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Trying Not To Die: Daily Summaries Delivered
by Jack Osbourne
Trying Not to Die is a bi-weekly video podcast hosted by Jack Osbourne and Ryan Drexler, where caffeine meets chaos and survival is the point. Expect unfiltered conversations, high-performance hot takes, and deep dives into aging, recovery, wellness, mental performance and everything we're doing to cheat death (or at least slow it down). From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud.
Latest Episodes
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- 1 weeks ago57 min
The Paranormal, Ego & Psychedelics | Jack Osbourne and Keith Crossley
In this episode of Trying Not to Die, Jack Osbourne sits down with relationship coach Keith Crossley for a powerful conversation about the unconscious patterns that shape our lives and why so many people struggle to break free from fear, anxiety, and self-sabotage. Keith shares the personal journey that led him to rethink everything he believed about healing, offering a framework for understanding the ego, trauma, and the root causes behind emotional suffering. Together they explore meditation, spirituality, relationships, grief, consciousness, and the mindset shifts that can lead to lasting personal transformation. Thank you to our sponsors: - Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. - If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: https://learn.nocd.com/trying - Get up to $200 off Square hardware when you sign up at square.com/go/trying! #squarepod #ad
- 3 weeks ago1h 0m
Billy Bush On Losing Everything and Starting Over
In this episode of Trying Not to Die, Jack Osbourne sits down with Billy Bush for a brutally honest conversation about public failure, redemption, and rebuilding a life after everything changes overnight. Billy opens up about the fallout from 2016, what he learned from becoming the center of a global media firestorm, and how that experience reshaped his perspective on success, forgiveness, and happiness. The conversation also explores addiction recovery, psychedelics, podcasting, the modern media landscape, and the importance of staying true to yourself when the world has already decided who you are.
- Jun 23, 202632 min
My Wife and I Respond To Our Date At The White House UFC Fight & Why We Went | Jack & Aree Osbourne
In this episode of Trying Not to Die, Jack Osbourne and his wife Aree break down their experience attending the highly talked about UFC event at the White House and the unexpected backlash that followed. They share what it was actually like behind the scenes, from the atmosphere and security to the celebrities, athletes, and unforgettable moments that made the night feel surreal. The conversation dives into the online reaction they received afterward, why they chose to attend, and how quickly people can jump to conclusions based on a single photo or headline.
- Jun 9, 20261h 6m
What Hollywood Doesn't Want You to Notice | Conrad Flynn
In this episode of Trying Not to Die, Jack Osbourne sits down with Conrad Flynn for a fascinating conversation that explores the hidden connections between Hollywood, rock music, Silicon Valley, spirituality, and American culture. Drawing from years of research and personal experiences growing up around the entertainment industry, Conrad shares stories that challenge conventional narratives and reveal unexpected links between some of the most influential people, movements, and moments of the last century. From old Hollywood legends and the counterculture era to technology, faith, and the nature of coincidence itself, this episode is a deep dive into the stories behind the stories and the forces that continue to shape the modern world.
- May 26, 202659 min
Paris Jackson On Grief, Music & Growing Up In The Spotlight
In this episode of Trying Not to Die, Jack Osbourne sits down with Paris Jackson for a raw and deeply personal conversation about grief, identity, addiction, mental health, and growing up under unimaginable public scrutiny. Paris opens up about the pressure of carrying one of the most famous last names in the world, the challenges of finding herself outside public perception, and the ongoing process of healing through music, spirituality, creativity, and recovery. From childhood memories and personal loss to self-acceptance and rebuilding her life on her own terms, this episode explores what it means to survive while learning how to truly live.
- May 12, 20261h 33m
Cory Richards On Climbing Everest and Losing Control
In this episode of Trying Not to Die, Jack Osbourne sits down with legendary climber and photographer Cory Richards for a raw conversation about survival, addiction, trauma, and identity. Cory opens up about bipolar disorder, near-death experiences, chasing purpose through extreme adventure, and the emotional crash that followed some of the biggest accomplishments of his life, including summiting Everest. From avalanches and fame to recovery and rebuilding himself off the mountain, this episode explores what happens when surviving the impossible still isn't enough to save you. Thank you to our sponsors: - Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. -Get up to 39% off your Mitopure Gummies at Timeline.com/TRYING -Go to AquaTru.com now for 20% off (your purifier) using promo code TRYING Music by Ryan Hahn.
- Apr 28, 20261h 7m
Howie Mandel Talks OCD and Conspiracy Theories
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with the legendary Howie Mandel for one of the most honest and eye-opening conversations yet. Howie opens up about living with OCD, anxiety, and intrusive thoughts, and what it's really like inside his mind. From debilitating panic attacks to years of hiding his diagnosis, he shares how a moment on radio changed everything and helped him realize he wasn't alone. The conversation dives deep into mental health, fear, and the reality of coping with something that doesn't just "go away." Howie explains the difference between everyday habits and true OCD, and why understanding that distinction matters more than people think. Along the way, the conversation touches on growing up without mental health awareness, coping with germophobia, raising kids with similar struggles, and the importance of removing the stigma around mental health. Howie offers a powerful perspective on fear. Not as something to avoid, but as the very force that drives people forward in life. Thank you to our sponsors: -Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. -Start your new morning ritual & get up to 43% off your @MUDWTR with code TRYING at mudwtr.com/TRYING! #mudwtrpod #ad
- Apr 14, 20261h 42m
Jim Norton Gets Real: Sobriety at 18, Self-Doubt & Comedy
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with comedian and longtime friend Jim Norton for one of the most brutally honest conversations yet. Jim opens up about getting sober at just 18 years old, why he still struggles with self-worth decades later, and how shame, addiction, and impulse control have shaped his life both on and off stage. From sex addiction and dopamine-driven habits to the reality of long-term recovery, this is a raw, unfiltered look at what it actually means to "work on yourself." The conversation dives deep into relationships, communication, and the damage that can come from saying things you can't take back, as well as the discipline it takes to stop yourself in the moment. Jim also shares his thoughts on confidence, comedy, and why he's never fully believed in his own success despite a massive career. Presented by Caveman Coffee https://www.DRINKCAVEMAN.COM ☕. Powered by Osbourne Media.
About Trying Not To Die
Trying Not to Die is a bi-weekly video podcast hosted by Jack Osbourne and Ryan Drexler, where caffeine meets chaos and survival is the point. Expect unfiltered conversations, high-performance hot takes, and deep dives into aging, recovery, wellness, mental performance and everything we're doing to cheat death (or at least slow it down). From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud.
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