Stephen Berg’s journey reads like a crash course in perseverance. Growing up in Evergreen, CO, with a pilot father, his childhood was shaped by curiosity, travel, and an early fascination with aviation. After 9/11, that dream dissolved — both because of his opposition to the war and witnessing his father lose his pension when United Airlines filed bankruptcy. The experience planted two lifelong seeds: distrust in corporate systems and an obsession with independence.

He tried it all - flipping houses, running a wine department, even becoming a certified sommelier and assistant winemaker in Oregon’s Willamette Valley. But when the financial fallout from a mold-ridden home and a costly lawsuit left him nearly bankrupt, Berg rebuilt again. This time, back home in Denver, as a real estate agent.

With a newborn, another on the way, $80K in debt, and his family living in one bedroom at his in-laws’, Stephen started from zero and within two years was the Denver Metro Association of Realtors (DMAR) Rookie of the Year, discovering that the only real limits were the ones he’d been placing on himself.

Our conversation covered a lot of ground - from the danger of comparing your chapter one to someone else’s chapter twenty, to how punk rock, science, and critical thinking can shape a career and a worldview. We also dove into why structure and patience are underrated superpowers in an unpredictable industry and how fatherhood reframed his idea of success — not just as freedom of income, but freedom of time.

By the end, Stephen’s story becomes less about selling homes and more about how to build a life — one defined by adaptability, curiosity, and conviction.

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