In this episode of Modern Wisdom, Chris Williamson speaks with musician Dylan Gossett about his unexpected rise to success with the viral song "Cole" and the challenges of maintaining artistic authenticity in the modern music industry. Gossett shares how he wrote and recorded the song in 25 minutes during a difficult period, initially posting it with minimal engagement before it eventually transformed his career. He discusses his conscious rejection of conventional social media tactics and industry promotional formulas, preferring to focus on live performances and genuine fan connections over chasing viral moments.
The conversation explores broader tensions between art and commerce, including how technology and AI impact creativity, the role of algorithms in shaping music trends, and the economics of modern touring. Gossett and Williamson also examine why country music provides an emotional outlet for male vulnerability, and how artists navigate the pressure to replicate success while staying true to their creative vision. The episode offers perspective on balancing artistic integrity with the practical demands of building a sustainable music career.

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Dylan Gossett writes "Cole" in about 25 minutes while enduring grueling days working event operations at Circuit of the Americas racetrack in Austin. He records the song on his laptop with minimal production, sitting on his bed with his guitar. The song emerges from a place of struggle, capturing the feeling of relentless effort without visible rewards—a sentiment that resonates deeply with listeners who relate to working hard while still feeling stuck or unsuccessful.
Gossett's wife Julia immediately recognizes the song's potential and encourages him to share it widely. A camping trip with friend Kayden becomes the turning point when Kayden insists the song deserves an audience. Despite initial reluctance toward social media, Dylan posts early versions of "Cole" on TikTok with minimal engagement. He sits on the song for over a year until "to Be Free" gains traction, prompting him to try again—this time, a video post "changes everything."
The viral success of "Cole" transforms Dylan's life dramatically. The transition from event operations to touring and industry logistics proves jarring, though he maintains perspective, recognizing that everyday headaches like replacing a guitar tech are problems he once dreamed of having. The breakthrough comes shortly after he marries Julia and settles into a new home, providing stability amid sudden fame. Dylan realizes he doesn't need to chase viral moments to sustain his career, choosing to focus on ticket sales and live performances over fleeting social media trends.
Dylan consciously avoids conventional social media tactics in crafting "Cole," intentionally delaying the main hook until the second chorus to prioritize strong songwriting over viral 15-second snippets. He strictly limits promotional posts to seven to ten times—far fewer than typical industry standards—rejecting ads and repeated content drops. For Dylan, the success of "Cole" remains wonderfully unpredictable, leaving him uncertain whether tiny factors like mood, weather, or video choice made the difference between viral phenomenon and obscurity.
Dylan's career illustrates the persistent tension between genuine creativity and industry expectations. He rejects traditional promotional formulas like tightly planned releases and constant advertising, frustrating his team but upholding artistic standards. Dylan describes a shift from creating music for passion to facing pressure to meet industry timelines and strategic calendars, though he remains aware of why formulaic approaches work commercially, even as he resists them.
Dylan discusses "audience capture"—a phenomenon where creators gradually drift into giving audiences what they expect rather than what the artist genuinely wants to create. He experiences this tension directly when fans demand stripped-down "porch versions" over produced studio tracks, making him feel boxed in as the "acoustic guy" despite wanting to evolve his sound. The industry rewards consistency, so artists often lean into proven formulas even when personal growth pulls them elsewhere.
To maintain authentic creativity, Dylan has deleted much of his social media presence and unfollowed industry accounts, finding the barrage of ads and criticism overwhelming and destructive. He works to separate his creative process from metrics and industry trends, preferring to write on his couch at home with his wife Julia watching TV—using her real-time feedback as his sounding board—rather than in professional Nashville writing rooms where music is produced as part of an industry assembly line.
Gossett values how technology democratizes music creation, allowing him to write and record "Cole" independently on his laptop. Yet he voices deep concern over AI-assisted production leading to formulaic outcomes, where the industry's hunger for replication strips original art of its uniqueness. The ethical boundary between modest technological tools and AI-generated content remains murky. Gossett distinguishes between opening a rhyming website for writer's block versus using AI to pen lyrics or melodies, arguing the latter diminishes creative ownership: "You're either making music, or something else is making the music for you."
Gossett draws parallels between music production's evolution and larger societal patterns favoring convenience over effort. He recalls when musicians recorded live with tape, where imperfections became part of a song's unique tapestry. Modern technology enables endless editing and perfecting, but can sterilize the art. He observes how culture has shifted toward instant gratification—Uber Eats, YouTube Shorts, watching content at 2x speed—eroding what makes achievement meaningful. Chris Williamson echoes this by citing Mark Manson: "Easy wins are forgettable, hard ones change you."
A new paradox arises as the industry learns to engineer and commodify imperfection itself. Gossett notes that the quest to appear "authentic" has become performative, with producers deliberately manufacturing sonic imperfections—"artificially natural"—to create "fake rawness." While he values honest imperfections born from circumstance, not design, he worries the industry continues marketing lo-fi aesthetics as proof of authenticity, undermining genuine realness.
Dylan describes the prevalence of "truck edits," where marketing teams create moody video clips with trucks and song lyrics to boost appeal through dedicated Instagram ecosystems. As an industry insider, he easily spots when a song's trajectory is artificially elevated by coordinated campaigns rather than organic success. Williamson notes that "the escalation of firepower" in marketing raises the entry bar for artists seeking recognition. Unlike those riding algorithmic waves, Dylan focuses on organic growth through ticket sales and genuine show attendance.
Williamson explains "Blue Dot Fever": many popular artists now struggle to sell enough tickets to sustain tours, partly because skyrocketing ticket prices and dynamic pricing make concerts inaccessible. Gossett notes that even in the worst seats, expenses reach four figures after factoring in hotels, parking, and merchandise. Emerging artists offering affordable intimate shows compete with established acts' premium arena shows, forcing audiences to choose between one expensive event or multiple cheaper alternatives. This tension impacts agents, promoters, and artists as cost-of-living pressures restrict what audiences can actually afford.
Music saturation and increased touring competition challenge artist breakthroughs. Williamson cites data showing rap music dropped from 34% of Billboard's Top 10 in 2020 to 17% by 2023, while country climbed from 7% to 27%. Gossett sees such swings as cyclical but questions whether trends reflect authentic preference or marketing influence. Despite preferring organic creativity, Dylan acknowledges the necessity of strategic planning for career sustainability, though he expresses nostalgia for when artists could drop complete albums as surprises. He admires approaches like Turnpike's mysterious desert billboard strategy, valuing surprise and artistic control over algorithmic reach.
Gossett observes that at country shows, men often stand arms around each other, passionately singing lyrics together—yet would never openly discuss their feelings with friends in daily conversation. Williamson suggests this reflects broader masculinity issues, where men are comfortable seeing emotions echoed in songs but struggle to expose them directly. Gossett likens the experience to group therapy, explaining that music offers many men the only space where vulnerability feels acceptable. Williamson notes that music frames vulnerability artistically, providing emotional distance that allows men to engage feelings safely.
Gossett observes a gender divide in how emotional disclosure is received: when women sing about vulnerability, many male listeners are dismissive, but when male artists voice vulnerability, audiences respond with empathy and support. Williamson and Gossett agree this pattern reflects cultural narratives where female country emphasizes empowerment while male songs foreground vulnerability, legitimizing masculine emotion within socially accepted frameworks.
Gossett finds that writing sad, emotionally complex songs flows more naturally than happy ones, which can sound cheesy or superficial. Williamson comments on the artistic pressure to maintain struggle or friction, observing that as a songwriter's life improves, the natural wellspring of material from lived emotional struggle can dry up. Gossett celebrates country music's storytelling tradition, which allows him to invent characters and explore emotional complexity without requiring ongoing personal crisis for material. He cites his song "Lone Old Cowboy" and Dolly Parton's "Jolene" as examples of how narrative blending achieves deep emotional resonance while using invention and distance to grapple with complex feelings.
1-Page Summary
Dylan Gossett writes "Cole" in about 25 minutes, one of the fastest songs he's ever finished. The inspiration comes during a tough period while living in Austin, working long, grueling days in event operations at the Circuit of the Americas racetrack—often residing in a trailer on-site in the Texas heat. Gossett describes the songwriting process as organic and deeply personal, sitting on his bed with his guitar and laptop, recording with minimal equipment. At the time, he's writing songs solely for passion and as an outlet, without any particular expectations or ambition for recognition.
"Cole" emerges from a place of struggle, mirroring the feeling of relentless effort without visible rewards. Gossett recalls a trying but not overwhelming period in his life—enduring everyday challenges, feeling stuck, and not seeing immediate progress despite hard work and happiness at home with his wife and dog. This sentiment echoes in the response from listeners, with top comments reflecting feelings of working hard on oneself while still feeling lonely or unsuccessful.
After finishing "Cole," Gossett’s wife Julia immediately sees its potential, enthusiastically sharing it via Snapchat and with friends—revealing Dylan’s hidden singing talent to their social circle. Despite Julia’s encouragement, Dylan initially holds back from social media or wider release, uninterested in TikTok and skeptical of the digital self-promotion grind.
The turning point comes on a camping trip with friend Kayden and their spouses. Kayden—who Dylan describes as having the best ear of anyone he knows—pushes him to play "Cole" again, records a voice memo, and insists the song deserves an audience. Spurred further by Julia, Dylan reluctantly tries posting on TikTok, despite his dislike of such platforms. Early TikTok videos of "Cole" meet little initial interest, and Dylan sets the song aside for a while.
Dylan sits on "Cole" for a year or two, not actively posting on social media. Even when he does share, the videos generate minimal attention. It isn’t until after his first song, "to Be Free," starts gaining traction that he decides to try again with "Cole"—this time, a video post “changes everything.” The original release is truly lo-fi, engineered and mixed at home (except for mastering), and Dylan now even considers today's released version rough, like a demo. The song needed remastering after its first release as it didn’t sonically match other songs.
The viral success of "Cole" brings massive change. Dylan describes the transition from event operations to a career in music as "jarring." Suddenly, he's attending to industry logistics, touring, and managing production tasks that were previously unimaginable. He reflects that everyday headaches—like replacing a guitar tech—are the very sorts of problems he once dreamed of having, and he tries to maintain perspective in the whirlwind.
The timing of "Cole’s" breakthrough is significant. It comes shortly after Dylan marries Julia and the couple settles into a new house, providing stability just as his world changes with sudden fame.
As Dylan navigates new industry demands, he realizes that he doesn't need to chase viral moments to build his career. He chooses to focus on ticket sales and live performances, prioritizing stable, long-term success over fleeting social media trends. ...
Dylan's Journey: From "Cole" to Success Manager
Dylan Gossett’s career illustrates the persistent tension artists face as they attempt to balance genuine creativity against industry expectations and commercial pressures. As his professional profile grows, so do the challenges that come with maintaining authenticity.
Dylan expresses his reluctance to strictly follow the conventional industry formulas for success, such as tightly planned single releases and constant music promotion. He prefers a more organic, week-by-week approach and is hesitant about the “system formula thing.” Dylan notes frustration among his team over his resistance to ads and constant promotional efforts, but he prioritizes artistic integrity and staying true to his process, even if this potentially reduces his commercial impact.
Dylan describes a shift from the passion of creating music for himself to facing pressure to meet industry standards and timelines. The excitement of releasing new music is now intertwined with strategic calendar planning and considering what songs to tease or crowdsource, reflecting a necessary but sometimes uncomfortable adaptation as his profile rises.
While Dylan resists fully adopting the industry’s formulaic strategies, he acknowledges why some methods—like using social media for promotion or carefully selecting singles—make sense for music’s commercial success. He’s aware that these approaches work to boost visibility but consciously chooses not to lean entirely on them.
Dylan discusses “audience capture,” a phenomenon described by Chris Williamson, where creators gradually drift into giving audiences what they expect rather than what the artist genuinely wants to create. This cycle can lead to repeated formulas, with artists feeling compelled to stick to a style or persona that brought them initial attention, sacrificing evolution for the security of audience approval.
Dylan shares his struggle with this dynamic: when he releases upbeat, produced studio versions of his songs, fans often demand the stripped-down “porch version.” This feedback can be limiting, making him feel boxed in as the “acoustic guy.” He wants to expand his sound, inspired by artists like Billy Joel and Bob Dylan, who weren’t afraid to evolve, yet he also feels the weight of audience preference.
Dylan observes that the industry favors consistent, easily marketable identities, rewarding musicians who capitalize on their niche—even if it comes at the expense of creative growth. He knows many artists who would like to pursue different musical styles but fear poorer commercial performance if they stray from what’s already successful.
Dylan has deleted much of his social media presence and unfollowed most country music industry accounts, finding the barrage of ads, promotions, and criticism exhausting and detrimental to his creative process. He contrasts the original intent of ...
Authenticity vs. Commerce: Balancing Art and Business Pressure
Dylan Gossett openly values the democratization of music technology, emphasizing its positive impact on accessibility. He praises how technology allows him to write and record a song like "Cole" on his laptop and release it independently, with the freedom to bypass traditional gatekeepers. This empowerment, he notes, is an “awesome” development that fosters creativity for individuals who once needed industry backing.
Yet, Gossett also voices deep concern over AI-assisted production leading to formulaic outcomes. He worries the industry’s hunger for replication and commodification—"How do we replicate it? How do we dump a truckload of money behind it?"—quickly strips original human art of its uniqueness, pushing it toward mass production where genuine inspiration is mined and replicated by machines.
The ethical boundary between using modest technological tools and allowing AI to generate substantial portions of a song remains murky for Gossett. He draws a distinction between opening a rhyming website to solve writer’s block and using AI to pen lyrics or melodies. The former, he argues, is an extension of human intent, while the latter risks diminishing creative ownership: "You're either making music, or something else is making the music for you." He confesses, "I don’t think I have that thing in me where I’m like, how much can I squeeze out of this with AI to help me write this song without people thinking that it’s AI?"
Gossett recognizes a spectrum of AI use in music. AI-powered assistance for producers and engineers, such as help with audio engineering or EQ adjustments, seems less problematic than AI-generated song structures or lyrics, which threaten to overshadow the genuine, imperfect process at art’s heart. Wherever the line sits, he contends, is ultimately defined by an individual's own moral compass: "The only place that you can make this decision is my own kind of moral gauge for what I want on the other side of it."
Gossett draws parallels between the evolution of music production and larger societal patterns favoring convenience over effort. He recalls a time when musicians recorded live in studios with tape; imperfections from those sessions, such as a hat falling on piano keys, became part of a song’s tapestry, making the performance unique and sometimes magically perfect in its flaws. Modern technology enables musicians to edit, correct, and perfect endlessly, but it can sterilize the art, erasing the “key hit” that gives a record life.
He observes how culture has shifted from real-time execution (sit-down restaurants, movies) to revision and instant gratification (Uber Eats, YouTube Shorts, watching Instagram Reels at 2x speed). Gossett admits to experiencing these patterns himself—doomscrolling on tour, letting his phone summarize messages, and feeling his mind disengage from genuine effort: "I’m getting dumber by the day... I’m not exercising my mind." He yearns for the growth and satisfaction that comes from genuine struggle, relating it to why mere participation trophies in childhood feel empty compared to true earned victories.
Chris Williamson echoes this by citing Mark Manson: “Easy wins are forgettable, hard ones change you.” Together, they worry that the AI-driven pursuit of easy wins may erode what makes achievement meaningful. Despite the appeal of convenience, Gossett insists that art—like life—gains value from hard work, persistence, and personal investment, while AI-assisted shortcuts threaten that meaning: "There’s no like highs and lows in that... you’re just very—yeah, I don’t know."
Tech & Ai In Music: Ethics and Convenience Costs
The contemporary music industry has become a battleground of aggressive marketing, saturated touring schedules, and rapidly changing audience preferences, challenging artists to navigate authenticity, business acumen, and algorithmic influence.
Dylan Gossett describes the prevalence of "truck edits," where marketing teams create moody video clips featuring trucks and overlay song lyrics to boost a track’s appeal. These videos, thriving within dedicated Instagram ecosystems, are designed to catch music listeners who follow such content for song discovery. Teams will intentionally pump a song through these visually-appealing edits, leveraging the popularity of truck and similar lifestyle accounts for targeted marketing.
Gossett, as an industry insider, can easily spot when a song’s trajectory is being artificially elevated by marketing machinery. He notes the clear markers of a coordinated campaign: trending audio clips, an abundance of video edits, and predictable pushes that signal involvement of a well-resourced team. Chris Williamson adds that "the escalation of firepower" in marketing raises the entry bar for artists trying to achieve even modest recognition, as many moderately successful songs now have entire teams orchestrating their visibility.
Unlike those riding algorithmic waves or viral trends, Gossett aims for organic growth, focusing on ticket sales and genuine show attendance. Aside from one early viral moment, his career relies on building an audience by putting people in seats, not through artificially manufactured moments. He views continued growth of live shows as the truest measure of success, recognizing that standing out has become far more complicated as music marketing saturates every platform.
Chris Williamson explains "Blue Dot Fever": many popular artists—even those headlining stadiums or arenas—now struggle to sell enough tickets to keep tours afloat or avoid cancellations, in part because of skyrocketing ticket prices and dynamic pricing strategies implemented by major sellers like Ticketmaster and Live Nation. Gossett notes that for him and his wife, even sitting in the worst seats yields a four-figure expense after factoring in tickets, hotels, parking, merchandise, and childcare. This steep cost deters many fans from attending large shows.
Gossett points out the competitive tension: emerging artists offer smaller, intimate performances at affordable prices (e.g., $15 per ticket), while established acts price most fans out. With so many acts touring simultaneously, audiences are forced to choose between splurging on one premium event or attending several smaller ones.
As audiences crave real-world events and live connections post-pandemic—including concertgoing and other cultural gatherings—cost-of-living pressures restrict what they can actually afford. Williamson emphasizes how everyone is optimistic about the live event market, but venue owners, promoters, and artists alike face the dilemma of maximizing profits without pushing fans away. Gossett adds that agents find it increasingly hard to predict growth, as once-reliable metrics like previous sellouts and city-by-city returns now face audience hesitation: fans opt to try a new artist’s affordable show over returning to see a familiar act due to limited discretionary income.
The influx of touring acts means new artists, often discovered through platforms like TikTok, play small-capacity venues at attainable pricing, while established stars keep pushing ticket prices higher. This crowding causes competition not just for attention but for limited audience spending.
Gossett’s own approach—building his tour’s reputation through sales rather than virality—faces mounting challenges as economic pressures force fans to make hard choices and as more artists fight for both venues and consumer dollars. Agents, promoters, and musicians must recalibrate their expectations in a rapidly shifti ...
Modern Music Industry: Marketing, Touring, and Algorithm Dependency
Dylan Gossett and Chris Williamson discuss how country music serves as a crucial space for male emotional expression, providing an outlet that is often unavailable in daily life due to expectations of stoic masculinity.
At country music shows, Gossett observes that men are often at the heart of the crowd, arms around each other, passionately singing lyrics together. He notes that while these men would never talk openly about their feelings with friends or in group chats, in the context of the music, they experience a cathartic release. Williamson suggests this dynamic reflects broader issues with masculinity, where men are comfortable seeing their emotions echoed in songs but struggle to expose them in direct conversation.
Gossett likens the experience to group therapy. He explains that, for many men, music offers the only space where vulnerability feels acceptable. In social settings outside music, expressing feelings might draw mockery or disapproval, but when wrapped in country melodies, songs that articulate these emotions become powerful connection points. Gossett shares that many male fans relate deeply to such songs, even if they would never admit it aloud, letting country music serve as a surrogate for emotional dialogue.
Williamson points out that music frames male vulnerability artistically, providing emotional distance that allows men to engage feelings safely. This group setting, mediated by live performance and shared lyrics, offers a form of communal therapy, reinforcing that, while direct vulnerability remains challenging, artistic expression creates socially acceptable pathways for men to process their inner lives.
Gossett observes a notable gender divide in how emotional disclosure is received within the genre. When women sing about vulnerability—particularly around relationship struggles—many male listeners are dismissive, regarding such themes as stereotypical or tiresome. In contrast, when male artists voice vulnerability, the same audience responds with empathy and support, celebrating the expression as powerful and relatable.
Williamson and Gossett agree that this pattern reflects cultural narratives where female country songs tend to emphasize empowerment, while male songs foreground vulnerability. The music provides men with an opportunity for emotional complexity within a framework that is socially accepted as masculine. This distinction helps explain country music’s strong resonance among male audiences, as it legitimizes masculine emotion and provides space for connection rarely found elsewhere.
Gossett finds that writing sad, emotionally complex songs often feels more natural and resonant than writing happy ones, which can sound cheesy or superficial. He notes that heartfelt, melancholic songwriting flows more easily, enabling him to paint powerful images and tap into emotional depth. Although he enjoys writing songs about love, particularly about his wife, he finds generic happy songs more challenging to craft authentically.
Williamson comments on the artistic pressure to maintain a sense of struggle or friction, observing that many successful artists' most powerful work stems from periods of difficulty. As a songwriter’s pe ...
Male Vulnerability in Country Music: An Emotional Outlet
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