$55 Million with only 5 employees - Kris Dehnert

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About this episode

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…