Everett Osborne on Reinvention, Faith & Becoming Someone New from First Round's on Me

First Round's on Me

First Round's On Me

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Everett Osborne on Reinvention, Faith & Becoming Someone New

45 minutes Posted Apr 27, 2026 at 10:35 am.

Intro00:31 Meet Everett Osborne01:49 Growing Up With Big Dreams03:21 From D1 Basketball to Playing Pro04:37 The Opportunity That Changed Everything06:07 Playing Basketball in Australia07:19 Being Close to a Life-Changing Dream09:05 Leaving Basketball Behind10:23 Discovering Acting During COVID12:21 Identity, Reinvention & Starting Over14:37 Life as a Video Game16:37 The Power of Human Connection19:22 Faith, Purpose & Something Bigger21:21 Curiosity and Asking Bigger Questions22:31 Fear of Failure23:20 Effort vs. Outcome25:20 How Basketball Prepared Him for Acting28:30 Landing the Role of Sweetwater30:16 Carrying a Forgotten Legacy32:29 Favorite Moments on Set34:10 The Full-Circle Coach Moment35:38 Who Was Sweetwater Clifton?38:18 Acting Through Real Historical Pain40:40 One Purpose or Multiple Chapters?41:38 What This Chapter Is Teaching Him42:28 Advice for Feeling Stuck44:28 Where to Find Everett45:05 Outro

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Actor and former professional basketball player Everett Osborne joins First Round’s On Me for a powerful conversation about reinvention, identity, faith, failure, and the courage it takes to start over. Everett opens up about walking away from basketball, stepping into acting, starring as Sweetwater Clifton, and learning how to trust the process when life forces you into a new chapter.Joe, Hannah, and Everett also dive into purpose, ego, personal growth, faith, the pressure of chasing a dream, and why the journey matters just as much as the destination.

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