EP111: Leadership Lessons From The Baseball Diamond To The Boardroom with Brad Stillman Part 1

On this episode of "Into the Unknown" What if the worst leaders you've worked with taught you the most? In Part 1 of this deeply personal and insightful conversation, host Jeremy Swick sits down with fintech executive and youth coach Brad Stillman to unpack the surprising intersections of leadership, card collecting, and community building. From running tech teams at MasterCard to accidentally becoming a little league coach, Brad shares how meeting people where they are — whether in business or on the baseball field — is the key to sustainable success.

You’ll hear stories of early leadership moments, how a childhood passion for sports cards turned into life lessons, and why authentic mentorship still matters in today’s fast-paced, title-chasing world. Brad’s take on the difference between leading and managing will have you rethinking how influence is built — and why emotional intelligence trumps ego every time. Part 2 picks up next week with even deeper lessons on growth, humility, and transformation.

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