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Episode 87: Josh Skillman (Co-host of a podcast with his 10 year old son)
🎙 This week on the Youth $ports Podcast: I sit down with Josh Skillman, co-host (alongside his 10-year-old son Luke) of the podcast Always Pick the Underdog, to talk about creativity, connection, and why youth sports don’t have to be the only bonding experience between parent and child.
🔹 What started as a simple weekly Facebook post breaking down upcoming football games slowly grew into something bigger. A niche audience began tuning in consistently...
🔹 In 2024, Luke (Josh's 10 year old son) joined as a “guest picker.” One season later, Josh upgraded the equipment… and what began as his adventure became their adventure.
🔹 Now? Luke drives the show. He selects the games, builds the slides, and helps shape the direction. There’s no over-rehearsing and no pressure to be perfect.
🔹 The #1 rule of the podcast: Have fun. If it stops being fun, it stops working.
🔹 Their following has grown, and they now feature guest pickers weekly — creating community around something that simply started as shared interest.
🔹 A powerful reminder: your child’s sport does NOT have to be the only connection point in your relationship. Shared experiences can exist outside the field, court, or diamond.
🔹 Josh was intentional about not forcing sports onto his kids. Knowing how much they meant to him, he allowed interest to develop naturally and that organic curiosity created deeper buy-in.
🔹 The podcast reshaped their father-son dynamic. Josh admitted he sometimes misread Luke’s perfectionism or quietness. Working side-by-side gave him more patience and understanding.
🔹 Their mornings now start the same way: Luke checking scores, the two of them talking football over breakfast and bonding regardless of whether yesterday was a good day or a tough one.
🔹 The show has fueled Luke’s creativity and academic growth: improved spelling, public speaking, design skills, Canva presentations, and confidence.
🔹 On the podcast, they operate on equal footing. It’s not Dad coaching and Luke performing. It’s collaboration.
🔹 Hosting a sports podcast has also deepened Luke’s appreciation for watching full games and not just highlights. We talked about how today’s kids consume sports differently, and why actually WATCHING games (not just clips) helps young athletes understand nuance, spacing, tactics, and details (think: the subtle reads within a ball screen).
This episode is a reminder that sometimes the best thing you can do as a sports parent… is pick the adventure.
And make sure it’s fun.
By Ally Tucker5
6767 ratings
Episode 87: Josh Skillman (Co-host of a podcast with his 10 year old son)
🎙 This week on the Youth $ports Podcast: I sit down with Josh Skillman, co-host (alongside his 10-year-old son Luke) of the podcast Always Pick the Underdog, to talk about creativity, connection, and why youth sports don’t have to be the only bonding experience between parent and child.
🔹 What started as a simple weekly Facebook post breaking down upcoming football games slowly grew into something bigger. A niche audience began tuning in consistently...
🔹 In 2024, Luke (Josh's 10 year old son) joined as a “guest picker.” One season later, Josh upgraded the equipment… and what began as his adventure became their adventure.
🔹 Now? Luke drives the show. He selects the games, builds the slides, and helps shape the direction. There’s no over-rehearsing and no pressure to be perfect.
🔹 The #1 rule of the podcast: Have fun. If it stops being fun, it stops working.
🔹 Their following has grown, and they now feature guest pickers weekly — creating community around something that simply started as shared interest.
🔹 A powerful reminder: your child’s sport does NOT have to be the only connection point in your relationship. Shared experiences can exist outside the field, court, or diamond.
🔹 Josh was intentional about not forcing sports onto his kids. Knowing how much they meant to him, he allowed interest to develop naturally and that organic curiosity created deeper buy-in.
🔹 The podcast reshaped their father-son dynamic. Josh admitted he sometimes misread Luke’s perfectionism or quietness. Working side-by-side gave him more patience and understanding.
🔹 Their mornings now start the same way: Luke checking scores, the two of them talking football over breakfast and bonding regardless of whether yesterday was a good day or a tough one.
🔹 The show has fueled Luke’s creativity and academic growth: improved spelling, public speaking, design skills, Canva presentations, and confidence.
🔹 On the podcast, they operate on equal footing. It’s not Dad coaching and Luke performing. It’s collaboration.
🔹 Hosting a sports podcast has also deepened Luke’s appreciation for watching full games and not just highlights. We talked about how today’s kids consume sports differently, and why actually WATCHING games (not just clips) helps young athletes understand nuance, spacing, tactics, and details (think: the subtle reads within a ball screen).
This episode is a reminder that sometimes the best thing you can do as a sports parent… is pick the adventure.
And make sure it’s fun.

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