In episode 241 of Outside the Round, host Matt Burrill sits down with rising country artist and influencer Katie Dempsey, better known as Demps. From a tough upbringing to becoming a single mom, viral content creator, and now a full-blown artist, Demps opens up about her wild ride to Nashville. She shares how motherhood shapes her songwriting, how her friendship with Priscilla Block keeps her grounded, and what it's like transitioning from bail bondsman to breakout country star. With new music on the way and her first headlining tour ahead, this conversation dives into resilience, hustle, and heart.

Follow on Social Media: 

Demps: @therealdemps93

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy 

In Episode 240 of Outside The Round, host Matt Burrill sits down with Gannon Fremin of Gannon Fremin & The CCREV to dive into his rise from Oklahoma’s Red Dirt scene to national stages. Gannon shares how the Stillwater music community shaped his genre-blending sound, the role live shows have played in growing a loyal fanbase, and the meaning behind his recent signing with Warner Records. They talk about the energy of CalfFry Festival, what it’s been like touring with Gio and The Hired Guns, and how those road-warrior moments have shaped both his music and mindset. From writing songs with emotional grit to balancing band life and food stops across America, this episode is a look into the evolution of a modern Red Dirt artist bridging the gap between Oklahoma authenticity and Nashville opportunity.

Follow on Social Media:

Gannon Fremin: @fremingannon | @gannonfreminccrev

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy 

On episode 239 of Outside the Round, host Matt Burrill sits down with rising country artist Tommy Acker to talk about his journey from Texas to Nashville and his unexpected path from baseball and biology to the country music stage. Originally planning for dental school, Tommy found new purpose through songwriting and performance, launching his career with the help of social media platforms like TikTok. His first viral hit opened the door to mentorships with artists like Hannah McFarland and Jessi Alexander, and eventually to opening for Meg Moroney. Tommy shares insights on his competitive nature from his baseball days, the emotional side of leaving home to pursue music, and the growth that comes with embracing Nashville’s collaborative and supportive environment. The conversation covers his songwriting process, building connections in the industry, developing his sound, and the importance of patience and persistence. With a clear vision and growing momentum, Tommy Acker is making his mark as one of country music’s most exciting new voices.

Follow on Social Media:

Tommy Acker: @Tommyacker

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy 

On episode 238 of Outside the Round, we welcome Philip Bowen, the incredibly gifted fiddle player and songwriter from West Virginia. Philip shares his inspiring journey from blue-collar roots to building a thriving music career, highlighting how COVID-19 unexpectedly opened doors through platforms like TikTok. He discusses the importance of authenticity in songwriting, the balance between family life and touring, and his memorable performance on NPR’s Mountain Stage, a major turning point in his career. In this heartfelt conversation, Philip reflects on the power of Appalachian storytelling, how his culture and upbringing influence every note he plays, and the personal growth that came with transitioning from musician to full-fledged artist. We dive into his upcoming album Appalachia Forever, the support of community and fans, and the value of simplicity and connection in both cooking and music. Whether it’s fiddle solos, fan interactions, or the grind of tour life, Philip brings deep gratitude and wisdom to every part of the journey. 

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Philip Bowen (Guest): @philipbowenmusic

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy 

On episode 237 of Outside the Round, we sit down with Sevy to unpack his journey from Texas to Nashville, where his move proved pivotal in shaping both his career and sound. Balancing the duality of his artistic identity as Andrew and Sevy, he shares how years of experimentation, collaborations, and life on the road helped define the genre-blending music he’s making today. From his time on The Voice to his current role as guitarist on the road for Tayler Holder, Sevy dives into how humor, emotional honesty, and fan connection drive his creative process. We explore the power of social media—especially pre-saves and short-form video—in building momentum around upcoming releases, and how community and friendships in Nashville and through Raised Rowdy have opened unexpected doors. Sevy shares stories from past DIY college tours and how creating space for fun and deep connection in his shows has become core to his mission. With new music on the horizon, we talk about the importance of being vulnerable in songwriting, embracing the second verse innuendos, and staying true to the joy that got him here in the first place.

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Sevy (Guest): @itsbrokesevy 

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy 

On episode 236 of Outside the Round, host Matt Burrill sits down with Vincent Mason, the Georgia-born country artist behind the hit song Hell is a Dance Floor. Vincent reflects on his journey from Roswell, GA to the heart of the Nashville music scene, sharing how one song changed everything and how the support of a strong community has shaped his career. He dives into the influence of his Georgia upbringing, the surreal experience of playing the Grand Ole Opry, and the lessons learned touring with Gavin Adcock. The conversation covers everything from early inspirations and fraternity life to the evolution of his songwriting, the transition into album production, and building a supportive band dynamic while headlining sold-out shows. With a blend of humor, humility, and heartfelt insight, Vincent offers an honest look at the grind, growth, and gratitude that define his journey as one of country music’s most exciting new voices.

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Vincent Mason (Guest): @vincentmason

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy

On episode 235 of Outside the Round, we sit down with Ashland Craft to talk about her inspiring journey from small-town South Carolina to Nashville’s country music scene. Ashland shares the story behind her new album, Dive Bar Beauty Queen, a project that captures her authentic spirit and the ups and downs that shaped her path.She reflects on the importance of community and support, the personal significance of the number 11, and how touring with established artists helped her grow as a performer. Ashland opens up about the excitement of turning 30, trusting her gut, and redefining success as happiness and fulfillment rather than financial gain. From her strong connection with fans to her life on the road (and love for her dog, Dolly), Ashland offers a real, heartfelt look into her evolving career and personal journey.With stories of crafting outside of music, embracing the moment, and finding balance between her chill and wild sides, this episode is a celebration of passion, growth, and authenticity.

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Ashland Craft (Guest): @ashlandcraft

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy

On episode 234 of Outside the Round, Matt sits down with  Lil Man J to explore his powerful journey from overcoming early health struggles to building a music career rooted in authenticity, resilience, and positivity. He opens up about the challenges he's faced, the role of family support, and how music became both a creative outlet and a path to healing. The conversation dives into the emotional core of songwriting, the importance of blending genres, and how social media can both inspire and complicate a young artist’s mental health. Lil Man J shares how personal stories drive his content, how he's learned to balance fame with life, and the joy of creating music that resonates with fans. With themes of self-discovery, gratitude, and staying true to one’s purpose, this episode offers an uplifting look at an artist using his platform to spread light and connect through vulnerability!

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Lil Man J (Guest): @

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy

On episode 233 of Outside the Round, Matt Burrill sits down with rising country artist Preston Cooper to talk about his journey from delivering mail in Fredericktown, Ohio, to delivering heartfelt songs on stages across the country. Preston reflects on growing up in a small farming town, his pivotal breakout show in Toledo, and the whirlwind that followed—including the game-changing CRS Luncheon and his fast-paced radio tour.He opens up about the influence of classic rock and country on his sound, his tight-knit collaboration with the Warren Brothers, and the 12-track debut album 'Toledo Talkin' they’ve created together. Preston shares insights into the realities of navigating the music industry at a young age, the importance of family support, and how mental health, hiking, and staying connected to his roots keep him grounded. From dreams of the Opry to advice for aspiring musicians, this conversation offers an inspiring look at an artist on the rise—and the heart behind the hustle.

Follow on Social Media:

Preston Cooper (Guest): @prestoncoopermusic

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy

On episode 232 Matt sits down with rising country artist Tyler Nance to explore his incredible journey from small-town welder in Missouri to the Nashville music scene. Tyler opens up about picking up a guitar out of boredom, going viral on TikTok, and signing with Alamo Records, which helped launch his career. He reflects on the creative process behind his debut EP, Wasted Chances, a collection of raw, personal stories that capture the highs and lows of his journey so far. The conversation dives into life on the road—including living in a camper—touring with Kidd G, and how performing live quickly turned into a full-blown passion. Tyler speaks candidly about overcoming social anxiety, navigating new relationships, and the importance of mentorship and community in Nashville. From welding to writing songs that connect on a deep level, Tyler’s story is a testament to personal growth, taking risks, and making the most of second chances.

Follow on Social Media:

Tyler Nance (Guest): @tylernancemusic

Matt Burrill (Host): @mattburrilll

Outside The Round (Podcast): @outsidetheround

Raised Rowdy (Network): @raisedrowdy