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There’s an idea we all want to believe. If you’re talented enough, you’ll make it.

This week on Here’s What We Know, we sit down with singer-songwriter Trey Calloway, a rising country artist navigating the reality of building a career in today’s music industry. And what we uncover is something a lot of people don’t want to admit: Timing matters more than talent.

We talk about country stars like Jason Aldean and Eric Church, artists who feel inevitable now but weren’t always. There were years where nobody knew who they were, years where it could have gone the other way.

Because when you really look at success in the music industry, you start to realize something. It doesn’t happen overnight, and it doesn’t happen just because someone is talented.

It happens when everything lines up. Talent. Timing. Opportunity. And readiness.

Miss one of those, and the outcome can look completely different.

If you’ve ever wondered what it really takes to make it in country music, why some artists break through and others don’t, or how timing shapes success in the music industry, give this episode a listen!

In This Episode:

• Why some incredibly talented artists never break through
• How timing, readiness, and life experience all collide
• The reality of making money in music today
• Why success often comes later than expected
• And what keeps someone going when it would be easier to quit

This episode is sponsored by:

Sterling Oak Cabinetry

Reed Animal Hospital

Bio:

Trey Calloway is a singer/songwriter born and raised in North Carolina. The son of a preacher man, Trey grew up singing in church and was a seasoned performer by the age of 10. Although southern and contemporary gospel were his first musical loves, he was instantly mesmerized by the sounds of country music after hearing a Garth Brooks Greatest Hits album his parents bought for him. A deep understanding and passion for the rocking, boot stomping, country music of artists such as Clint Black, Alan Jackson, and Travis Tritt began to grow within him. Trey began writing songs, playing guitar, and performing in clubs at age 15. He knew early on without a shadow of a doubt that he would make music his career. Trey recorded and released his debut Nashville album entitled “Carolina Man” and was able to work with some of his musical heroes including Brent Mason, Lonnie Wilson and Buddy Hyatt on the album.

Website: https://treycallowaymusic.com/

Instagram: https://www.instagram.com/treycallowaymusic/

Facebook: https://www.facebook.com/treycallowaymusic/

YouTube: https://www.youtube.com/user/TreyCalloway1

TikTok: https://www.tiktok.com/@treycallowaymusic

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You ever get into one of those conversations where you think you know the subject… and then suddenly you’re ten layers deeper than you ever expected to go? That’s what happened here.

This week on Here’s What We Know, we’re joined by Danny Johnson, a stand-up comedian making his mark in the world of clean comedy. We start by talking about the craft, how a joke is built, why timing matters more than the words, and how comedians actually think.

And then we keep going, because comedy is more than just about being funny anymore.

Now it’s social media, followers, clips, going viral, and pressure. The conversation gets more and more fascinating, as one question keeps coming up: If being funny isn’t enough anymore… then what is?

In This Episode:

• The rise of clean comedy and why it’s finding a bigger audience
• How comedians actually write and build material
• The pressure of social media and why it changes everything
• The difference between being funny and being successful
• What it really means to “make it” in comedy today
• And why some of the funniest people you’ve ever seen might still be figuring it out

This episode is sponsored by:

Sterling Oak Cabinetry (Be sure to tell them Gary sent you!)

Bio:

Danny Johnson delivers clean stand-up with "Northeast sarcasm and Southern charm," making him a favorite for theaters, corporate events, churches, and community audiences nationwide. A Dry Bar Comedy featured comedian (Apple TV, Amazon & Peacock), he has appeared on Comedy Central, NateLand Live at Zanies, and shared stages with Howie Mandel, Bob Saget, and many others. A Carnival Cruise Line Comedy Challenge winner and 15-year headliner, Danny blends sharp observations, expressive physical comedy, and relatable stories into a show audiences trust and event planners rebook.

Website: https://dannyjohnson.com/

Facebook: https://www.facebook.com/DannyJohnsonComedy

Instagram: https://www.instagram.com/dannyjohnsoncomedy/

YouTube: https://www.youtube.com/comediandanny

TikTok: https://www.tiktok.com/@dannyjohnsoncomedy

Connect with Gary:

• Gary's Website
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Thank you for listening. Let us know what you think about this episode. Leave us a review!

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There’s what people see on stage, and then there’s everything else.

This week on Here’s What We Know, we welcome back Jerry Flowers, a seasoned bassist, an accomplished songwriter, and music industry veteran, best known for his longtime role as Keith Urban’s bass player and bandleader.

We’ll talk about what life on tour is really like, from playing in front of 80,000 people at major concerts to walking into a room of 50 where no one knows who you are. It’s a side of the music industry most people never see.

Jerry shares what it takes to connect with a live audience, why some artists succeed while others struggle, and how the best performers learn to win over any crowd, whether it’s a stadium or a small private event.

We also get into the realities of touring as a musician, the highs and lows of the road, and the difference between the spotlight and the moments that happen behind the scenes.

This is a conversation about stories. The ones you remember, the ones that shape you, and the ones that don’t seem important at the time… until years later, when you realize they meant everything.

In This Episode:

• What Life on Tour Is Really Like
• Jerry Flowers on Touring with Keith Urban
• The Best Concert Experience: 80,000 Fans in Quebec City
• The Reality of Life After a Big Show
• From Stadiums to Small Rooms: The Truth About Touring
• How Great Artists Win Over Any Crowd
• Early Days on Tour: Bars, Vans, and the Grind
• Learning Storytelling as a Songwriter and Performer
• Music Industry Stories: Jack Black, Hugh Jackman, and More
• Why Storytelling Matters in Music and Life
• Florida Georgia Line, Jason Aldean, and Artist Development
• American Idol vs Real-World Experience in Music
• Why Some Artists Make It and Others Don’t
• Great Songs That Never Became Hits
• The Stories You Carry With You

This episode is sponsored by:

Mike Counsil Plumbing & Rooter (Use code “Gary” to get $89 off any service!)

License #: 679261

Bio:

Jerry Flowers is a seasoned bassist, songwriter, and music industry veteran, best known for his longtime role as Keith Urban’s bass player and band leader. With a career spanning decades, Jerry has toured the world, shared the stage with music legends, and played a pivotal role in crafting chart-topping hits both on and off the road.

Originally from Pinch, West Virginia, Jerry’s musical journey began at just 12 years old, fueled by a passion for bass guitar. His talent and dedication took him from small-town gigs to global stages, touring with The Chicks, Counting Crows, and more.

Beyond performing, Jerry is an accomplished songwriter, earning #1 hits with Billy Currington, Jason Aldean, Sam Hunt, and Ryan Hurd. His musicality and creativity continue to inspire every session he’s in, making him a sought-after collaborator in Nashville’s thriving music scene.

Instagram: https://www.instagram.com/jerryflowersmusic/

Connect with Gary:

• Gary's Website
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Thank you for listening. Let us know what you think about this episode. Leave us a review!