Deep Ish

This week on Deep Ish, Jake sits down with country artist & songwriter, Onoleigh.

From leaving a career as a middle school guidance counselor to chasing music in Nashville, Onoleigh opens up about betting on herself, dealing with self-doubt, entrepreneurship, authenticity, burnout, creativity, and learning to build a life that actually feels like your own.

The conversation goes far beyond music. It's about finding purpose, embracing uncertainty, and realizing success isn't always what everyone else thinks it is.

Sometimes it's deep. Sometimes it's just ish.

Brought to you by  ⁨@GrnHausMedia⁩ 

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In this episode of Deep Ish, Jake sits down with hip-hop artist, Nate Rose. Nate has built a career in hip-hop, but success wasn't the destination he thought it would be. Nate opens up about his journey through ambition, ego, faith, philosophy, creativity, and the lessons that reshaped his life.

We talk about making art that reflects who you are, why success alone never satisfies, the evolution of his music, Christianity, regret, purpose, and what it really means to grow.Whether you're an artist, entrepreneur, creator, or simply trying to figure out your next chapter, this conversation will challenge the way you think about success and fulfillment.Brought to you by GrnHaus MediaFollow Nate:https://www.instagram.com/naterosemusichttps://www.tiktok.com/@naterosemusichttps://www.fvr.fan/naterosemusichttps://www.youtube.com/@UC1SC7EbBSWxyzubmgnOcB2A Follow Deep Ish:https://www.instagram.com/deep.ishpodcast/https://www.tiktok.com/@deep.ishpodcasthttps://www.facebook.com/profile.php?id=61577977080176Follow Jake:https://www.instagram.com/jdotlawhttps://www.tiktok.com/@jdotlawhttps://x.com/jdotlawhttps://www.facebook.com/jdotlaw

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 I hope we’ll both be able to look back on years from now.

If you’re a parent, you might relate. If you’re not, I think you’ll still be reminded how refreshing it is to hear the world through the eyes of an eight-year-old.

If you enjoyed this episode, be sure to subscribe, leave a review, and let us know who you’d like to see on a future episode of Deep Ish.

Brought to you by GrnHaus Media.

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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 dive into ADHD, marriage, long-distance relationships, nostalgia, Christmas movies, sports obsessions, and why adulthood feels like everyone is just figuring it out as they go.Brought to you by GrnHaus MediaFollow Karissa:https://www.instagram.com/karissaellamusichttps://www.tiktok.com/@karissaellamusichttps://ffm.bio/karissa-ellahttps://youtube.com/@KarissaEllahttps://www.karissaella.comFollow Deep Ish:https://www.instagram.com/deep.ishpodcast/https://www.tiktok.com/@deep.ishpodcasthttps://www.facebook.com/profile.php?id=61577977080176Follow Jake:https://www.instagram.com/jdotlawhttps://www.tiktok.com/@jdotlawhttps://x.com/jdotlawhttps://www.facebook.com/jdotla

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 life to chase something bigger, how a devastating miscarriage changed his perspective forever, and what it's like raising two boys while building a business from the ground up.

Brought to you by GrnHaus Media

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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 living a lot of life.

The conversation dives into how technology has changed generations, why time seems to move faster as we get older, what really matters in marriage, parenting, and friendship, and the simple philosophy Mark lives by every day: Live. Laugh. Love.

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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's a choice.He also talks about parenting, loss, gratitude, summer traditions, High School Musical 2, Florida Georgia Line, and a few of his favorite summer songs.Brought to you by GrnHaus Media

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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 way, we talk about showing up for people when life gets hard, why "What can I do for you?" matters more than "Let me know if you need anything," and how the people who stay present can change everything.

Brought to you by GrnHaus Media

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Listen to Jon's music:

https://open.spotify.com/artist/3MKuZm9eAVMdw9ni14mzCP

https://music.apple.com/us/artist/jon-mullins/1080469011

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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

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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