Some songs take the long way home. Jeff Middleton joins us to map that winding route—Jersey kid to Nashville lifer—through a Warner deal with The Dirt Drifters, a thousand-dollar RV that literally went up in flames, and the four-year journey of Drowns The Whiskey from a bus write to a multi-week No. 1 with Jason Aldean and Miranda Lambert. It’s a story of grit, timing, and how a better demo can change fate.

We dig into the changing economics of songwriting—how streaming thinned the middle class that once survived on album cuts—and what it takes to keep going when the money and momentum don’t line up. Jeff shares how co-writing became a learned craft, why he now “lets the room be the room,” and how switching from road mode to writer mode saved his best work. He also pulls back the curtain on American Knights, co-written with Austin Jenckes and Mike Walker, and the unusual path that gave the song multiple lives with Morgan Wallen and Lee Brice.

Then there’s AI. Jeff doesn’t flinch from it—he uses Suno for fast, pitch-ready demos and even built Song Script AI to help writers with better prompts. But he’s clear-eyed about the line: algorithms look backward; great songs reach forward. The job is still to move people, to write from the heart, and to make music that feels undeniably human. If you’re an aspiring songwriter, you’ll get field-tested advice, sharp reality checks, and a reminder that authenticity isn’t a brand; it’s the work.

If this conversation hit a nerve, follow the show, share it with a friend who writes, and leave a quick review so more people can find these stories. Your support helps us keep bringing songwriters and their hard-won lessons to the mic.

What if the song that changes your life starts with a brief, a laugh, and a note you weren’t sure you could sing? We sit down with songwriter Abram Dean and trace the unlikely trail from church costumes and a middle-school talent win to LA’s genre-blend grind, a Warner publishing deal, and a move to Nashville that felt less like strategy and more like calling.

We unpack the room where “Gonna Love You” took shape for Parmalee—a “power ballad” request that turned into a simple, soaring promise, a months-long hunt for the right bridge, and a cut day that proved how the right voice can unlock a song. Abram shares how that track later became a conduit for the band to tell a painful family story, showing how country songs carry more than romance—they hold resilience. Then we pivot to “Devil Don’t Go There,” where a stubborn idea flipped POV, landed with Laney Wilson, and raced from Friday write to Monday cut under Jay Joyce. The hook is sharp, but the lesson is sharper: trust your co-writers and write the truth the artist can live.

The ride doesn’t smooth out from there. Abram talks turkey hunts that led to Dylan Marlowe’s “Record High,” an Andy Grammer session that turned into his first major cut with “Red Eye,” and the wild “My Side of Town” saga—instant holds, a Morgan Wallen cut that missed the final tracklist, and a rebirth with Josh Ross. Along the way, we get field-tested advice for new writers: show up to writer rounds, know your role in the room, let simple ideas breathe, and don’t force doors that won’t open.

If you love the craft behind country hits, co-writing dynamics, and real talk about the highs and gut-punches of modern songwriting, this one’s for you. Subscribe, share with a songwriter friend, and leave a review to help more listeners find the show. What part of Abram’s journey hit you hardest?

A guitar from his uncle’s country band, open mics before he could legally walk into the bar, and a stubborn ear that learned by listening—Roman Alexander’s road to Nashville wasn’t polished, it was practiced. We sit down to unpack the exact moves that turned a Missouri kid into a touring artist and a credible songwriter: washing cars at an Audi dealership to meet gatekeepers, selling merch on a midnight bus to learn tour life, and sending a bold “manager” email that led to a hard no—then a full-circle label meeting years later.

The conversation dives into the writing grind at 126, where two-a-day sessions forged his sound and revealed the collaborators who fit. Roman breaks down how “Party Mode” was born on a retreat deck and found its way to Dustin Lynch, why “Between You and Me” became an 11-month mainstay on Spotify’s Hot Country and a launchpad for national touring, and how he thinks about choosing songs that are truly his. We talk Midwest Calling—the weather, the breakups, and the small-town weight that never leaves—and the stories behind “Way Over You,” “Mama Smoked Cigarettes,” and “Country Dreaming” with Old Dominion’s Brad and Trevor and writer Matt Jenkins.

There’s heart and humor here: the viral video of his mom hearing “Mama Smoked Cigarettes” for the first time, the door-to-door sorority play that packed rooms on college runs, and the Maui BMI night where Willie Nelson calmed his shaking hands with a quiet nod beside Kris Kristofferson. Beyond the hype cycles and algorithms, Roman makes a case for touring as the anchor, for songs with staying power, and for learning the business with the same intent as the craft. If you’re building an independent career, this is a blueprint you can use—and a reminder to enjoy the full-circle moments when they arrive.

Enjoy the episode? Follow, rate, and share it with a friend who loves great songwriting. Your reviews help us bring on more artists and stories you care about.

Some losses leave us searching for words where there are none. The sudden passing of Brett James Cornelius, along with his wife and her daughter, in a plane crash on September 18, 2025, has left Nashville's music community reeling in grief. This special episode stands as a raw, heartfelt tribute to a songwriter whose pen crafted some of country music's most enduring hits, and whose heart crafted friendships that defined the Nashville community.

Brett James wasn't just a Grammy-winning songwriter behind Carrie Underwood's "Jesus Take the Wheel," Kenny Chesney's "When the Sun Goes Down," or Dierks Bentley's "I Hold On"—he was a presence you felt. Born in Missouri and twice attempting medical school before answering Nashville's persistent call, Brett approached songwriting with humility that elevated everyone in the room. "Some days you write something nobody will ever hear," he once said, "and then one day you write 'Jesus Take the Wheel.' That's the job, that's the beauty."

This episode weaves through Brett's musical journey, from his self-titled solo album in 1995 to his 2020 EP "I Am Now," featuring the moving "True Believer." Through tears and memories, we explore the stories behind his biggest hits and the profound impact of his genuine character. The episode concludes with a poignant performance of "Fall Into His Hands," the last song shared when Brett and I performed together earlier this year—a fitting reminder that while we may never understand such profound loss, music remains our collective solace.

Join me in honoring a true Nashville legend whose voice may be silenced but whose songs will forever echo in the hearts of millions. Share his music, remember his spirit, and keep his family in your prayers as we navigate this unthinkable loss together.

Grammy-winning artist Colbie Caillat sits down for an intimate conversation about the winding road from MySpace sensation to seasoned songwriter. With her trademark warmth and authenticity, she reveals how music was always coursing through her veins—singing at the top of her lungs every morning as a child and eventually being guided toward songwriting by her father's wisdom that it would "be more meaningful."

The conversation takes us through the unexpected explosion of "Bubbly" that catapulted her career, to touring with John Mayer in 2009, to her transformative relationship with vulnerability on stage. "I was taught to try to be extroverted and don't let anyone know that you're nervous," Colbie shares, describing how writing "Try" became the turning point that freed her from hiding her true self. "I just tell the audience everything on stage now. It feels so nice."

Colbie's upcoming album "This Time Around" (releasing September 26th) reimagines her greatest hits as duets with artists including Maren Morris, Hillary Scott, Walker Hayes, and Mitchell Tenpenny—many of whom had personal connections to her songs before the collaboration. "Mitchell was so cute because when I asked him to sing on 'Realize,' he's like 'that's my favorite song, I sang it in high school,'" she recalls with genuine delight. The album also features three new original songs, including one written with Lee Brice and another featuring Maddie & Tae.

Whether discussing the creative process behind her Grammy-winning duet "Lucky" with Jason Mraz, her Christmas tour with best friend Gavin DeGraw, or the first song she ever wrote ("Someday," which she plans to release someday), Colbie's reflections on her journey offer wisdom for creators at any stage: "Trust yourself and have fun with it and really embrace who you are." Connect with Colbie at colbiecaillat.com to follow her continuing musical evolution.

The first time Abbie Callahan heard Dolly Parton perform live, something clicked. At just 14 years old, watching from the audience with her mother and grandmother, Abbie experienced what she describes as an epiphany: "I saw that and I was like, 'oh, that's what I want to do.'" That moment set her on a path from Iowa City to Nashville, where she's now carving out a distinctive space with what she calls "Kaleidoscope Country."

Abbie's debut EP "Grossly Aware" showcases her remarkable ability to blend Americana, indie pop, bluegrass, and folk into something uniquely her own. Her journey hasn't been straightforward—moving to Nashville during COVID meant isolation instead of the typical music scene immersion. Yet that solitude shaped her songwriting process, leading to deeply personal tracks like "I'll Bring Flowers," which she describes as "journaling when your therapist tells you to write in the morning."

When her playful, suggestive song "Mary Jane" went viral, it created both opportunities and pushback. Some questioned whether her music belonged in country, but Abbie turns criticism into creative fuel: "When someone says 'you can't do that,' I think, 'I have to prove everyone wrong.'" This determination has taken her from grueling nights playing Broadway bars until 3 AM (then attending 8 AM classes at Belmont) to performances at CMA Fest and Bonnaroo.

What stands out most about Abbie is her authenticity—her voice doesn't sound like anyone else's, and her lyrics reflect genuine experiences rather than manufactured emotions. As she prepares for her Americana Fest showcase and upcoming collaborations (including a reimagined "Mary Jane" with a special guest), she remains committed to the advice she'd give her younger self: "Try to be yourself more and not someone that people like, because that just doesn't work out."

Ready to experience Kaleidoscope Country for yourself? Stream "Grossly Aware" now and follow Abbie's journey as one of Nashville's most captivating new voices.

What does it take to go from waiting tables to writing chart-topping hits for country music's biggest stars? In this compelling conversation, songwriter Blake Pendergrass opens up about his remarkable year since his last appearance on the podcast – a year that's seen him secure 15 cuts on Morgan Wallen's latest album (including his first #1 hit), pen songs for Jelly Roll, Tucker Wetmore, and Post Malone, and have eight singles charting simultaneously on country radio.

Behind these impressive statistics lies a deeply human story of perseverance through doubt. Pendergrass shares how after 13 years in Nashville with minimal success, his faith kept him going when logic suggested otherwise. The emotional high point comes when he discusses "The Dealer," a song he wrote entirely by himself during a period of uncertainty. "I wasn't really planning on writing a full song," he reveals, his voice breaking slightly. "I was in a season of feeling defeated... I sat down essentially to prove to myself I can still write songs." That vulnerable moment produced a powerful track that became one of his proudest accomplishments.

The conversation delivers fascinating insights into the mechanics of modern country songwriting – from the collaborative process of creating Morgan Wallen's "Just In Case" with multiple established writers to pushing genre boundaries with Tucker Wetmore's "Brunette." Pendergrass explains how writing changes when working with artists at different career stages and how he approaches rooms with multiple strong creative voices. His perspective on balancing artistic exploration with commercial sensibility provides valuable wisdom for creators in any field.

Whether you're an aspiring songwriter, a music industry professional, or simply a fan curious about how your favorite songs come together, this episode offers an authentic glimpse into both the craft and the heart behind today's biggest country hits. Listen now to experience the stories behind songs that are shaping the soundtrack of modern country music.

From the rolling hills of Scotland to the hallowed circle of the Grand Ole Opry, Callum Kerr's musical journey defies conventional paths. Our conversation reveals the beautiful synchronicity of events that led this actor-turned-country artist to find his true calling.

Callum shares how his musical awakening happened at 17 when a Texas sports camp job unexpectedly introduced him to country music. "I was just blown away," he recalls of hearing artists like Dierks Bentley and Zac Brown Band for the first time. "This is the sound that I've been looking for." His authentic passion is palpable as he describes moving between acting jobs in the UK and musical adventures in the American South.

The pivotal turning point came when Callum landed a role as a Texas country singer on Fox's "Monarch" alongside Trace Adkins. Being in the studio with Nashville session players sparked something profound: "If I'm good enough to be in their TV show with a budget of 10 million per episode, maybe I could do this." This realization brought him to Nashville, where he immediately felt at home.

We dive deep into Callum's songwriting process, his philosophy of "best song wins" regardless of who wrote it, and the meaningful stories behind tracks like "Used to Love This Town" and "It Ain't Working" from his Dan Huff-produced EP. The conversation culminates with his emotional recounting of making his Grand Ole Opry debut—a dream realized on the very same day his EP was released.

Whether you're fascinated by the creative journey, drawn to authentic country storytelling, or simply love discovering artists on the rise, Callum's story will resonate. His final advice to his younger self speaks volumes: "If you like it, then it's cool. One day people are going to find that cool." Listen now and witness the beginning of what promises to be a remarkable career.

Cole Taylor's journey from small-town Georgia to Nashville success story perfectly captures the dreams that bring so many songwriters to Music City. Within just nine months of arriving in Nashville, Taylor landed a publishing deal that would launch a career filled with chart-topping hits for country music's biggest stars.

Growing up immersed in a rich musical tapestry—from Alan Jackson's storytelling to Lynyrd Skynyrd's southern rock—Taylor developed a versatile songwriting approach that makes him a sought-after collaborator. "My head is just a burnt CD of just anything and everything," he explains, describing how his diverse influences allow him to adapt to any writing room situation.

The stories behind Taylor's biggest hits reveal both his craftsmanship and the serendipitous moments that define songwriting. His first number one, "Sippin' on Fire" with Florida Georgia Line, came from a writing session with Matt Dragstrom that later received input from veteran songwriter Rodney Clawson. Taylor received the life-changing news while turkey hunting back home in Georgia—a fitting full-circle moment for the small-town songwriter making it big.

Taylor's catalog includes standout duets like "Home Alone Tonight" (Luke Bryan and Karen Fairchild) and "You Me and Whiskey" (Justin Moore and Priscilla Block), showcasing his ability to create musical conversations that resonate with listeners. His thoughtful approach to songwriting balances commercial appeal with genuine emotion, as evidenced in songs like "Good News Sold" and "Can't Kill a Prayer."

Beyond his songwriting success, Taylor gives back through "Playing Through," a company he co-founded that combines his passions for golf and music while raising money for charities. This entrepreneurial spirit and commitment to community reflect the values that have guided his career from the beginning.

For aspiring songwriters, Taylor's advice is refreshingly straightforward: "Keep showing up" and "Get through the bad songs, find the great ones." His journey proves that with talent, persistence, and the right connections, those Nashville dreams can absolutely come true.

Braden Jamison's voice hits you immediately – authentic, rooted in tradition, yet distinctly his own. The Oklahoma native's path to Nashville wasn't straight, having grown up playing four sports simultaneously before making the pivotal decision to quit basketball his junior year to pursue music. That choice led to an unforgettable opportunity: opening for Toby Keith after just one band rehearsal.

After moving to Nashville in 2020 to attend Belmont University, Braden embraced the songwriter's grind, collaborating with anyone willing while developing thick skin through critique. His persistence paid off when a publishing class introduction to Chris at Seagull Music led to an internship that evolved into his first publishing deal in 2024.

The stories behind Braden's songs reveal both his creative process and lived experience. "CattyWampus," a standout track from his May EP release, began as a title nobody wanted to write until Lee Star embraced the concept, resulting in what Braden describes as his favorite song sonically. "Suits Me Just Fine" captures the reality of driving between gigs with barely enough money for gas while watching friends pursue more lucrative careers – "Ain't nobody getting rich, sometimes we play for tips." Meanwhile, "When It Comes to You" emerged victorious after Braden wrote three consecutive love songs, searching for the perfect track to complete his project.

Braden's band name "The Neon Strangers" came about accidentally when his brother jokingly suggested it during a show introduction. Now touring regularly, he finds the greatest reward in fans singing his lyrics back to him and sharing how his music has become part of their lives.

With his distinctive voice, thoughtful songwriting, and hard-earned wisdom ("The only way it for sure doesn't happen is if you stop doing it"), Braden Jamison represents country music's promising future. Listen and discover an artist whose honky-tonk heart and genuine approach to his craft will leave you wanting more.