How To Make Your Creativity Beat The Algorithm - Dylan Gossett (Live Performance)
In a Nutshell
Dylan Gossett reveals how his song "Cole" succeeded by resisting algorithmic optimization—posting it only 7-10 times instead of the industry standard 50, avoiding 15-second dance clips, and refusing to run ads. He explains that maintaining authenticity becomes harder as success pulls artists away from the real-world experiences that fuel their best work, creating a "well-spring problem" where touring and industry life replaces the struggles that originally made them great. The conversation highlights how both music creation and audience connection are increasingly threatened by commercialization of authenticity, AI-generated content, and the pressure to engineer "raw" or "natural" results.
These notes were generated by AI and may contain inaccuracies.
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Dylan Gossett performs "Cole" live. The song was written in approximately 25 minutes, one of the fastest compositions he's created. It began with the hook line "pressure makes diamonds" which he recognized as strong material to build around.
Gossett wrote the song on his phone while sitting on a dog kennel in his apartment. At the time, none of his friends knew he could sing. After writing it, he showed the song to his wife Julia who immediately recognized its quality and shared Snapchat videos with friends, revealing his musical talent.
The song sat unreleased for approximately one to two years. During a camping trip with friends Kaden and MK, Kaden - who has exceptional musical instincts despite not working in A&R - heard the song, voice memoed it, and insisted Gossett do something with it. His wife encouraged him to post on TikTok despite his initial reluctance.
At the time of writing "Cole," Gossett was working at the Circuit of the Americas racetrack in Austin, Texas in event operations. He had started as an intern and lived in a trailer on his parents' RV at the job site for months. The song emerged during a difficult period involving intense work demands during F1 season and general life struggles, though he clarifies he wasn't in the worst place of his life.
The top YouTube comment on "Cole" (with 22 million plays) states the song captures the feeling of working on yourself and making progress while still feeling lonely and like a failure. Gossett relates to this, describing the sensation of putting in hours without feeling any different or seeing rewards.
He notes that without going through his previous job and real-world relationship experiences outside of college, he wouldn't have the frame of reference needed for his current music career success.
Gossett emphasizes that music is fundamentally a business, contrary to the romantic notion of simply strumming a guitar and collecting money. He often feels more like a business manager than an artist.
He references the book "The E-Myth Revisited" by Michael Gerber, which tells the story of a woman who loves making cakes, opens a bakery, and eventually stops making cakes entirely due to business demands. This illustrates how success in any creative field requires learning to say no to opportunities and protecting the time that originally made you great.
Gossett discusses how expectations and problems change with success. Goals that once seemed desirable (like having a guitar tech) become new sources of stress when that person needs replacing. He mentions the concept of the hedonic treadmill applying not just to possessions but to goals and problems themselves.
Gossett posted "Cole" only 7-10 times total, with four posts around its initial release. He deliberately avoided the industry standard of posting a song 50 times, pre-save campaigns, and extended promotional periods. He hated how music promotion focused on 15-second clips optimized for dancing and reposting rather than showcasing actual songwriting quality.
The song's strength lies in its writing, particularly lines like "I've seen heaven without dying, made the devil without trying" which he was proud of and wanted listeners to discover as a payoff rather than leading with the chorus.
Gossett obsesses over maintaining authenticity and has lines he won't cross. He initially refused to run ads despite pressure from his team. He recognizes that authenticity becomes difficult to maintain once teams recognize its commercial value, as people begin performing authenticity rather than being authentic.
Billboard data shows rap music's share of the top 10 decreased from 34% (2020-2023) to 17% (2025-2026), while country music increased from 7% to 27% during the same periods. Gossett notes that success tends to occur at the extremes - either highly polished productions or very raw, stripped-back content - while the middle ground struggles.
Gossett can identify when songs have marketing teams behind them by looking at audio patterns and seeing coordinated promotion across ecosystems like truck edit accounts on Instagram. However, even with extensive marketing support, songs still need genuine quality to succeed rather than just sounding derivative.
He notes that breaking through has become significantly harder as moderately good songs now have armies of clippers, truck edits, and boat edits promoting them.
Blue dot fever refers to a wave of artists, many of whom are pretty big, doing large venues including stadiums and arenas but not selling out or often not selling enough to continue with the show or killing the tour entirely. Part of it involves artists questioning their own relevance, while another huge factor is ticket prices and how much people are getting squeezed through dynamic pricing by Ticketmaster and Live Nation.
The live music market shows conflicting forces: everyone is bullish on live music, comedy, and real world events with people seeking phone-free experiences and trying to touch grass, yet cost of living pressures mean people have less disposable income. Venues must balance squeezing ticket prices without squeezing too much. A stadium show can become a four-figure day including hotel, parking, merchandise, and babysitter costs, even for bad seats.
When a TikTok artist is playing down the road for a $15 ticket with 200 people going, audiences increasingly choose the smaller, more affordable option over expensive stadium shows. This creates challenges for agents who traditionally built touring off sellouts and returning to cities to do 20% more tickets after successful albums.
Overnight success used to be an insult but now feels like what everyone's chasing. Dylan wasn't ready for rapid success but it happened at a perfect moment after getting married and settling into a house. The hardest part is maintaining success, as many artists have a big moment where everyone knows their song, then within a year cannot sell shows because they only had that one pushed song.
Dylan has deleted much social media and unfollowed country accounts because exposure feels overwhelming. The sensation isn't anxiety or stress but rather a need to have a life outside the industry. Instagram has shifted from seeing what friends post to constant ads and promotion. People reviewing country artists while hiding behind screens creates a weird dynamic, and he tries to separate his life from his work.
As artists become successful, their ability to do the things that made them successful becomes harder to access. For art to imitate life, you have to live a life. Comedians who get bigger find their acts increasingly about airports, dinners, shows, and hotels because that's all they know. When you're a big touring act playing multiple shows every weekend, your friends are also in the industry, and you lose the wellspring you're drawing from.
Marketers and branding professionals face the same challenge - if all you're consuming is derivative work of other people talking about the same thing, where do you draw new inspiration? Dylan wants to remain the person he would market to, wanting to create music that the earlier version of himself would love as a fan.
Miley Cyrus requires certain time off the road to just live and experience life outside of touring. This connects to the broader need to get back to where you started as success pulls you further away.
Dylan's process typically starts on the couch with his wife watching TV. He sings gibberish to find melodies, eventually words come to him that feel thought-provoking. For the song "Headed Back to Austin," he knew where he wanted to go but didn't have anything, starting with 30 minutes of noodling rather than trying to write a song. The process involves forming consonants and vowels until they become words.
Nashville's collaborative writing engine is very different from Dylan's couch-based approach. He has nothing against those writers who are incredibly talented, but he cannot work that way. His closest collaboration is writing with his brother Blake or multi-instrumentalist Colton, though even then it's different from his preferred solo process.
Dylan's brother Blake wrote "Rambling," the title track of the album, which Dylan considers one of the best songs. Dylan only wrote the chorus and a little melody for the chorus. The song features fingerpicking guitar work that Dylan cannot replicate, and Blake is a significantly better guitar player.
Dylan is open to collaboration and no longer believes every word must be his own. Writing is his passion almost more than singing, and he's particular about what songs say and sound like. He thinks he could write for someone else, but not a song he would want to sing himself because he would want to sing it.
John Bellion took five years off from producing and publishing music after a public altercation with his label. He focused on making music for other artists and creating banger after banger. When asked how he knew he wanted to return to making music, he explained that when reviewing demo tracks for other artists, he would find himself double-tapping certain tracks and thinking "that one's for me," hearing a bit of selfishness or ownership coming back.
Comedy writers do versions of ghost writing, and every major roast online involves armies of writers contributing material. Comedians now credit writers in Instagram captions when posting clips. Shane Gillis at the ESPYs gave a line and explicitly stated it wasn't his, calling out the meta of the writing process. Less than 10% of touring comedians write their entire sets themselves.
Dylan takes pride in his words and tries to maintain ownership of his creative output. When he has a chorus and verse and needs only a bridge, he often resists help because he wants to complete his own thought. He has never been offered an amazing song to sing except for his brother's "Rambling," which was an obvious choice for the album.
A friend bumped into an ex and became regretful about ending the relationship, despite having been certain at the time. The fading affect bias explains that bad memories fade with time but good ones tend not to, creating a psychological immune system. However, a side effect is that as you get older, you assume wisdom compounds with age, when in matters of emotion you're simply further from the evidence.
When facing a 2,000-word writing project that needed to be 500 words, the option existed to put it into ChatGPT for deep research to create flow and structure. However, choosing not to use AI meant the idea wouldn't be concretized by external processing, and the writer would always know they didn't put the finishing garnish on the dish themselves.
There's a yearning to work your mind rather than have technology do it. On tour, autopilot mode and doom scrolling create the sensation of getting dumber daily without exercising the mind. The accomplishment of earning something through effort provides a feeling that participation trophies cannot match.
Mark Manson's line captures the core issue: "Do hard shit not because it's fun, but because the win actually means something. You bled for it. You broke for it. You earned it. Easy wins are forgettable. Hard ones change you. That's the point." This applies to AI choices in small ways, like whether to write a thank you letter yourself or have AI generate it, because people care about the effort behind the gesture.
People care about the effort involved in writing a card by hand rather than the physical card itself. Moon Pig and Magpie card services allow users to type messages that get printed and shipped, but receiving a handwritten card is at least twice as nice as something printed off the internet. The value isn't in the 299 piece of paper received in the mail, but in the demonstration of love from afar that someone couldn't otherwise show.
AI has its place in certain parts of the world as a technological advance, similar to how people no longer handwash clothes and hang them on clotheslines outside. However, a clear line exists when it comes to artistic or sentimental matters. The whole point of art is that it's not perfect and feels like something only humans can do. With sentimental expressions like writing letters, the purpose is to have an emotional effect on the recipient, not just to check a box by having ChatGPT generate the content.
The decision to do the harder thing versus the easier thing will encroach into every area of life. This includes whether someone wants to one-click order flowers to their partner's door because she's having a hard day, or drive to the florist, pick them up, and hand deliver them. There is an explicit, real-world, tangible difference between these two approaches.
Convenience is expanding across all aspects of life. What started as sit-down restaurants became drive-thrus and now Uber Eats. Movies became YouTube and now YouTube Shorts. This pattern keeps expanding and becoming more distilled.
People find themselves speeding through Instagram reels at 2x speed, essentially trying to speed themselves with the algorithm. While this might be acceptable during bathroom breaks when wanting to get to the point, it starts creeping into everything. Twenty years down the road, musicians might face situations where they need to pay bills and write new songs but lack inspiration, leading to questions about what stops people from using AI to generate sellable content.
Modern recording allows musicians to go into studios and pluck songs together, chopping perfect takes. Fifty years ago, recording happened in a single room on tape, requiring real-time decisions about whether to run out of tape or continue. Engineers used Xacto knives to physically splice tape together. This constraint meant that on old records like Elton John albums, you can hear imperfections like a hat falling on the keys, but they kept the take because it was great.
Imperfections give records life, but as soon as imperfections are recognized as giving something life, they begin to be engineered. The authenticity and stripped-back quality become marketable commodities.
Some producers want things to be natural so badly that they engineer naturalness, creating artificially natural results. This represents a commodification of everything, where less gatekeeping by technology or expertise tempts more people to create content. The question becomes whether we can remove drudgery from people's lives without taking away the things that actually matter to them.
Music has historically involved fluidity with teams of writers and band members who may leave or pass away, yet songs continue to be performed. Technology has democratized music creation, allowing anyone to write songs on laptops and release them without traditional gatekeepers. This access enables independent artists to compete with money-pushed, multi-songwriter productions.
However, this democratization creates a slippery slope. Once people see what works, they seek ways to replicate success, potentially using AI to generate lyrics or master tracks. The question becomes where to draw the line: if AI helps craft lyrics that someone then sings, is it still their song? The decision ultimately comes down to individual moral gauges and gut feelings about whether someone is making music or having something else make music for them.
Songwriting approach depends on the mood of the song itself. Sad, heartfelt songs can be easier to write and paint clearer pictures than happy songs, which can come off as cheesier. Love songs about partners can be written well and become favorites, but straight-up happy bar songs prove more difficult to write.
Male sadness dominates modern country music partly because it's one of the few places where men feel allowed to talk about emotions without being told to get it together. Country music serves as a form of dude therapy session where blue-collar men who wouldn't normally discuss feelings can connect deeply through lyrics. At shows, the people singing most passionately are often men with their arms around each other who would never discuss these feelings outside the concert setting.
This creates an interesting dynamic where men feel comfortable seeing emotions reflected in lyrics but remain uncomfortable exposing them in daily life. Music provides a defense mechanism that frames vulnerability in an artistic, romantic way, creating distance while still allowing expression.
Female country songs tend to be more empowering, while male songs focus on vulnerability. When women sing about vulnerability, male audiences may dismiss it as another breakup song, but when men do it, there's a sense of connection and understanding. Music becomes the male outlet for emotional expression in ways that daily life doesn't permit.
Happy music proves the hardest to write, not because happiness can't be expressed, but because it doesn't come as naturally as sadder, more heartfelt content. While love songs about partners flow easily, straight-up celebratory bar songs remain challenging to compose effectively.
When life is going well, creating authentic art becomes more difficult. Artists may need to imagine scenarios they haven't experienced or draw from stories heard from others. People resonate strongly with pain and vulnerability in art, which creates a challenge when an artist's personal life lacks hardship.
Songwriters can create compelling fictional stories rather than relying solely on personal experience. Dylan has a song called "Lonal Cowboy" about a man who gets cheated on, kills the person involved, and goes on the run - a story he never lived. This approach draws from traditional western music traditions like Marty Robbins' gunfighter ballads, which function like modern fables or mythology.
Dolly Parton's "Jolene" originated from two separate sources. The story came from a tall redheaded bank teller who flirted with Dolly's husband Carl shortly after their marriage. Carl enjoyed the attention, and Dolly joked he seemed to spend excessive time at the bank despite having little money. The name "Jolene" came from a different source - an 8-year-old redheaded fan who asked Dolly for an autograph. Dolly thought the name was beautiful and told the girl she would use it.
Whitney Houston's version of "I Will Always Love You" spent 14 consecutive weeks at number one and became one of the best-selling singles of all time. This record was recently broken by Ella with 15 consecutive weeks. Dolly Parton wrote both "Jolene" and "I Will Always Love You" on the same day, demonstrating extraordinary creative output.
Artists face pressure to maintain their established sound versus evolving their music. When Dylan plays acoustic versions of songs on his back porch, audiences often request that the studio versions remain similarly stripped down. However, he believes artists need to expand their sound and avoid getting trapped in their own tropes. Billy Joel and Bob Dylan both made deliberate efforts to change their sound throughout their careers.
Audience capture occurs when creators gradually shift their content to match what they believe audiences want, rather than creating from authentic impulse. This process starts with testing different content, finding what resonates, and then amplifying those elements until creators become caricatures of their audience's preferences. The result is creators resenting their audiences for forcing them into shapes that don't reflect their authentic selves.
Criticism capture represents the opposite of audience capture - creators behave to avoid criticism rather than encourage desire. This manifests as excessive caveats, disclaimers, or aggressive preemptive stances designed to deflect potential criticism before it occurs.
Modern social media creates unprecedented instant feedback loops for artists. Walking off stage directly into social media commentary can significantly impact creative decisions and mental wellbeing.
There's a notable difference in production standards between male and female artists in live performances. Morgan Wallen's stadium shows contrast sharply with the highly choreographed, theatrical productions like Tate McCrae's performances involving liquid gold elements. This represents a shift from earlier eras when both male and female acts had more similar production approaches.
There's an ongoing tension between business-driven pre-release strategies and preserving the mystery of new music. Traditional album releases allowed listeners to discover songs without prior exposure. Modern marketing involves teasing multiple tracks in advance, which can diminish the excitement of a complete album drop. Turnpike Troubadours exemplified an alternative approach by releasing no singles for "Price of Admission," instead using only a billboard announcement two weeks before release.
Dylan performs his song "Clothesline," which he believes could be a single from his upcoming album. The performance demonstrates his preference for feeling out release decisions rather than following predetermined formulas and schedules.
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