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Should've Been A Cowgirl
Jenna Heideman
45 episodes
21 hours ago
On Should’ve Been A Cowgirl, Jenna keeps you in the know on all things country music and western lifestyle. SBAC is your go-to source for country music entertainment, interviews with artists, rodeo athletes, and Western Influencers. Giddy up!
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Music Interviews
Music
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All content for Should've Been A Cowgirl is the property of Jenna Heideman and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
On Should’ve Been A Cowgirl, Jenna keeps you in the know on all things country music and western lifestyle. SBAC is your go-to source for country music entertainment, interviews with artists, rodeo athletes, and Western Influencers. Giddy up!
Show more...
Music Interviews
Music
Episodes (20/45)
Should've Been A Cowgirl
Should've Been A Cowgirl w/ Kyle Park

Should've Been A Cowgirl w/ Kyle Park

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1 month ago
29 minutes 31 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Briggs Madsen

This week on Should’ve Been a Cowgirl, we’re in Nashville for Stampede Days with PBR bull rider Briggs Madsen. Briggs takes us back to his rodeo roots in Honeyville, Utah, where his entire family has been part of the sport—from broncs to barrel horses. We talk about how watching 8 Seconds sparked his love for bull riding, what it was like breaking into the PBR, and even how he ended up on the same team as his younger brother.Briggs also opens up about balancing married life with life on the road, why Utah is one of the best-kept rodeo states, and his favorite way to experience new cities (hint: it’s not Broadway).If you love rodeo, family stories, and a behind-the-scenes look at PBR life, this episode is for you!

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2 months ago
36 minutes 40 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Austin Richardson

00:00 – Nashville Stampede Days Kickoff
Host welcomes listeners live from Nashville and introduces guest Austin Richardson.

01:30 – Nashville Vibes
Austin shares what it’s like being back in Music City and his favorite parts of exploring Broadway.

03:15 – From Dirt Bikes to Bull Riding
Austin explains how motocross shaped his early life before bull riding caught his attention.

06:00 – Going Pro
How bull riders earn their pro card, work their way through Velocity and Touring Pro events, and reach the PBR Unleash the Beast tour.

11:45 – Early Career Challenges
Austin reflects on his struggles in his first years, finding consistency, and the turning point in 2020.

15:20 – The Draft & Team Competition
Explaining the PBR team format, the draft process, and Austin’s experience being traded before landing in Nashville.

20:10 – What Makes a “Rank” Bull
The difference between “dirty” unpredictable bulls and the smoother, powerful champions like Wolf Paw and Bruiser.

24:00 – Scoring Breakdown
How judges score bulls and riders, what fans should look for in a great ride, and what a “re-ride” means.

30:15 – Game Day Routine
Austin walks through a Stampede weekend—from practice, preparation, and starching jeans, to the adrenaline of intros and competition.

38:00 – Behind the Chutes
What really happens in the back pens: strategy, coaching, challenges, and the little details fans might miss.

44:40 – Training & Team Facilities
How Nashville’s training center in Texas keeps the team sharp, with practice bulls, workouts, and film study.

50:15 – Life Off the Road
Friendships, rivalries, golf games, and how bull riders balance competition with camaraderie.

56:30 – Dallas Travel Tips
Austin’s picks for visitors to Texas, including Fort Worth Stockyards and the Drover Hotel.

01:01:00 – Fan Experience at Stampede Days
Why the Nashville crowd is one of the rowdiest, the autograph sessions, and what fans can do to show love for the team.

01:05:00 – Wrapping Up
Closing thoughts, laughs about childhood photos, and a nod to Austin’s growing career in PBR.

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2 months ago
26 minutes 9 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Clay Aery

Should've Been A Cowgirl w/ Clay Aery

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5 months ago
22 minutes 50 seconds

Should've Been A Cowgirl
Shoudl've Been A Cowgirl w/ Wynn Williams

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!

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8 months ago
30 minutes 11 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Caden Gillard

Caden Gillard’s Journey from Bull Riding to Music

In 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.

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9 months ago
38 minutes 12 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl - 2025 Solo Episode

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!

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9 months ago
10 minutes 55 seconds

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

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

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11 months ago
26 minutes 34 seconds

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

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

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11 months ago
26 minutes 46 seconds

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

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

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12 months ago
32 minutes 8 seconds

Should've Been A Cowgirl
SBAC: Jenna LaMaster Interview

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)

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1 year ago
26 minutes 32 seconds

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

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


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1 year ago
47 minutes 57 seconds

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

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

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1 year ago
47 minutes 57 seconds

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

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

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1 year ago
47 minutes 57 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Carson Jeffrey (Rural Radio Replay)

Should've Been A Cowgirl w/ Carson Jeffrey (Rural Radio Replay)

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1 year ago
47 minutes 54 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Dzaki Sukarno (Rural Radio Replay)

RURAL RADIO REPLAY w/ Dzaki Sukarno

This week on SBAC we sit down with Dazaki Sukarno and dive into his music, growing up in New Mexico, and his experience on American Idol. Give it a listen!

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1 year ago
47 minutes 57 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Charly Reynolds (Rural Radio Replay)

Rural Radio Replay w/ Charly Reynolds

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1 year ago
47 minutes 57 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Kylie Frey (Rural Radio Replay)

Should've Been A Cowgirl w/ Kylie Frey (Rural Radio Replay)

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1 year ago
47 minutes 53 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl (Tribute to Toby Keith AKA Big Dog Daddy)

This week on SBAC we dive into our favorite Toby Keith songs and memories!

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1 year ago
47 minutes 56 seconds

Should've Been A Cowgirl
Should've Been A Cowgirl w/ Drake Milligan (Rural Radio Replay)

This week on Rural Radio, we sit down with Drake Milligan to talk about his experience impersonating Elvis, playing Billy Bob's Texas, and his upcoming tour dates with Cody Johnson.


DRAKE MILLIGAN BIO: Drake Milligan burst onto the national music stage entering the Billboard Emerging Artists Chart at #5 after dominating iTunes. His single “Sounds Like Something I’d Do” has been streamed 32 Million times. The Fort Worth native charted back-to-back #1 hits on the iTunes Country Songs Chart, #1 on iTunes All-Genre Chart and reclaimed the #1 spot on iTunes Country Albums Chart, all while simultaneously holding positions #1, #2, #3 and #5 on iTunes Country Video Chart.In the UK, Milligan’s debut album spent 11 consecutive weeks in the Top 20 of the Official Country Artists Albums Chart.Milligan is a student of classic Country music with the swagger of early Rock ‘n’ Roll. He’s an electrifying entertainer who is packing Country fans into clubs night after night on tour. Milligan cites George Strait and Elvis Presley – the King of Country and the King of Rock ‘n’ Roll – as musical heroes. His unique twist of traditional Country has been embraced by fans, peers and the media alike. Milligan has performed on The Kelly Clarkson Show, The Grand Ole Opry, Stagecoach and CMA Music Festival. He has earned high praise from People, BBC, USA Today, Parade, American Songwriter, CMT.com, Billboard, ET, Access Hollywood, Cosmopolitan, Cowgirl Magazine and Taste of Country.His debut album Dallas/Fort Worth released via Stoney Creek Records, was co-produced by award-winning Tony Brown and Brandon Hood.

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1 year ago
47 minutes 57 seconds

Should've Been A Cowgirl
On Should’ve Been A Cowgirl, Jenna keeps you in the know on all things country music and western lifestyle. SBAC is your go-to source for country music entertainment, interviews with artists, rodeo athletes, and Western Influencers. Giddy up!