Trying Not To Die

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. Powered by Cave Man Coffee.

Episodes

September 9, 2025 54 mins

Sean Avery joins Jack Osbourne and Ryan Drexler on the Trying Not To Die Podcast to talk hockey brawls, New York chaos, and his unexpected role as a romance novelist. From NHL fights and celebrity encounters to Vogue internships and jiu-jitsu training, Avery proves why he’s the ultimate cultured barbarian.

Presented by Caveman Coffee www.CAVEMANCOFFE.COM ☕. Powered by Osbourne Media.

Watch more from Jack:

👻 The Most Haunted ⮕ http...

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Celebrity surgeon Dr. Jason Diamond joins the show to talk immortality science, plastic surgery for men, and why your muscle tissue might be the key to not dying ugly.

We get into club trauma, Celsius addiction, the science of aging, and whether lifting weights is better than injecting your face. Also: 80s cars, strange bets, and the IROC-Z camera incident.

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n the debut episode of Trying Not To Die, Navy SEAL and discipline king Jocko Willink drops in for a wildly unpredictable conversation about Jiu jitsu, drone warfare, modern masculinity, and his deep love for Black Sabbath.

We talk about why war is now content creation, what it takes to stay calm in chaos, and how Jocko got completely starstruck meeting

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June 28, 2025 55 secs

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...

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