Jackie Brewster | We Didn’t Throw in the Towel

Jackie Brewster | We Didn’t Throw in the Towel

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 Enneagram coaching, the hard seasons she and her husband walked through behind the scenes, and why growth often starts with brutal self-awareness.Brought to you by GrnHaus Media Follow Jackie: https://enneagramwithjb.com/ https://www.instagram.com/enneagramwithjb/ Enneagram with JB Podcast: https://www.buzzsprout.com/2075863 Follow 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

Whitley Smith | This Wasn't in the Vows

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 your own family culture, and why the right partner can completely change the trajectory of your life. Along the way, they also get into Nashville food spots, beach obsessions, parenting, social media brain rot, growing up in the 90s, real estate, nursing, and the kind of friendship that picks right back up after years.Brought to you by GrnHaus MediaFollow Deep Ish:https://www.instagram.com/deep.ishpodcast/https://www.tiktok.com/@deep.ishpodcast?is_from_webapp=1&sender_device=pchttps://www.facebook.com/profile.php?id=61577977080176

Ben Halsey | The House Is Clean

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.

Sheyna Gee | I Got Fired From Chili’s

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  [https://studio.youtube.com/channel/UCbJDx-RB82mY7aEPAoWGrSQ] 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

Aaron Dwyer | You're Not Behind

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