Deep Ish

In this episode of Deep Ish, Jake sits down with Zotz, a music industry veteran, entrepreneur, and founder of Rocketship — a platform using AI and music data to help artists understand their potential audience and market their music more effectively. We get into the wild journey from working with artists and building college music tours to launching businesses, learning from failure, and creating...

On this episode of Deep Ish, Jake sits down with country singer-songwriter Jenny Tolman to talk about the person behind the music. From the highs of early career success to the uncertainty that followed COVID, Jenny opens up about navigating the Nashville music industry while building a family and refusing to give up on the career she's always wanted. We get into the pressure to constantly rel...

In this episode of Deep Ish, Jake sits down with TJ Wilt, a Nashville native, entrepreneur, father, and architect, to talk about the unexpected turns that shape our lives and the courage it takes to start a new chapter. TJ shares stories from his years in business, including his time with Nashville institution Cumberland Transit and the coffee shop he helped build, before opening up about a major...

In this episode of Deep Ish, Jake sits down with former Alabama wide receiver & college football national champion, Mac Hereford. Mac spent his childhood dreaming about playing football at Alabama. Mac and Jake go far beyond football. They talk about the cost of chasing a dream, the danger of letting accomplishments become your identity, competition, faith, family, failure, finding your next d...

In this week's episode of Deep Ish, Jake sits down with country singer songwriter Christan Parker. We talk about the strange intersection between law and creativity, how becoming a lawyer actually changed the way Christian thinks, and what happens when that analytical brain collides with songwriting. Christian also opens up about moving to Nashville, building an independent music career, being tol...

This week on Deep Ish, Clay Barker joins Jake to talk about his unconventional path into music — from playing drums in Christian metal bands and nearly pursuing physical therapy school to becoming a Nashville songwriter and country artist. Clay opens up about moving to Nashville, navigating the uncertainty of COVID, learning how to write alongside hit songwriters, and the years it took to find a s...

In this week's episode of Deep Ish, Jake sits down with business owner, podcast host & producer, Alex Lagos. Alex has spent years behind some of the biggest conversations in podcasting, producing shows like Bussin’ With The Boys, Just Being Ernest, Net Positive, and more, and building his own company, Lagos Creative. But this conversation goes way beyond how to make a podcast grow. Alex br...

This week on Deep Ish, Jake sits down with singer-songwriter and former professional baseball player Bryan Ruby for a conversation about baseball, music, Nashville, taking risks, and knowing when it's time to turn the page. Bryan spent nearly two decades playing baseball, eventually playing professionally and continuing to pursue the game long after college. But while baseball was still his ca...

In this episode, Jake sits down with Carolyn Miller. Carolyn spent her childhood on stages in New York — acting, singing, Broadway, TV, commercials, and voiceover work. By all accounts, she was already on the path she had dreamed about since she was a kid. Then, in her late 20s, everything changed. After years of pursuing acting, Carolyn had a realization that Nashville — and country music — was w...

In this week's episode of Deep Ish, Jake sits down with Ava Claire. Ava has been writing songs since she was eight years old, playing shows around Nashville since she was 11, and somehow found herself auditioning for American Idol at 16. But the wildest part? She says she didn't even realize she was pursuing music until she was already doing it. In this episode, Ava talks about growing up...

In this week's episode of Deep Ish, Jake sits down with Zoe Jean Fowler for a conversation about leaving behind the version of her career she thought she was building, moving to Nashville, finding her voice as a country artist, and learning to trust who she actually is. Zoe opens up about the transition from Christian music into country, the pressure to fit into a particular box, the reality o...

In this episode, Jake sits down with Bonheur Vacations Co-Founder Jodie Kurtz and they dive into what it really looks like to chase purpose over comfort. After 22 years climbing the corporate ladder—including nearly a decade at Google—Jodie made the decision that most people only dream about. She walked away from stability, packed up her family, and moved to Florida to help build something from th...

In this special "poolside" solo edition of Deep Ish, Jake comes to you live (well, recorded live!) from a family vacation along Scenic Highway 30A. Between pool jumps and beach football, Jake reflects on a family tradition that’s lasted since he was five years old and why making time for family trips matters now more than ever. Plus, Jake gets a surprise guest appearance from his son Rom...

This week on Deep Ish, Jake sits down with country artist & winner of season 5 of For Love or Likes on the Outdoor Channel, Becca Bowen to talk about the unexpected road that led her from small-town South Carolina to Nashville.  She went viral catching a 46-pound catfish with her bare hands... but that's only the beginning of the story. From winning a reality TV hunting competition during...

This week on Deep Ish, Jake sits down with country artist & songwriter, Onoleigh. From leaving a career as a middle school guidance counselor to chasing music in Nashville, Onoleigh opens up about betting on herself, dealing with self-doubt, entrepreneurship, authenticity, burnout, creativity, and learning to build a life that actually feels like your own. The conversation goes far beyond music. I...

In this episode of Deep Ish, Jake sits down with hip-hop artist, Nate Rose. Nate has built a career in hip-hop, but success wasn't the destination he thought it would be. Nate opens up about his journey through ambition, ego, faith, philosophy, creativity, and the lessons that reshaped his life. We talk about making art that reflects who you are, why success alone never satisfies, the evolution of...

Kids have a way of reminding us what really matters. In this episode of Deep Ish, Jake sits down with his oldest son, Roman, for his second appearance on the podcast. We talk about becoming a big brother, growing up, football, Dude Perfect, summer adventures, school, family, and the dreams he has for the future. It’s funny, honest, and surprisingly thoughtful. These are the kinds of conversations...

This week on Deep Ish, Jake sits down with Singer-songwriter Karissa Ella, for a conversation that goes way beyond music. From growing up in small-town Ohio to chasing a career in Nashville, Karissa opens up about the fear that comes with pursuing a dream, the importance of having people who believe in you, and why success is earned one step at a time—not overnight. Along the way, Jake and Karissa...

This week on Deep Ish, Jake sits down with one of his closest friends and the founder of Delta Property Solutions, Colton Mosley. What starts as a conversation about moving from small-town Alabama to Nashville turns into a deeper discussion about risk, friendship, marriage, fatherhood, loss, and learning to appreciate the season you're in. Colton shares the story of leaving behind a comfortable li...

This week, Jake sits down with his neighbor and friend, Mark Riley. What started as porch conversations over coffee turned into this conversation of Deep Ish. Mark shares stories from growing up in a family that's called the same Tennessee community home for generations, serving in the Marine Corps, raising a daughter later in life, 33 years of marriage, and the lessons that only come from liv...

This week is a little different. No guest. No interview. Just Jake. As Deep-ish approaches 30 episodes, Jake sat down and reflected on the journey so far, what he's learned through some difficult seasons of life, why healing doesn't always mean "getting over it," and a piece of advice that completely changed the way I think about taking risks:Being ready isn't a feeling—it&#3...

In this episode of Deep Ish, Jake sits down with singer-songwriter Jon Mullins to discuss marriage, long-distance dating, faith, miscarriage, friendship, and the moments that shape us most. Jon shares the story of losing a pregnancy after years of believing they may never have children, the fear of trying again, and how a song written in the middle of the storm carried them through it. Along the w...

This week on Deep Ish, Jake sits down with one of the people who has impacted his life more than almost anyone else — Jackie Brewster. They talk about marriage, heartbreak, healing, identity, therapy, faith, midlife crisis, Enneagram work, raising kids, ministry, career pivots, and what it actually looks like to build a meaningful life over decades. Jackie shares the story behind her journey into...

On this week's episode of Deep Ish, Jake sits down with longtime family friend Whitley Smith. From getting married young and navigating two completely different upbringings to growing through hard seasons together, this episode dives into what marriage actually looks like behind the highlight reel. They talk about the impact divorce can have on your view of relationships, learning how to build you...

In this week's episode of Deep Ish, Jake sits down with one of his oldest friends, Ben Halsey. We talk about everything from growing up at church camp and awkward high school years to marriage, fatherhood, communication, and what it actually takes to build a healthy family over time. Ben shares the story of dating his wife in high school, breaking up in college, finding their way back to each...