Military lessons that sustained entrepreneurship

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Alpha Coffee co-founder and retired Army lieutenant colonel Carl Churchill joins Joe for a candid conversation on leadership, resilience, and what it really takes to build something that lasts after the uniform comes off.

After serving more than two decades in the Army, Carl found himself facing an unexpected second career shaped not by careful planning, but by crisis. In the wake of the Great Recession, he and his wife Lori cashed out their savings and took an all-in leap to build Alpha Coffee from their basement—navigating years of uncertainty, near-misses, and hard-earned lessons before the business finally found its footing. Drawing on his military background, Stoic philosophy, and a refusal to quit, Carl shares how discipline, culture, and clarity of purpose carried him through nearly a decade of struggle.

In this conversation, Joe and Carl explore what leadership looks like when there’s no rank to hide behind: how military lessons translate into entrepreneurship, why culture matters more than strategy, and how leaders must adapt their style as contexts and generations change. Along the way, they reflect on stress, perspective, boundaries, and the quiet confidence that comes from having faced truly hard things before.

In this episode, Joe and Carl also explore:

• Tips for making great coffee
• Why Carl chose to walk away from promotion to keep leading people, not staffs
• What “burning the boats” looks like when your family and future are on the line
• How military hardship inoculates leaders against stress and uncertainty
• Why culture—not strategy—is the true differentiator between great and failing teams
• Leading younger generations without abandoning standards or expectations
• The challenge of setting boundaries when you genuinely love your work

Whether you’re navigating life after military service, building something from scratch, or leading people through uncertainty, this episode offers a grounded reminder that the habits forged in discipline, humility, and persistence still matter—long after the mission changes.

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