Listen: "Troy Eckert | The Bomb Hole Episode 230" from The Bomb Hole podcast.⬇️
Troy Eckert's nearly three-hour conversation on The Bomb Hole (Episode 230, released September 10, 2025) offers something rare: an unfiltered look at what happens when passion projects become billion-dollar businesses, when grassroots movements meet corporate structures, and when success forces you to choose between growth and soul.
As Volcom's first employee and eventual Global VP of Marketing, Troy didn't just witness the explosive growth of one of action sports' most influential brands—he was the architect of its cultural identity across surf, skate, and snow. But this isn't a success story. It's something more valuable: a honest examination of what gets lost in translation when counterculture meets the boardroom.
Building Something That Matters
Troy's early days at Volcom reveal a blueprint that many founders chase but few achieve. Working directly under co-founder Richard "Wooly" Woolcott in the early '90s, the team wasn't following a playbook—they were writing one. The focus wasn't on market analysis or growth projections; it was on creating events, supporting athletes, and building authentic connections with communities who actually lived the lifestyle.
What made Volcom resonate wasn't sophisticated marketing—it was the absence of sophisticated marketing. The brand grew because it understood something fundamental: people can sense when you're part of their world versus trying to sell to their world. Troy and the team weren't manufacturing authenticity; they were living it.
This raises an important question for anyone building something today: How do you scale authenticity?
The Turning Point: When Going Public Changes Everything
The conversation shifts when Troy discusses Volcom's decision to go public. This is where the episode becomes genuinely instructive. Troy doesn't romanticize the early days or villainize the corporate transition—he simply describes how different forces create different outcomes.
Going public brought resources, opportunities, and reach. It also brought shareholders, quarterly expectations, and decision-making frameworks that prioritized different metrics than those that built the brand. Troy's eventual departure wasn't about failure; it was about recognizing when the game you're playing no longer aligns with why you started playing.
For anyone navigating career transitions or building projects, this tension is universal. The skills that make you successful in phase one rarely match what's required in phase two. The question isn't whether change is coming—it's whether you'll recognize when the change requires you to evolve or exit.
The Garden: Creating Something Timeless
One of the episode's most compelling segments explores the creation of The Garden, Volcom's legendary snowboarding film. Troy's detailed account of its production reveals what separates memorable work from disposable content: intention, craft, and genuine respect for your audience.
The Garden wasn't just a marketing asset—it was a contribution to snowboarding culture. The difference matters. When you create something that serves a community rather than just leveraging it, people feel it. That film endures not because it sold products, but because it captured something true about the sport and the people who loved it.
This principle applies far beyond action sports. Whether you're writing, teaching, building products, or leading teams—are you extracting value from your audience or adding value to your field?
Life After the Dream Job
Troy's post-Volcom trajectory offers perhaps the most valuable lessons. Now working as an equanimity coach and involved with Radical Voyage, he's rebuilt his professional life around different priorities: personal boundaries, meaningful work, and the kind of balance that allows him to score "the best waves of his life" at 50+.
His advice—"put yourself first," learn to say "no," focus on internal rather than external turmoil—sounds simple until you consider how many people sacrifice themselves for organizations that won't remember their names. Troy's transition wasn't about finding another dream job; it was about redefining what success actually means.
The transformation from building a billion-dollar brand to coaching individuals through their own transitions might look like a step down from the outside. But Troy's energy in this conversation suggests he's found something more sustainable: work that aligns with who he is rather than who the market needs him to be.
What This Conversation Actually Offers
This isn't just action sports nostalgia—though there's plenty of that for anyone who grew up in the '90s scene. It's a masterclass in navigating the tension between passion and profession, between building something meaningful and maintaining what made it meaningful in the first place.
The real value comes from Troy's willingness to discuss what most successful people won't: the complexity of winning, the cost of growth, and the courage required to walk away when success stops serving you.
For anyone building something, transitioning careers, or questioning whether their current path still makes sense—this conversation offers both validation and practical wisdom. The path forward rarely looks like the path that got you here.
Questions Worth Considering
What would change if you prioritized internal alignment over external achievement?
Where in your career are you holding onto something because of what it represents rather than what it currently offers?
How do you know when it's time to evolve versus exit?
What does success actually mean to you, separate from what it's supposed to mean?
Listen: "Troy Eckert | The Bomb Hole Episode 230" from The Bomb Hole podcast.⬇️
Best for: Anyone navigating career transitions, builders questioning their path, professionals wondering how to maintain authenticity while scaling, or action sports enthusiasts interested in the cultural history of brands that actually mattered
Category: Business & Entrepreneurship / Personal Development
The Bomb Hole is hosted by Chris Grenier, Seth Huot, and SILK, featuring sponsors including Arbor Snowboards, Bubs Naturals, and Yeti. For show notes and rider links, visit thebombhole.com
Exploring Stoicism’s Path to True Wisdom: Ryan Holiday on Modern Wisdom
Listen: Modern Wisdom #1001 - Ryan Holiday: "Stoicism's Lessons on Becoming Wise"⬇️
If you’re into personal growth and ancient philosophy with a modern twist, I’ve got a podcast episode that’ll hit the spot. Episode #1001 of Modern Wisdom, hosted by Chris Williamson, features bestselling author Ryan Holiday diving deep into “Stoicism’s Lessons on Becoming Wise.” It’s a great listen for anyone feeling overwhelmed by life’s chaos.
In this nearly two-hour conversation, Ryan breaks down why being smart isn’t the same as being wise—intelligence might get you ahead, but wisdom keeps you grounded. He shares raw insights from his own near-death experience, highlighting how daily habits like reflection and emotional control compound over time to build real resilience. 0 Drawing from Stoic principles, they explore practical ways to apply these timeless ideas: shedding the illusion of being “smart,” embracing humility, and avoiding the traps of ego and haste. 0
Key takeaways? Wisdom isn’t about knowing everything; it’s about seeing deeper and acting right in the moment. Ryan emphasizes that even the brightest minds falter without it, using historical anecdotes like the Wright Brothers and Admiral Stockdale to drive the point home. 0 If you’re chasing better decision-making or just need a Stoic pep talk, this episode is gold.
Listen: Modern Wisdom #1001 - Ryan Holiday: "Stoicism's Lessons on Becoming Wise"⬇️
P.S. Got a podcast that changed how you think about your career or helped you navigate a major transition? I'm always looking for conversations that offer genuine insight rather than just inspiration. Let me know what's actually helping you grow.
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Happy listening,
Kuba 🎧