, I think you have to try to expand your sound. Like I, I was watching that Billy Joel documentary. So cool, by the way, if you haven't seen it.

    6. CW

      No.

    7. DG

      It's like five hours long. It's incredible.

    8. CW

      Right.

    9. DG

      His life is just... It's what the heck. But he always made it a point to change the way his sound was. Bob Dylan did the same thing where he went to the Newport Folk Festival, and everyone was like, you know, "Get your harmonica out," and he's like, "I wanna play an electric guitar." And it- it's, it's, uh, you feel like you don't wanna get trapped in, like, your own trope. Like I, I'm not trying to get trapped in this, like, I'm an acoustic guy. I'm gonna sing about how hard my life is.

    10. CW

      Yeah.

    11. DG

      And... But you also want to service the people who listen to your music the most. Like, you know that's what they want, and that's... And it's like, y- yeah, it's this, it's, it's like this push and pull thing. So I, I feel like, feel like I've done the best job that I can. Like, I don't really put too much pressure on. I'm still making music that I love. I really not, I don't try to overthink it.

    12. CW

      Yeah.

    13. DG

      Um, but yeah, I know a lot of artists that fall into that thing where it's like, "I wanna put out different music, but I just know it's probably not gonna do well. And if I do it, if I put out this song, it'd probably do a lot better because that's what I'm known for. That's what people wanna hear."

    14. CW

      You know the idea of audience capture? Have you heard of that?

    15. DG

      Uh-uh.

    16. CW

      Okay, so it's from my world's, uh, content creation, YouTube. Um, you test the ground with a bunch of different content. Maybe you start to pick up a little bit of speed.

    17. DG

      Mm.

    18. CW

      And then you find something that hooks a bit. You start talking about, uh, politics, but you talk about it from a libertarian lens, and you're, you're sort of, you're maybe a bit more bombastic than you used to be.

    19. DG

      Yeah.

    20. CW

      Oh, wow, they like that. Oh, well, I, I've been rewarded for that.

    21. DG

      Mm.

    22. CW

      I'll, I'll go again, and you get a bit more bombastic, and you get a bit more bombastic.

    23. DG

      Yeah.

    24. CW

      And before you know it, you're, like, peak Alex Jones.

    25. DG

      Yeah. [laughs]

    26. CW

      You know?

    27. DG

      Yeah.

    28. CW

      Sort of shouting and screaming and, and-

    29. DG

      Yeah

    30. CW

      ... and doing the thing, and you begin to throw red meat to your audience, and instead of creating what you want to create, you give them what you think they want.

  14. 1:22:59 – 1:29:23

    A Snippet From Dylan’s New Album

    1. CW

      All right, dude, let round this out. What's your... Give us a little something from the, the new album, whatever you like the sound of.

    2. DG

      I'll play, I'll play a song called Clothesline. Um, [guitar strum] should I sing this one? Yeah, this one's good. I think this, I think this is gonna be a single maybe. I don't know.

    3. CW

      That's something you could do this afternoon.

    4. DG

      But no, but I do it on purpose. I, I... But this, I guess this is what I'm talking about. Like when I, I... Yes, I could choose the singles and have it all on a calendar and rock it and just go, but I, I don't... Again, I, I think this is something that I probably, I struggle with, is kind of the system formula thing. I don't know, like I, I, I would rather go like week by week or like feel it out. I don't know. Yeah. I, I don't know. I, I, I, I, I think it's gonna be a single.

    5. CW

      All right.

    6. DG

      But again, I, I also... Actually this, and I will... I'll, I'll sing it right after this, but this brings me back to a point that we were talking about earlier, uh, about like teasing music and crowdsourcing and being like, "What song does better?" Like a- there's a part of me that misses the way of like when an artist puts out an album, you don't know what the songs are.

    7. CW

      They've not Waterfall released five in advance.

    8. DG

      Yes. You don't know what the songs are, and you are stoked to dive in.

    9. CW

      Yeah.

    10. DG

      And I'm trying to play this middle ground of like, okay, business-wise, yes, we should be teasing songs and, you know, getting people excited, and I'm not saying it's a bad thing, but there's a side of me that's like, man, wouldn't it be great just to give fans just 12 new songs that everyone can be excited for? And you have no idea what it sounds like. It might be a whole new sound. Like that's kind of what used to happen, or like, I don't know, like I just think that side of it's cool. Like my favorite thing, I know I brought them up a lot, um, but Turnpike, when they dropped Price of Admission, they did no singles. All they did was put up a billboard in the middle of the desert and was like, "Album's out in two weeks." I think that is so cool. Now, I'm not saying everyone can do that. Like-

    11. CW

      Algorithmically might not be the most-

    12. DG

      Exactly

    13. CW

      ... effective way to do it-

    14. DG

      Yeah

    15. CW

      ... but it's sick.

    16. DG

      But yeah, and that... But that's where like as an artist, you have to kinda weigh your options between, you know, like we said earlier, like what's authentic, and at the end of the day, like what is going to

    17. DG

      ... get people this music. Like what's going to pay the bills and do, you know, there's a fine line, so.

    18. CW

      Unreal.

    19. DG

      But anyways, uh, this one's called Clothesline. I haven't played this one in a while. I'll, I should... I'll, I'll remember it. That's another thing, I'm bad with lyrics, but.

    20. CW

      [laughs]

    21. DG

      [guitar playing] Oh, wait, am I plugged in? Yeah, I am. Cool. [laughs] Uh, this one's called Clothesline. [singing] Baking soda on the bed sheets. Make 'em smell brand new. I'm sleeping in and I'm going out. Trying not to think too much about you. Don't call me later when my light's off. I know just how you do. You call me once, but yeah, my door later. In the morning you'll be gone too soon. 'Cause I know you're just gonna hang me out to dry. So close to being left on that clothesline. Oh, second guessing's always left in this old heart of mine. Baby, I know you're just gonna hang me out, hang me out to dry. Out to dry. So stopping early at yellow lights. Said it ain't worth the risk. You used to tell me that I'm moving too fast with your hand tied around my wrist. So treat me like it was years ago. Before you changed your mind. Said I was nothing but a hopeless old lover and baby, maybe you'd be right. I know you're just gonna hang me out to dry. So close to being left on that clothesline. Oh, second guessing's always left in this old heart of mine. Baby, I know you're just gonna hang me out, hang me out to dry. Out to dry. Now I know you're just gonna hang me out to dry. So close to being left on that clothesline. Second guessing's always left in this old heart of mine. Baby, I know you're just gonna hang me out, hang me out to dry. Out to dry.

    22. CW

      Let's fucking go. Dylan Gossett, ladies and gentlemen.

    23. DG

      Thank you.

    24. CW

      Dude, you rule.

    25. DG

      Thank you.

    26. CW

      Congratulations. New album's out when?

    27. DG

      September 25th.

    28. CW

      Fuck yeah.

    29. DG

      Yeah, so.

    30. CW

      Appreciate the heck out of you, man.

Episode duration: 1:29:23

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