Marine Corps Officer to Entrepreneur: Daniel Medina on Leadership and Building a Brand episode artwork

EPISODE · May 5, 2026 · 47 MIN

Marine Corps Officer to Entrepreneur: Daniel Medina on Leadership and Building a Brand

from The Path That Makes Us · host Will Holbrow, Ari Levine

In this episode, former Marine Corps officer Daniel Medina joins The Path That Makes Us to talk about one of the harder transitions a person can make: moving from the structure and clarity of military service to the uncertainty of building a business from the ground up. He shares what resilience actually looks like when the stakes are real, how the leadership lessons forged in the Corps shaped his approach to entrepreneurship, and what the path into founding Restless taught him about pivoting without losing sight of the mission. Daniel also weighs in on a question a lot of people in transition are sitting with right now: whether entrepreneurship, business school, or some combination of both is the right next move, and how to tell the difference before you commit.Restless Website: https://restlessco.co/Chapters00:00 Introduction to Daniel Medina03:13 Military Background and Leadership Lessons06:22 Transitioning from Military to Business09:13 Entrepreneurship Journey and Community Impact12:22 Building Confidence and Credibility15:19 Choosing Business School and Career Paths18:11 Identifying Problems to Solve21:01 Unexpected Challenges in Entrepreneurship24:12 Formulation and Building Restless25:39 The Journey of Restless: From Concept to Launch28:22 Overcoming Challenges and Staying Motivated31:05 Prioritization and Balancing Life at Kellogg35:33 Strategic Vision for Restless: Future Goals42:07 Navigating Life's Pressures and Finding Fulfillment45:29 Rapid Fire Round: Insights and Favorites

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Marine Corps Officer to Entrepreneur: Daniel Medina on Leadership and Building a Brand

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