In this conversation, Tyler O'Shea, founder of Joker Mag and author of The Underdog Mentality, joins Nik to explore the power of underdog stories in sports. From being cut from his middle school baseball team to building a platform that champions overlooked athletes, Tyler shares how self-belief, resilience, and storytelling fuel both personal growth and cultural impact. They dive into the traits that define successful underdogs, highlight figures like Michael Jordan, Bryce Harper, and Howie Roseman, and discuss the challenges creators face in staying focused and consistent. The result is a powerful reflection on adversity, motivation, and redefining success.

If you’ve ever felt underestimated, this one’s for you.

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