In this episode of Deep Ish, I sit down with one of my closest friends, Josh Hill — attorney, podcast host, and husband — for a conversation that’s equal parts hilarious, reflective, and unexpectedly meaningful.

We tell the full story of the trip to East Tennessee, where everything went sideways: wrong turns down a mountain, missing license plates, no wallet, a handgun in the car, and a state trooper who thankfully decided not to pull us over. It was the day we thought we might go to jail… or worse — and the day our friendship was cemented forever.

From there, we talk about what it means to be unapologetically yourself, how marriage actually works when you stop trying to change your partner, raising kids in a digital world, and why the people who know you best are the ones who help you become better — not different.

Brought to you by GrnHaus Media

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

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.

Brought to you by GrnHaus Media