What does it really take to build a career in music that lasts?

After more than two decades on the road, Drew Holcomb knows that making great music is only part of the job.

Just before taking the stage in Charleston with Ellie Holcomb to open for NEEDTOBREATHE, Drew joins Americana Curious to reveal the side of the music business fans rarely see.

He shares how becoming a professional musician forced him to become an entrepreneur—learning marketing, design, payroll and business management along the way. He also opens up about the ventures that worked, the ones that lost money, and why he eventually realized that what he loves most is still writing songs, recording them and taking them on the road. Drew Holcomb 2 Final transcrip…

Drew also takes us inside:

• Why it took him and Ellie more than 20 years to make an album together
• How their pandemic Kitchen Covers helped lead to Memory Bank
• Taking the spirit of Moon River Music Festival out to sea
• The difference between headlining and winning over someone else’s audience
• Why authenticity may be the best way to make new fans
• The surprising way he talks to his kids about the music they listen to
• What comes next as Drew prepares to step back from touring and make new music

It’s a candid look at music, marriage, entrepreneurship, failure, creativity—and what it actually takes to build a life around doing what you love.

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Jonah Kagen has racked up over half a billion streams, scored a Billboard #1 hit with "God Needs the Devil," and sold out headline shows across the globe. But as he shares on Americana Curious, the commercial accolades didn't bring validation—they forced him to isolate, face his inner demons, and dig into his darkest songwriting yet.

In this raw, unfiltered conversation, Jonah joins host Ben Fanning (Zach Schultz couldn't join us for this one) to talk through:

• The #1 Hangover: Why chart success didn’t make his next record any easier, and why he views making music as a job of service rather than ego.
• Life on the Road: Totaling his truck, living nomadic in a modified Airstream studio, and recording in a stranger's front yard.
• Meeting Dave Matthews: How a custom guitar commission led to an intimate writer's round, tequila in pajamas, and an invitation to open at The Gorge.
• The New Album: The deeply personal, late-night creative marathons behind Eternity of Everything, and why the certainty of death scares him far less than love.
• Crowd Etiquette: The specific things fans need to start (and stop) doing at his high-energy live shows.

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Andrew Sa grew up obsessed with Patsy Cline. Today, he’s challenging one of country music’s oldest assumptions: who gets to belong.

The Chicago country artist’s debut album, American Rough, blends the sounds of classic country with deeply personal songs about love, masculinity, identity, and belonging. And Andrew isn’t asking permission to be part of the genre: “I’m not separate and I’m not different and I belong there.”

Andrew joins Ben Fanning and Zach Schultz to share the childhood story behind his connection to sad country songs, how Rufus Wainwright gave him “permission to have this dream,” and the unforgettable moment Lavender Country’s Patrick Haggerty grabbed him by the shoulders and told him, “I see you now.”

They also dig into the meaning behind American Rough, building bridges through music, where queer country fits within Americana, and Andrew’s upcoming opportunity to honor John Prine at the Chicago Theatre.

It’s a conversation about finding your voice, claiming your place, and why the best country music can make room for more stories...not fewer.