EP207 - Ex-Nike Director Exposes the High Cost of ‘Winning’
In this episode of The Tyler Dickerhoof Show, Tyler Dickerhoof welcomes former Nike executive and author of Worthy Wins: Pointing Your Life Toward What Matters Most, John Olinger, for a powerful conversation on purpose, loss, and redefining success.
As Nike’s Global Brand Director for Kobe Bryant, John led one of the most emotional campaigns in the company’s history following Kobe’s tragic death. But behind the dream job and high-level wins was a deeper tension—between achievement and alignment, performance and people, career and calling.
John opens up about what Kobe’s legacy taught him, why most leaders are chasing empty goals, and how personal tragedy forced him to reassess everything. From boardrooms to burnout, he shares how ambition can quietly wreck relationships—and how small, consistent actions can build a life that actually matters.
Together, they unpack the cost of climbing the wrong ladder, the trap of tying identity to success, and the power of taking a pause before it’s too late. If you're feeling stretched, stuck, or unsure what really counts—this conversation is a reset.
John Olinger
John Olinger spent a decade as a Brand and Digital Marketing leader for Nike and Jordan Brand, including three years captaining Global Marketing for Kobe Bryant. He reached a career inflection point after the unexpected passing of his father and left Nike in late 2022. His story and the biggest learnings from his career at Nike are featured in his new book, Worthy Wins, that launched on June 10. John now works as a strategic consultant, executive coach, and keynote speaker, in addition to being the CEO and CMO of Unitus, a faith-forward footwear and apparel brand. He lives in Florida with his amazing wife, Erin, and their three boys.
IN THIS EPISODE WE DISCUSS:
00:00 Introduction
01:25 Why the dream job isn’t always the dream
03:18 How a tribute to Kobe became a life-altering moment
07:53 Climbing the right ladder starts with the right building
13:42 What Kobe’s post-NBA life revealed about true wins
18:27 The true cost of chasing the wrong wins
21:39 If it’s worth it, it’s worthy
25:04 How to know when it’s time to leave a great job
29:38 What makes someone a great leader?
35:39 How personal struggles affect workplace performance
38:24 Two ways personal chaos shows up at work
43:40 What do you want your corporate obituary to say?
Resources, books, and links mentioned in this episode:
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About the Tyler Dickerhoof Show Podcast
The Impact Driven Leader Podcast, hosted by Tyler Dickerhoof, is for Xillennial leaders who have felt alone and ill-equipped to lead in today's world. Through inspiring interviews with authors from around the world, Tyler uncovers how unique leadership strengths can empower others to achieve so much more, with real impact.
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