Deep Ish

In this episode of Deep Ish, Jake sits down with AJ Thomas, the founder of NAPD, a Nashville-based clothing brand, but his journey started far from entrepreneurship. From growing up in a small Illinois town to playing college football, AJ thought the path was clear — until life forced him to pivot.

In this episode, we talk about identity after sports, the power of relationships, taking risks, and how a few unexpected moments in Nashville helped shape his entire career.

We also dive into faith, family, and why the people you meet along the way might matter more than the plan you started with.

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Dr. Cody Prizer has rehabbed professional athletes, worked alongside heart surgeons, and built a career around helping people move without pain. But in this episode of Deep Ish, we talk about his newest journey — becoming a father.

We dive into what it feels like to go from being the fixer to being the one learning. The pressure of being the “rock” of a household. The reality that success doesn’t prepare you for sleepless nights. And the perspective shift that happens when you realize your parents were figuring it out for the first time, too.

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This week on Deep Ish, Jake sit down with Parker Graye — a small-town Ontario native who grew up on hockey rinks, bush parties, and Tim Hortons runs — and unpack the long road from snowboarding in Banff to building a life in country music.

What started as a restless pull to leave home at 17 turned into a winding journey through broken collarbones, studio houses in Vancouver, 300-song writing years, and a Zoom session that changed everything.We talk about comfort — and why it can quietly trap you.We talk about nostalgia — and how it shapes what we create.

We talk about coffee, Christmas music hot takes, and the courage it takes to pivot when something isn’t working.

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In this episode of Deep Ish, Jake sits down with one of his closest friends, singer-songwriter Halle Kearns, for an honest conversation about the moments that quietly shape who we become.

We talk about growing up in the aftermath of her parents’ divorce, how music became both an escape and a lifeline, and the deeper realization she’s only recently uncovered — that her drive to pursue music may have been rooted in a desire to feel important and heard.

From navigating comparison and success in Nashville, to the hidden emotional weight we carry from childhood, to learning how to separate what we do from who we are — this conversation goes places you don’t usually hear artists go.

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In this episode of Deep Ish, Jake and Tim Clarke touch on adoption, independence, relationships formed in weird seasons of life, and the quiet ways time and experience shape who we become. We talk about the pandemic’s effect on relationships, the loss of character in our world, and the things we don’t realize we’re carrying until someone asks the right question.

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In this episode of Deep Ish, Jake sits down with Trea Allen — creative, former athlete, and founder of the clothing brand On the Other Side — to talk about what happens when you realize you don’t fit the mold you were given.

Trea reflects on growing up in a sports-first world while quietly carrying a love for music, creativity, and self-expression — and the tension that comes with choosing a path that doesn’t make sense to everyone else. Together, they unpack identity, pressure, faith, culture, and the long road from who you were expected to be to who you actually are.

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DEK of Hearts joins Deep Ish to talk about the real journey behind their rapid rise — from small town beginnings and early bar gigs to The Voice and beyond. We discuss choosing Niall as a coach, navigating imposter syndrome, building a band from scratch, staying rooted in faith, and why “overnight success” is almost never actually overnight.

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In this episode of Deep Ish, Jacob sits down with creative entrepreneur and filmmaker Blaine for a wide-ranging conversation about purpose, identity, success, and what it actually means to live a meaningful life.

From growing up in Indiana, being told he’d “never be good enough,” and chasing achievement at a young age — to building a business at 14, walking away from college soccer, and moving to LA with no connections — Blaine shares how early success still left him empty, and what ultimately reframed his definition of fulfillment.

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In Episode 3 Nashville country artist Madeline Carter  joins Deep Ish to talk about songwriting, faith, and the long road to finding your sound. We dive into the grind behind the scenes, chasing purpose over trends, and why success is rarely overnight.

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In this episode of Deep Ish, Jake sits down with one of his closest friends, Kelly — creative, worship leader, designer, entrepreneur, and founder of the Southern-rooted brand Wayne — to talk about burnout, identity, growing up in the 90s, healing, friendship, marriage, and what it means to be yourself when life forces you to change.

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