Deep Ish

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...

In this week's episode of Deep Ish, Jake sits down with singer-songwriter Sheyna Gee for one of the most honest and unexpectedly hilarious conversations. We get into Sheyna’s journey from growing up in LA to moving to Nashville with no backup plan, betting everything on music, navigating heartbreak, family trauma, ADHD, toxic relationships, and what it really takes to survive as an independent art...

In this episode, Jake sits down with Aaron Dwyer—former police officer, golf pro, and now successful real estate leader. In this episode, we unpack a powerful shift in perspective: You don’t have one “calling” — you have a series of assignments. We dive into identity, purpose, success, and why so many people chase the wrong things for years… only to feel empty when they finally get them. This conv...

In this episode, Jake sits down with country R&B artist Mike Parker. He opens up about leaving a small town in Virginia, taking a leap to LA, and realizing that success without purpose doesn’t hit the way you think it will. We talk about the reality of chasing music in LA, why “having everything” can still leave you unfulfilled, how American Idol changed everything, how he found his sound—and...

In this episode, Jake sits down with Chef Daniel Mangione, Executive Pastry Chef in Nashville, to talk about far more than just desserts. From building tables during COVID to leading a high-level kitchen team, Chef Daniel shares how creativity, discipline, and service all intersect. We get into the chaos of starting over in a new city, the unexpected success of a side hustle that turned into a ful...

In this episode of Deep Ish, Jake sits down with Josh Gamble. This one goes everywhere—in the best way. We start with how we met at Barry’s and quickly realize something wild: same upbringing, same environments… just 10 years apart. From Christian schools and strict rules to sneaking music, stealing golf carts (allegedly), and figuring out who we actually are—this episode is a real look at how per...

In this episode, Jake sits down with David Piersaul. This episode starts unfiltered and turns into one of the realest conversations we’ve had. From how we met to navigating faith, friendship, and creativity, we get into what it actually means to show up for people—and for your work—without faking it. We talk about the difference between empathy and “out-struggling,” why most people settle for good...

In this episode of Deep Ish, Jake sits down with rising country artist Peech. to talk about the turning points that shaped his life—from growing up in a small town, to using music as an emotional outlet, to spending time in jail, and completely redefining his direction. We get into the moment everything shifted for him, why he turned to music instead of talking about his emotions, and how his jour...

March Madness is here—and we’re breaking it all down in a special edition of Deep Ish. From bracket chaos and bold predictions to the most painful heartbreaks we’ve ever experienced as fans, this episode is packed with everything that makes college basketball special. We debate whether the first two days of March Madness are the greatest in sports, talk Cinderella runs, relive brutal losses, and g...

In this episode of Deep Ish, Jake sits down with arguably his favorite guest he'll ever have… his oldest son Roman. They talk about school, sports, friendship, becoming a big brother, his dreams of meeting the guys from Dude Perfect, and some hilarious “Would You Rather” questions. Somehow the conversation moves from hockey at recess… to Duke basketball… to whether Jake's homemade pizza be...

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...

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...

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...

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...

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. Brought to you by GrnHaus Media

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 p...

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. Brought to you by GrnHaus Media