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November 21, 2025 64 mins

Delaware-born linebacker Debo Williams joins Kail this week to talk honest, unfiltered life after football, chasing the NFL dream, and becoming a 23-year-old tech entrepreneur. From growing up in Smyrna, grinding his way from an under-recruited high school athlete to the University of Delaware and then transferring to play SEC football at the University of South Carolina, Debo breaks down what college recruiting actually looks like.

They get into the realities of what really happens when you don’t get drafted even after calls from most of the league. Debo shares how he turned that uncertainty into purpose by launching SpendHer Hotline, an app that connects real people to real experts for paid advice on anything from podcasting to mechanics.

Debo and Kail also talk youth sports culture, parents rearranging their entire lives for kids’ athletics, when it’s time to push vs. when it’s time to pull back, and what to do when your kid is “good” but not a clear D1 star. If you’re a parent of an athlete, a student-athlete, or someone trying to pivot after a dream doesn’t go as planned, this episode is for you.

Follow Debo and download SpendHer Hotline now!

For full video episodes head to patreon.com/kaillowry


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