Stories Behind the Songs

Time to close the books on a huge year and open the door to an even bigger one. We step back to celebrate what your support made possible at the Listening Room—862 shows, 150,000 guests, and a stack of songs that went from our stage to number one—while setting the stage for what’s next in 2026.We share why the Listening Room remains a passion project at its core and how community keeps pushing the music forward. Then we unveil plans for our 20th anniversary at the historic Ryman Auditorium on March 3, 2026, with a heavyweight lineup: Hardy, Jo Dee Messina, Mitchell Tenpenny, Blessing Offor, Jordan Feliz, plus a powerhouse bench of hitmakers like JT Harding, Rob Williford, Phil Barton, James Slater, Matt Jenkins, Brian Davis, Wendell Mobley, and Lee Thomas Miller. Expect stories behind the songs, surprise guests, and the kind of moments that turn a great night into a landmark memory.We also tease a major project two years in the making that’s almost ready to announce—built to connect artists, writers, venues, and fans in smarter, more meaningful ways. Programming will flex a bit early next year as we lock the final pieces, but the conversations won’t stop. February brings our second annual Boots on the Water cruise to Cozumel with Clint Black, Rodney Atkins, Terri Clark, Diamond Rio, BlackHawk, Chris Cagle, Phil Vassar, Deana Carter, David Lee Murphy, and more, plus TLR songwriting favorites including Liz Rose, Adam Craig, Emmett Stevens Jr., Bridgette Tatum, and Rachel Thibodeau. We’ll record at sea and bring you deck-side stories, fresh performances, and the kind of candid moments only a cruise can spark.If you love country music, songwriting, live shows, and the stories that turn a hook into a hit, you’ll feel right at home here. Grab your seats for the Ryman at ryman.com, book your cabin at bootsonthewatercruise.com, and come ride with us into 2026. If this episode moved you, tap follow, share it with a friend, and leave a quick review to help more fans find the music and the stories behind it.

A farm town kid with a tiny amp, a bandana from Stagecoach, and a promise to take one more swing at the dream—Tyler Rich sits down with us to unpack the road from Northern California to Nashville and what it costs to make something that truly feels like you. We trace the early wins and wipeouts: a record deal at nineteen, years of touring with homework due on a bus, an economics degree finished at warp speed, and the moment he turned down a safe, salaried future to chase a riskier one that wouldn’t let him sleep.We go inside the writing rooms and the edges where craft gets sharpened. Mentors like Daryl Brown pushed his melodies and choices with sharp, priceless notes, while a DIY marketing blitz—thousands of cards handed out at shows and a brave DM hustle—built real fans one by one. That grit fueled a fast move to Nashville, where a culture of friendly competition and structured writing turned instinct into volume and voice. From there, the double album took shape: Poppy and Iris, a project anchored to state flowers and a life split between two homes. Cowboy Tears lifts like an anthem but breaks like a diary, a tribute to distance, devotion, and a bandana that never left his pocket. Redwood grows from wildfire science into a resilience song, proof that some things only get stronger after the burn.Independence was the next leap. Tyler walks through leaving a label, rebuilding his team with fresh eyes, and releasing twenty-plus songs that aim for the gut instead of the middle. The connection shows up in rooms—fans crying, him crying—especially when Dogs Don’t Die helps people carry the love that remains. That song sparked a new lane: children’s books that translate courage, grief, and selfhood for young readers. We preview Leave The Wolf Wild and Fred Under The Bed, and look ahead to a co-headline tour with a rock powerhouse designed to bridge country heart and rock muscle.If you love stories about craft, risk, and the long route to your real voice, this one’s for you. Hit play, share it with a friend who needs courage today, and if it resonates, follow the show, leave a review, and tell us which song hit you hardest.

A last-minute writing invite, a young artist with star power, and a chorus that had to carry the whole story—Ava Sapelsa walks us through how a room with Jamie Kenny, Trent Dabbs, and Max McNown turned into a multi-format hit climbing hot AC, pop, and country radio while living on the Billboard charts for months. We trace the journey from poetic verses to a clear “brown eyes” hook, why the melody stretches across male and female ranges, and how a strong chorus can translate from TikTok buzz to radio momentum without losing its heart.From there, we rewind to Evanston and Montana, where cover sets and country storytelling shaped Ava’s instincts, then fast-forward to Nashville writers’ rounds as a crash course in modern songcraft. Ava shares the strategies behind “Salt, Lime & Tequila,” a Zoom-era co-write with Ryan Griffin and Jason Massey that snowballed from a rough title to SiriusXM The Highway’s most-played song, and how TikTok, smart pitching, and timing opened the door to radio. We also break down her outside cut with Carly Pearce on Hummingbird, proving how a clean concept and an honest lyric can move from demo to record in a week when everything aligns.Beyond charts and cuts, Ava brings purpose to Music City through Hope on the Row, a nonprofit serving unhoused neighbors with food, supplies, and pathways to stability—powered by volunteers from across the music industry. It’s a reminder that enduring careers are built on craft, community, and consistency. If you’re chasing better choruses, clearer concepts, or a stronger network, you’ll find practical takeaways and candid stories you can use on your next write.Enjoy the episode, then subscribe, share with a songwriter friend, and leave a review so more music lovers can find these stories.

A riff can change a room. That’s the spark Jerry Flowers chases as he walks us through the real stories behind hits for Sam Hunt, Ryan Hurd and Maren Morris, Old Dominion, Morgan Wallen, Keith Urban, and more—plus the hard turns only a long road can deliver. From the first glint of House Party’s pre-chorus to the soul-steeped simplicity of Chasing After You, Jerry shows how tempo, tone, and lived experience shape songs that last.We dig into the writing retreat that birthed Kinfolks, the late verse rewrite that made radio, and the rare week-long sprint that got Last Drive Down Main to Morgan Wallen. Jerry opens up about being fired mid-session after decades with Keith Urban, then choosing to finish Water My Flowers—and how Old Dominion’s cut turned a gut-punch day into a keeper. He shares the unexpected lineage between old-school country and R&B, why he’s often the “energy guy” in the room, and how a great demo can sit for years before the right voice brings it to life.There’s touring wisdom here too: from playing on an airport baggage carousel in Tamworth to facing 800,000 people in Philly, the takeaway is clear—be the best hang, use your downtime, and build a second lane with writing or production. Jerry’s closing advice to new writers and artists lands like a compass: figure out who you are, defend it, and let time reward the work. If you love songwriter stories, Nashville craft, and the moments where resilience becomes melody, this one hits home.If this conversation moved you, follow the show, share it with a friend, and leave a quick review. It helps more music fans find these stories and keeps the conversations coming.

A riff can change a room. That’s the spark Jerry Flowers chases as he walks us through the real stories behind hits for Sam Hunt, Ryan Hurd and Maren Morris, Old Dominion, Morgan Wallen, Keith Urban, and more—plus the hard turns only a long road can deliver. From the first glint of House Party’s pre-chorus to the soul-steeped simplicity of Chasing After You, Jerry shows how tempo, tone, and lived experience shape songs that last.We dig into the writing retreat that birthed Kinfolks, the late verse rewrite that made radio, and the rare week-long sprint that got Last Drive Down Main to Morgan Wallen. Jerry opens up about being fired mid-session after decades with Keith Urban, then choosing to finish Water My Flowers—and how Old Dominion’s cut turned a gut-punch day into a keeper. He shares the unexpected lineage between old-school country and R&B, why he’s often the “energy guy” in the room, and how a great demo can sit for years before the right voice brings it to life.There’s touring wisdom here too: from playing on an airport baggage carousel in Tamworth to facing 800,000 people in Philly, the takeaway is clear—be the best hang, use your downtime, and build a second lane with writing or production. Jerry’s closing advice to new writers and artists lands like a compass: figure out who you are, defend it, and let time reward the work. If you love songwriter stories, Nashville craft, and the moments where resilience becomes melody, this one hits home.If this conversation moved you, follow the show, share it with a friend, and leave a quick review. It helps more music fans find these stories and keeps the conversations coming.