Deep Ish

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 other, and now raising three boys together. We also get honest about the challenges of parenting, balancing work and creativity with family life, and learning how forgiveness and communication shape a marriage over the long haul.

This episode feels like sitting in on a real conversation between lifelong friends about life, faith, relationships, and becoming the kind of husbands and dads we hope to be.

Follow Ben:

https://www.instagram.com/ben_halsey?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==Listen to Ben's music:

https://open.spotify.com/artist/3f1tvc5EPsB7ZEGwqDjLrJ?si=FLkf5_okTIGEtYcGhAk7PQFollow Deep Ish:

https://www.instagram.com/deep.ishpodcast/

https://www.tiktok.com/@deep.ishpodcast?is_from_webapp=1&sender_device=pc

https://www.facebook.com/profile.php?id=61577977080176

Brought to you by GrnHaus Media.

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 artist in one of the toughest music cities in the world.

This episode is equal parts funny, chaotic, and real—from getting fired from Chili’s for calling someone a bitch… to deep conversations about identity, healing, family, and staying committed to your purpose when life keeps testing you.

Brought to you by GrnHaus Media

Follow Sheyna:

https://www.instagram.com/geeis4gangster/https://linktr.ee/geeis4gangster?utm_source=ig&utm_medium=social&utm_content=link_in_biohttps://www.tiktok.com/ ⁨@geeis4gangster⁩ 

Listen to Sheyna’s music:

https://open.spotify.com/artist/05BcZCAQvpZCJSRqWFzSnF?si=JbTKalajTHmJTazJd1yDLQhttps://music.apple.com/us/artist/sheyna-gee/685081703

Follow Deep Ish:

https://www.instagram.com/deep.ishpodcasthttps://www.tiktok.com/@deep.ishpodcast?is_from_webapp=1&sender_device=pchttps://www.facebook.com/profile.php?id=61577977080176

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 conversation covers why “finding your calling” might be holding you back, how to stop tying your identity to what you do, the real reason successful people still feel unfulfilled, parenting, resilience, and raising kids in a distracted world, and how to build a life that actually feels meaningful.

Brought to you by GrnHaus Media

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 himself—in Nashville, and faith, failure, and figuring it out as you go

This is one of those conversations about trusting your gut, embracing the uncomfortable, and learning that sometimes the path forward starts with starting over.

Brought to you by GrnHaus Media

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 full-blown business, and the lessons learned from doing things the hard way. But more than anything, this is a conversation about leadership—what it looks like to build people up, create space for others to thrive, and find purpose in the process.

Brought to you by GrnHaus Media

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 perspective changes everything.

We talk about:

• Growing up in strict religious environments
• The stuff we used to hide (music, behavior, all of it)
• How culture shifts—and how we judge the past differently now
• Why maturity changes how you see everything
• And how two completely different paths can come from the same foundation

Brought to you by GrnHaus Media

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 enough, and how the small details in life (and art) actually matter more than anyone realizes. This is about doing things right, staying honest with yourself, and not mailing it in when it counts.

Brought to you by GrnHaus Media

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 journey from rap into country helped him find his voice. Peech. also shares how isolation forced him to grow, and the mindset that ultimately changed everything.

Brought to you by GrnHaus Media.

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 give our unfiltered takes on this year’s bracket.

Brought to you by GrnHaus Media

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 beats Domino’s.

It’s funny, honest, and a reminder that kids often see life in the simplest and most meaningful way. This might be the most special episode we’ve done yet.

Brought to you by GrnHaus Media