Chris WilliamsonHow To Make Your Creativity Beat The Algorithm - Dylan Gossett (Live Performance)
Chris Williamson
Live performance of Cole 0:00
Dylan Gossett opens with a live rendition of his song, which he describes as being about heading back to Austin, Texas, and dealing with restless nights and trying to find clarity. The performance is followed by warm applause and a quick exchange with Chris Williamson about the song's origins.
Writing Cole in minutes 4:03
Dylan explains that Cole came together fast, starting from a single hook, the line about pressure making diamonds, which he built the rest of the song around verse by verse. He wrote it on his phone on top of a dog kennel in his apartment before going out with friends who had no idea he sang, and his wife Julia shared it on Snapchat, which is how his secret got out.
Sitting on the song 5:03
Despite the strong reaction, Dylan did nothing with Cole for a year or two because he was not on social media and disliked TikTok. The turning point came on a camping trip when his friend Kaden, who has a strong ear for music, heard him play it and insisted he had to do something with it, which eventually pushed him to start posting.
Life during the racetrack job 6:30
Dylan recalls that he wrote Cole while living in Austin and working in event operations at the Circuit of the Americas racetrack, starting as an intern and living out of his parents' RV trailer for months. He describes the period as a tough, grinding stretch, especially during F1 season with twenty hour days, mixed with some inner family struggles, though he stresses he was not at the lowest point of his life, just going through everyday struggles like anyone does.
Feeling stuck while building up 8:00
Chris relates this to a pattern where people put in effort without seeing results, comparing it to pulling back an elastic band repeatedly before any release happens. He points to Cole's top YouTube comment, which says the song captures the feeling of working on yourself and making progress while still feeling lonely and like a failure, and Dylan agrees that captures exactly how that period felt.
Music as a business 9:32
Dylan reflects that without the racetrack job and those real world experiences, he could not have handled being thrown into the music industry, and that being an artist involves far more business management than people assume. Chris connects this to the story from the book The E Myth Revisited, about a baker who loves making cakes but ends up running a factory and no longer bakes at all, illustrating how growth can pull people away from the very thing they loved doing.
Guarding time for real work 10:31
Chris argues that people must learn to say no to opportunities they once would have begged for, because the quiet, unmeasured time, like long walks or an afternoon fishing, is often what produced the good work in the first place, even though it looks unproductive compared to a packed schedule of calls and emails.
Changing expectations over time 12:00
Dylan notes that when he wrote Cole he had no expectations and was simply following his passion, but now, years and several albums later, he judges his own work far more harshly and would not release that original demo version today, recorded on his laptop on the edge of his bed with uneven levels that later needed remastering.
Staying grateful amid new struggles 13:01
Dylan admits the music industry has real struggles but insists he will never be ungrateful, since a few years ago he would have loved to have problems like stressing over an album release or signing vinyls in Nashville. Chris links this to hedonic adaptation, the way people quickly get used to new comforts, whether a new car or a bigger team, and start treating what used to feel like a dream as just another burden, such as needing a guitar tech at soundcheck.
Revisiting old worries 14:30
Chris wonders aloud what it would be like to revisit the exact texture of one's mind from years earlier, and Dylan responds by recalling that his worries back then were about money and simply making it through his shifts at the racetrack, setting up a return to playing another verse of Cole.
Why he didn't cut the hook early 15:31
Dylan explains the thinking behind his song Cole, where the payoff line does not land until the second time the pre-chorus comes around. He hated the era of fifteen-second TikTok clips built around pre-saves stretched out for months, and he believed the strength of the song was in the writing rather than a quick hook. He kept the line about seeing heaven without dying and meeting the devil without trying because he was proud of the writing, even though a shorter clip would likely have pulled more views. He also notes how much luck was involved, since he only posted the song a handful of times and things might never have taken off if a different take had been chosen that day.
Authenticity becomes its own performance 20:30
Asked whether looking deliberately unpolished has become a marketing style in itself, Dylan agrees that once a team spots commercial value in something authentic, people start performing authenticity rather than living it. He says he refused to run ads for a long time and avoided formulas like stacking pre-saves and reposting a song dozens of times, even though it frustrated his team. He estimates Cole has only been posted seven to ten times ever, compared to the now-common advice to post a song fifty times. The two of them agree that success now clusters at the extremes, either very polished or very raw, while anything in the middle tends to get ignored. They also compare genre growth on the Billboard top ten, noting rap rose sharply from 2020 before falling back by the mid-2020s while country climbed from seven percent to twenty-seven percent over roughly the same stretch.
Marketing armies and the ticket squeeze 22:59
Dylan describes spotting when a song has an industry push behind it, such as a wave of moody truck edit videos or boat edit accounts that pair trending lyrics with a track to build an audience. He says this kind of push can put more ears on a song but will not turn a mediocre one into a hit. The conversation shifts to touring, where he says ticket sales, not viral moments, have always been his measure of success, even as rising costs and packed touring schedules make that harder. They discuss blue dot fever, where big-name artists fail to sell out arenas, tied to inflated ticket prices, Ticketmaster and Live Nation pricing pressure, and fans choosing cheaper new acts over familiar names. Dylan adds that sudden fame is hard to sustain and that he has deleted much of his social media to separate his private life from the promotional noise of the industry.
Losing Touch With Your Wellspring 30:31
Dylan talks about how big touring acts end up writing only about airports, hotels, and shows because that becomes their whole world, surrounded only by industry friends. He draws a parallel to any creative or marketing professional who only consumes work from people in their own field, asking where new inspiration is supposed to come from if you spend all your time talking to marketing people about marketing. He mentions once wanting to be the kind of fan of his own music that he used to be, and admits that success can push you further from your original perspective, quoting Miley Cyrus on needing time off the road just to actually live.
Writing By Gibberish On The Couch 32:31
Dylan describes his actual writing process as starting on the couch, often while his partner Julia watches television, humming gibberish melodies until real words start to form from the consonants and vowels. He gives the example of his song "Headed Back to Austin," which began this way, just thirty minutes of noodling rather than deliberate songwriting. He contrasts this loose, private method with the more structured, multi-writer approach used in Nashville, saying he has tried co-writing with his brother Blake and multi-instrumentalist Colton, but still prefers his own late-night couch process, even though he performs and praises Blake's song "Rambling," the title track of the album, which Blake wrote almost entirely himself.
Ghostwriting Across Music And Comedy 37:01
The conversation shifts to how much creative work is actually ghostwritten, using John Bellion's return to releasing his own music after years of writing for other artists as an example, where he realized certain demo tracks felt like they belonged to him rather than the artist he was writing for. This leads to a broader point about comedians, where it's estimated that less than ten percent of touring comedians perform entirely their own material, with some now crediting writing teams in social media captions for viral roast clips. Dylan reflects that his own sense of ownership centers on the words themselves, saying he has only once accepted a fully outside song, his brother's "Rambling," and that he resists needing help finishing a chorus or bridge because he wants to complete his own thought. The discussion then turns toward AI's growing role in writing, introducing the psychological idea of the fading affect bias, where bad memories fade faster than good ones, and how this connects to a friend's story about doubting a past decision to leave a relationship, ending with a personal account of choosing not to let ChatGPT finish a half-written essay.
The pull toward AI assistance 45:00
Dylan and the host describe how AI now begs to help with everything, from summarizing messages to writing replies, and how that constant offer creates a strange yearning to actually use your own mind. Dylan compares this to being on autopilot while touring, doom scrolling and feeling like he is getting cognitively lazy rather than exercising his thinking. He connects this to why people dislike participation trophies, arguing there is no better feeling than earning a win after genuinely failing and trying again, rather than being handed success.
Hard wins versus easy wins 50:01
Dylan quotes a line from Mark Manson that he has been fixated on this year, about doing hard things not because they are fun but because the win actually means something, since you bled and broke for it, and easy wins are forgettable while hard ones change you. He argues this is the choice everyone will face with AI, even in small moments like writing a thank you letter by hand instead of typing it into a service like Moonpig, since a handwritten note shows effort and love in a way a printed one cannot. Both agree AI has a place in ordinary technological progress, but the line matters most where something is artistic or sentimental, because art depends on imperfection and letters are meant to carry emotional effort, not just words on paper.
Convenience creeping into music 52:02
They trace how convenience keeps expanding, from sit down restaurants to drive-thrus to Uber Eats, and from movies to YouTube to YouTube shorts, noting people now watch reels at double speed without realizing why. They discuss how recording technology changed music, from splicing tape by hand fifty years ago to now being able to comp a perfect take pluck by pluck, and how imperfections, like a hat falling on piano keys on an old Elton John record, used to give songs life until authenticity itself started becoming manufactured and marketable. Dylan reflects that music has long involved teams and ghostwriters, so ownership was already fluid, but worries this fluidity becomes a slippery slope as one-click mastering and AI-assisted songwriting make it harder to say where a song truly originated, especially once labels start chasing whatever formula seems to work, as with the band Geese and their reported use of a mixing and mastering engine behind a hit.
Knowing When AI Crosses a Line 59:02
Dylan Gossett says the question of using AI in songwriting comes down to gut instinct rather than fixed rules. A kid at home looking up a word or a rhyme has no intention of hiding anything, which is different from someone trying to squeeze as much AI help as possible while hoping nobody notices. He compares this to older debates about producers and engineers using new tools, like chaining synths together or using a drum machine, and concludes that either you are making the music or something else is making it for you.
Why Sad Songs Feel Truer 1:01:00
Gossett explains that sad or emotionally stark songs are easier for him to write and feel more authentic, while happy songs risk sounding cheesy at the same lyrical level. He points out that the same words can land completely differently depending on framing, comparing Jason Isbell's raspy, aching delivery to a Turnpike Troubadours song that sounds upbeat and danceable despite lyrics about a father threatening a beating. The conversation turns to why male sadness dominates modern country, and Gossett argues country music gives men a rare, accepted outlet to express feelings they would never voice to friends, describing shows where men sing along arm in arm with real emotion despite never speaking about feelings otherwise. He and his host discuss how women's songs often lean toward empowerment while men's lean toward vulnerability, using Kelsey Ballerini's song about doubting a career choice over having a family as an example of a more complex female counterpoint, and they note that framing emotion inside a song acts as a kind of safe distance or defense mechanism for men who wouldn't otherwise open up.
Struggling to Write Happiness 1:09:33
Asked which emotions are hardest to write about, Gossett names plain happiness, distinguishing it from love, which he feels he writes well, including several favorite songs about his wife. He notes some writers seem to nail upbeat, bar-anthem type songs naturally while he cannot always find it. The conversation turns to how a stable, happy life can make it harder to write compelling songs, since audiences resonate with pain, prompting Gossett to describe his love of storytelling through invented characters, citing his song Lonesome Cowboy about a man who kills someone and goes on the run, and older Western ballad traditions like Marty Robbins' gunfighter songs. The segment closes with a story about Dolly Parton's Jolene, said to be inspired by a real bank teller who flirted with Dolly's husband, with the name borrowed from a fan Dolly met at a party.
The Jolene and I Will Always Love You story 1:13:30
Dylan tells the story behind Dolly Parton writing both Jolene and I Will Always Love You on the same day, inspired by an eight-year-old red-headed fan whose name she borrowed for Jolene. He notes Whitney Houston's version of I Will Always Love You spent fourteen consecutive weeks at number one, a record only recently matched or passed, possibly by an artist named Ella.
Balancing the acoustic sound with studio changes 1:15:00
Dylan explains the tension between playing a song simply on his back porch and giving it a fuller studio treatment with drums or slide guitar, since fans often push back and ask him not to change it. He points to Billy Joel and Bob Dylan going electric at Newport as examples of artists who evolved their sound despite resistance, and says he tries to balance expanding his music with still serving the listeners who already love him, without overthinking the formula.
Audience capture versus criticism capture 1:18:00
The host explains audience capture, a concept from online content creation where a creator keeps escalating toward whatever gets the strongest reaction, using the example of someone drifting into ever more bombastic political rhetoric until they resemble Alex Jones, and warns that creators who do this eventually resent the audience because they've betrayed themselves for a projection. He contrasts this with criticism capture, coined by Ethan Strauss, where people act to avoid or preempt criticism rather than to please, either by over-caveating everything or by aggressively shadowboxing imaginary critics.
Instant feedback and modern pop production 1:20:32
Dylan notes how social media gives artists instant feedback the moment they leave the stage, which adds pressure that didn't exist before. The pair then watch clips contrasting a stripped-down Morgan Wallen stadium performance with a highly polished, heavily choreographed Tate McCrae show, prompting a discussion about how live production keeps escalating, referencing acts like Justin Bieber, NSYNC, Backstreet Boys, and MGK's return to full dance numbers as part of a recurring cycle where old styles come back as new.
Withholding music from teasers and algorithms 1:23:00
Before playing a new song called Clothesline, Dylan says he resists scheduling singles too formulaically and prefers to feel things out week by week. He recalls missing the era when albums dropped with no advance teasing, citing Turnpike Troubadour's Price of Admission release, promoted only with a desert billboard, as a bold move he admires even though it might not be algorithmically optimal, and acknowledges the tension between authenticity and paying the bills.
Live performance of Clothesline 1:25:31
Dylan performs the song Clothesline live, a track about heartbreak and being left behind, using the image of hanging on a clothesline to describe feeling discarded by someone who changed their mind. The episode closes with thanks between host and guest, an announcement that Dylan's new album releases September 25th, and a reminder from the host to check that the subscribe button is actually pressed.
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