Trey Calloway – 7/20/26

You can hear it in Trey Calloway’s voice: the grind is still there, but something has shifted. The work feels more focused, the circle is tighter, and the next steps look a lot more like a real Nashville plan than a hopeful guess. Jay Franze sits down with Trey to talk through the behind-the-scenes moves that actually change a country artist’s trajectory: signing with manager Jerry Hines, learning how to lead with confidence, and building a team that believes in you when you are tempted to doubt yourself.

We dig into the advice Trey is getting from Jerry and Craig Morgan, especially the part most artists struggle with: stop selling yourself so hard and start trusting what you do well. Trey shares how he used to turn rejection inward, how that mindset can poison your momentum, and why positivity matters when you are the “CEO” of your own career. If you care about artist development, music industry mentorship, and the mental health side of chasing big goals, this conversation gets specific fast.

Then we go deep on the practical craft: working with producer Phil O’Donnell, recording at Soundstage Studios on Music Row, and why collaboration with great players can elevate a record without losing the heart of the song. Trey also breaks down a huge weekend as Craig Morgan’s special guest, what the tour bus life taught him, and how a single onstage introduction can translate into real social media growth.

We close with big news about Broken Compass and the broader mission of building careers the right way, plus plenty of road stories along the way. Subscribe for more conversations like this, share it with a friend who loves country music, and leave a review that tells us what part hit you the hardest.

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David Chatfield, Founder and CEO of Harmony Records

Streaming promised unlimited music, but it also trained us to treat songs like disposable wallpaper. We sit down with Harmony Records founder and CEO David Chatfield to talk about what that shift costs artists and listeners, and why he thinks the next wave is about bringing music back to being an experience you choose, not noise that happens to you. 

David walks us through building a record label from the ground up, from the early 1980s world of $125,000 recording budgets and indie distribution to today’s reality of home studios, cheaper lockouts, and the brutal competition of constant new releases on Spotify. We dig into what actually holds up across every era: writing better songs, crafting memorable hooks, arranging music for records, and following through on promotion when things inevitably go sideways. 

Then we get practical about music marketing and artist development. David explains why a million streams can still mean nothing if you do not tour, how a small base of superfans can fund a real career through merch and direct support, and why physical media like CDs and vinyl is trending again when the packaging gives people something to hold, read, and keep. We also talk legacy artists, catalog revival, cinematic music videos, radio strategy, and thinking globally about where fans still buy records. 

If you got value from this conversation, subscribe, share it with a friend, and leave a review so more artists and music fans can find the show. What part of today’s music business do you want us to tackle next?

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Tropidelic

A band that adopts a highway, cleans it with fans, then goes straight back to building a tightly synced live show is the kind of story we can’t stop talking about. I’m joined by Rex Larkman, drummer for Tropidelic, for a conversation that moves from Cleveland pride to the real mechanics of modern touring, with plenty of laughs and hard-earned lessons in between. 

We get into the Cleveland music scene and how a “Lake Erie ocean” mindset can fuel a band whose sound blends reggae rock, funk, hip-hop, and high-energy drumming. Rex breaks down the drummers who shaped him, from Neil Peart and Trey Cool to Joey Jordison and Carter Beauford, and explains how he approaches recording versus performing so the parts serve the song but the stage still hits like a rush. 

Then we go deep on the gear and the why behind it: click track philosophy, backing tracks used as layered support rather than shortcuts, and Rex’s practical Roland SPD-SX setup with count-offs and a kill switch for the nights when tech fights back. We also talk tour life, Warped Tour chaos, rain-soaked shows, and the surreal feeling of playing Red Rocks, plus the “basement of Red Rocks” vibe at The Caverns. We wrap with Tropidelic’s new album First Light, DIY music video production, and a shout-out to the unsung heroes behind every great show. 

If you like artist interviews, touring stories, drumming talk, and behind-the-scenes music production, subscribe, share this with a friend, and leave a review. What’s the best live venue you’ve ever been to?

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