On Purpose with Jay Shetty

Episode: ALEX WARREN: The Hidden Battles Behind His Historic Rise – Overcoming Self-Doubt, Healing Childhood Wounds & Learning to Finally Feel Enough
Date: December 19, 2025
Guest: Alex Warren (Grammy-nominated singer-songwriter)

Episode Overview

In this moving and deeply candid episode, Jay Shetty sits down with Alex Warren, Grammy-nominated artist whose chart-topping music is matched only by the power and pain of his backstory. Together, they explore Alex's journey through childhood trauma, parental loss, homelessness, personal growth, and ultimately learning to forgive and accept himself. The episode is a testament to resilience, vulnerability, and the healing power of art.

Key Discussion Points & Insights

1. Childhood Trauma & Family Dynamics

• Losing His Father:
  Alex describes his father as his hero, a man who woke up at 5am daily to create joyful, spontaneous memories despite battling cancer. His father’s death at Alex’s age of 9 left an enduring void.
  • "He died when I was nine. I remember when he died, I was doing the stereotypical, 'Wake up, wake up.'" (08:40, Alex)
• Mother’s Addiction & Household Turmoil:
  Following his father's death, Alex’s mother struggled with alcoholism, often leaving Alex and his siblings to raise themselves.
  • "My mom was an alcoholic who wasn't present. So I realized I was raising myself... all of me and my siblings were raising each other." (10:59, Alex)

2. Processing Loss and Grief

• Alex details the surreal, blurred lines between understanding and denial after his father's death, and how he only truly processed the absence years later.
• He also describes the loneliness and trauma of watching both parents die and how it still shapes his worldview.

3. Siblings & the Struggle for Normalcy

• Despite periods of estrangement, Alex and his siblings reconnected as adults, struggling to build a traditional sibling relationship after years of parenting each other.
  • "We rekindled not too long ago... and we try our best to hash that out. It's been nice. I'm really close with all them now." (13:06, Alex)

4. Art as Healing: Music in Trauma and Triumph

• Music as an Anchor:
  Alex’s father introduced him to music, buying him his first guitar. After his father's death, Alex clung to music even as his mother dismissed his dream.
  • “I tried for my entire childhood, and no one cared. I grew up in an abusive household, and when you find something you like, you get torn down for it.” (17:52, Alex)
• Imposter Syndrome and Sincerity:
  Every song written is rooted in authentic emotion, often about love and loss, making criticism particularly piercing.
  • “It’s so strange not to take that personally… These songs helped me through all those things I’m talking about.” (31:29, Alex)

5. Homelessness, Danger, and Forgiveness

• Kicked out at 17, Alex navigated homelessness—sleeping in cars, relying on friends.
• In a shocking accident, Alex was shot by a friend’s dad with a hunting rifle:
  • “It missed my heart by a few centimeters, and it’s stuck in my lung today.” (02:11, Alex)
  • “He officiated my wedding. Huge part of my life, actually. He was a father figure to me... I’m also probably the most forgiving person you’ll ever meet.” (57:03, Alex)
• This event, ironically, brought more father figures and support into Alex's life.

6. Forgiveness of His Parents—And Himself

• His Mother:
  Alex grapples with forgiving his mother, acknowledging her pain and the impossibility of expecting perfection.
  • "My mom watched her husband die and then had to raise four kids by herself. How am I supposed to judge someone like that?" (27:08, Alex)
• Working toward self-forgiveness:
  • Jay: “It’s beautiful that you have the capacity for that for her.”
  • Alex: “I don’t think so. I haven’t thought about it until now, which is funny in such a public setting...” (29:19, Alex)

7. The Importance of Ambition and Faith

• Despite criticism and discouragement ("Give up" – his mom's words), Alex never let go of his ambition, attributing his perseverance to a gut feeling and faith.
  • "For the longest time, I had this gut feeling since I was a kid... I credit that to God. I’m a Christian, and I have faith in that way." (39:00, Alex)

8. Love, Relationships, and Choosing Family

• Meeting His Wife, Kouvr:
  Their relationship started after she learned he was homeless; she left college and moved in with him.
  • “A single girl who would find out that I'm homeless and go, 'Cool, let's do it.' ...She had 500 bucks saved up. She found out I was sleeping in a car and was immediately like, 'Alright, cool. Let's do it.'” (71:04, Alex)
• Alex reflects on past relationships, attachment, learning to accept love, and breaking cycles of trauma.

9. Fame, Insecurity, and Hateful Comments

• Despite success, Alex remains sensitive to criticism due to deep-rooted insecurity and childhood wounds.
  • “I care so much if I have a thousand comments and one of them is someone saying I suck, I walk around all day asking people if I suck...” (84:20, Alex)
• Jay encourages Alex to receive and internalize positive feedback as fully as he does the negative.

10. Fatherhood, Legacy, and the Power of Story

• Alex keeps his father's memory alive through storytelling and home videos, intending to do the same for his future children.
  • "People die twice: when they die, and when you stop telling their story. My whole goal... is just to keep him alive." (50:53, Alex)
• His greatest goal is to be remembered as a good father.

Notable Quotes & Memorable Moments

• "I often hear about my dad, and I've put him on this pedestal of just being this perfect guy. I don't want him to be. I want to have mistakes. I want him to have flaws, because I have flaws."
  (48:53, Alex Warren)

• "I battled with depression... I started to think, what was the point? Why did all these things happen to me? Why is this my life and where am I supposed to be?... What's the point of living if you can't constantly try and become a better person?"
  (46:04, Alex Warren)

• "I want someone to say that I was a great father. Say what you want about me, say what you want about my music, but I cared a lot, and I just want to be a good father."
  (48:20, Alex Warren)

• On grief and music:
  "Making music that allows you to articulate that feeling... I've just been really focusing on that."
  (62:17, Alex Warren)

• On forgiveness after his mother’s death:
  "It's closure in some sense... I never got to have that conversation. I didn't talk to my mom for a long time. Yeah, it's hard."
  (27:06, Alex Warren)

• Final Five: Best and Worst Advice

  • “Everything happens for a reason.” (94:07, Alex)
  • Worst advice: “Give up.” (from his mom) (94:20, Alex)

• Leaving a message for his future children:
  "Hey kids. It's your dad... I just want you to know that I love you so much, and I pretty much talked about you this entire podcast..."
  (95:01, Alex Warren)

Timestamps of Key Segments

• Alex’s Early Trauma and Losing His Dad – 02:11, 05:45, 08:16, 08:40
• Family Reconnection and Sibling Dynamics – 12:49, 13:06
• Art, Music, and Criticism – 17:52, 18:15, 31:29
• Processing Mother’s Addiction and Death – 19:33, 22:28, 25:14
• Forgiving His Parents & Himself – 27:06, 29:19, 37:33
• Faith and Perseverance – 39:00, 41:16
• Homelessness and Getting Shot – 53:28, 55:37, 57:03
• Love and Meeting Kouvr – 71:04, 72:31
• Struggles of Fame & Insecurity – 84:20, 85:43, 86:39
• Fatherhood and Legacy – 48:20, 50:53, 95:01

Tone and Language

The episode is peppered with raw honesty, humor, self-deprecation, and warmth. Jay provides a safe, compassionate space, with Alex meeting vulnerability with authenticity—never shying from the darkness of his experiences, but also highlighting hope, forgiveness, and personal growth.

Final Reflections

This episode stands as a masterclass in resilience and honesty. Alex Warren’s willingness to examine his wounds, forgive others and himself, and channel pain into beauty offers both comfort and inspiration. Jay Shetty’s skillful, empathetic questioning guides the conversation to profound places—making this a deeply relatable and uplifting listen for anyone who has ever felt “not enough” or struggled to overcome their past.

For listeners looking for healing, purpose, or simply a reminder that one can survive, overcome, and even thrive after hardship—this is an essential episode.