Jack Osbourne first became famous on early 2000s reality television as a quick-witted teen navigating the chaos of unconventional family life as the son of rock legend Ozzy Osbourne. Years after his time on MTV’s The Osbournes, Jack transformed his high-profile exposure into a foundation for serious business. His career evolved significantly: He moved behind the camera to produce, then transitioned back into the spotlight to host a slew of travel and paranormal shows, including the related podcast, Ghosts and Grit with Jack Osbourne. Beyond hosting, Osbourne has also produced documentaries about his father and briefly ran his own production company, Osbourne Media House. Most recently, he’s launched the podcast Trying Not to Die and co-owns beverage brand Caveman Coffee.
The Value of Failure
His disciplined focus has sustained him through several ventures. He’s learned that true success requires an internal barometer that doesn’t rely on external validation but on a sense of profound purpose. He notes that many high-profile CEOs often boast about their varied successes. “I’m more curious in people’s failures because that’s how you course correct. And I don’t think you hear enough people talking about that,” he says. “For everything I’ve been successful at career-wise, there’s probably anywhere from three to five failures in between those successes.”
Mastering High-Performance Living
That same curiosity now fuels his latest project, Trying Not to Die, where the conversation is just as much about mental endurance as physical health. Osbourne, who was diagnosed in 2012 at age 26 with relapsing-remitting multiple sclerosis and is open about spreading awareness, co-hosts the show with his longtime friend, Ryan Drexler, a jujitsu athlete and entrepreneur. Together, they explore the real meaning of mastering the art of high-performance living, enduring strength, and retaining a rebellious edge past 30. Featuring a diverse range of guests—from competitive athletes and health junkies to musicians and artists—the show is anything but a traditional self-help guide. Instead, Trying Not to Die is an honest exploration where the hosts and their guests openly tackle the unspoken realities of aging and sustained performance.
Drexler says that he and Osbourne’s mutual love of physical fitness and being healthier for their families inspired the show. “I get to work with my best friend, and explore our guests, and enjoy our company, and we work really well together,” Drexler says. One of his favorite aspects of the process is interviewing people and uncovering details about their guests that the public would otherwise never learn.
Osbourne wants the podcast to feel like an irresistible overheard conversation. “Have you ever sat in a coffee shop and just been kind of minding your own business, but then you hear a good conversation going on?” Osbourne asks. “I want people who are listening to feel like they want to participate.”
The Business of Wellness
Beyond the microphone, Osbourne, in keeping with his health journey, is now a co-owner of Caveman Coffee Co., a beverage brand focused on producing “clean energy” coffee for the health-forward market. The brand is known for its nitrogen-charged cold brew, which contains no sugar or additives and is specifically designed to alleviate the typical crash that comes after consuming coffee. “Our Nitro Cold Brew is literally just coffee and water,” he says, adding that more new products are in the works, such as a protein-infused latte and an Arnold Palmer.
The Emotional Weight of Responsibility
When asked about the lesser-known difficulties of running a business, he described the constant tension he faced spearheading a production company: striving to treat his employees well and ensuring they were compensated fairly. However, he acknowledged the challenging emotional dance required to keep the company afloat. At times, this necessitated making difficult—even “ruthless”—decisions to save the business, recognizing that without the company, there was no employment. He struggled to maintain this survival instinct without making himself feel evil during lean times.
“I don’t think you hear enough people actually talking about the emotional weight of that responsibility,” he says.
Success Defined By Inner Peace
Despite building a wide-ranging portfolio from television to podcasts and coffee ventures, his definition of success isn’t what you might think. He says it looks different to him. “I think there’s this notion… that you gauge success on how happy you are,” he says, immediately challenging the idea. “I think that’s a big misconception, right? Because happiness is such a fleeting [and] temporary thing. It’s not a sustainable state. You don’t see people walking around 24/7 just happy.”
His compass, instead, points toward a profound sense of inner stillness.
“Not to get too hippie, but how much inner peace was obtained through that? Meaning, do I feel comfortable? Do I feel confident? Do I feel like I brought value to this and I gained value from it? And really, ultimately, was it the right thing?”
Resilience: The Quiet Force
He says that resilience is something you can rely on throughout a difficult time. He reflects and asks himself: Have I been in this position before? What did I learn as a result of that? Is that applicable to this exact moment? This intel helps him determine whether to push ahead or let go. “Having resilience, in my opinion, can only be gained through experience. And so having that ability to reflect on the experience, especially in business or work or whatever…, I think resilience is so important.”
His career proves that resilience is not just a personal quality—it’s a necessary tool for course correction, a requirement for lasting commitment and the quiet force that sustains true leadership.
“Experiencing difficulties is the root of resilience,” Osbourne says.
In the end, whether he’s behind a mic or behind a brand, Osbourne’s still doing what he’s always done: “Trying not to die” and inspiring the rest of us to really live.
