Early Wins: Apparel and Gym Ventures

In this high-energy episode, Charles sits down with Kris Dehnert—founder of Dehnert Media Group and the driving force behind Dugout Mugs—to unpack how creativity, resilience, and systems thinking can turn simple ideas into multi-million-dollar brands.

Kris shares the origin story of Dugout Mugs, where a concept sketched in a kitchen grew into $55M in sales, MLB licensing deals, and a brand loved by fans, athletes, and corporations alike. He breaks down the lessons from his entrepreneurial journey—from early wins in print-on-demand apparel to painful setbacks in restaurants, cannabis, and crypto—and why he believes you fail your way to lasting success.

Together, Charles and Kris dive deep into the mechanics of building lean but powerful organizations: how to scale with small teams, empower people through ownership, and leverage AI and systems to multiply output without multiplying overhead. Kris also reveals his personal philosophy—why fun, family, and reflection matter just as much as profit, and why firing yourself from the process is the real key to freedom.

This isn’t just a story about baseball mugs. It’s a masterclass in turning setbacks into systems, ordinary products into extraordinary brands, and entrepreneurship into a life you actually want to live.

KEY TAKEAWAYS: -How Kris turned a simple idea—baseball bats turned into mugs—into a $55M brand with MLB licensing deals -Why failure in industries like restaurants, cannabis, and crypto taught him the resilience to build lasting businesses -The importance of systems and small, empowered teams to scale without unnecessary overhead -How “firing yourself” from the process creates freedom and long-term sustainability

Head over to provenpodcast.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode.

KEY POINTS: 01:22 – From idea to $55M brand: Kris shares how a simple sketch of a baseball bat mug turned into Dugout Mugs with MLB licensing and millions in sales—while Charles highlights the power of turning passion into product. 05:10 – Failing forward through industries: Kris opens up about losses in restaurants, cannabis, and crypto—and why failure became the tuition that prepared him for future wins. 08:48 – Scaling with small teams: Kris explains how lean operations and empowered people drive efficiency—while Charles reflects on why bigger isn’t always better. 12:30 – Firing yourself from the process: Kris discusses the art of stepping back, creating systems, and letting others take ownership—while Charles points out how this unlocks freedom for founders. 16:42 – Building brands with fun and family: Kris reveals why joy, reflection, and relationships matter as much as revenue—while Charles ties it back to building businesses worth living for. 20:25 – Leveraging AI and automation: Kris shares how AI and systems amplify impact without ballooning costs—while Charles notes how smart tech creates real leverage for entrepreneurs. 25:55 – Redefining entrepreneurship: Kris closes with his philosophy: entrepreneurship isn’t just about profit—it’s about lessons, ownership, and creating brands that people love—while Charles emphasizes the legacy of building with purpose.

Exclusively for Proven Podcast Listeners:

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