Should've Been A Cowgirl

Wynn Williams, a Texas-based musician, discusses his musical journey, including his transition from rodeo to music. Williams highlights his background in rodeo, explaining the mechanics of steer wrestling and the financial aspects of competing. Giddy up!

Caden Gillard’s Journey from Bull Riding to MusicIn the first episode of the year, Jenna welcomes singer-songwriter Caden Gillard to the podcast. They dive into Caden’s unique path to music, starting with his upbringing in a rodeo family, his early love for bull riding, and how an unexpected twist led him to a music career.Caden shares how skateboarding, sports, and his dad’s influence shaped his childhood before a leukemia diagnosis in his freshman year of high school changed everything. During his time in the hospital, he taught himself to play guitar, discovering a passion for music while performing for nurses and fellow patients. After recovering, he returned to bull riding, eventually competing in PRCA events.Along the way, his love for music never faded. Playing his guitar at rodeos and sharing songs online led to unexpected opportunities. He also opens up about his brief stint in college, majoring in music before ultimately deciding to pursue his passion outside the classroom.This episode is packed with inspiring stories of resilience, chasing dreams, and the unexpected paths that lead us to where we’re meant to be.

Welcome to 2025 and the first solo episode of Should've Been A Cowgirl! In this episode, we dive into the exciting plans for the podcast this year, including a commitment to consistent monthly episodes featuring incredible guests. From Texas country artists like Wade Bowen and Randy Rogers to songwriters and rodeo athletes, we're ready to share their stories and celebrate their journeys. Jenna reflects on her seven-year podcasting journey, from its early days to transitioning off Rural Radio and into a video-focused format. She also recaps her NFR experience, sharing highlights like Cowboy Christmas, outfit wins and misses, shopping tips, and unforgettable live performances by Cody Johnson and Ryan Bingham. Join us as we embrace the new year with big dreams, meaningful conversations, and plenty of country music and rodeo inspiration!

Should've Been A Cowgirl: Road to the NFR w/ Mae Estes

Should've Been A Cowgirl: Road to the NFR w/ Kylie Frey

Should've Been A Cowgirl: Road to the NFR with SJ McDonald

WELCOME TO SHOULD'VE BEEN A COWGIRL! This week, we have an interview with cowgirl and country artist Jenna LaMaster. Introduction (0:00 - 2:45) Journey into Music and Nashville (2:45 - 6:13) Support System & Community in Nashville (6:13 - 8:57) Performing at the Ryman (8:57 - 11:54) New Music Release (11:54 - 15:14) Personal Life (15:14 - 18:03) Truth is.. confessions! (18:05 - 20:53) Cowboy Coffee Playlist Recommendations (20:53 - 26:32)

Should've Been A Cowgirl w/ Justin Adams (Rural Radio Replay)

Should've Been A Cowgirl w/ Elvie Shane (Rural Radio Replay)

Should've Been A Cowgirl w/ Alex Miller (Rural Radio Replay)