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May 21, 2025 40 mins

It’s hockey tryout season. And for many families, that means stress, judgment, and silent pressure behind the glass. Let’s be clear: this isn’t a takedown of competitive sports — it’s a wake-up call for the grownups in the room.

In this powerful and personal episode, I’m joined by Jessica McCoy — investment professional, fierce hockey mom, and one of my closest friends — to talk about what’s really going on behind the scenes of youth sports.

We cover:

  • The real cost of raising competitive athletes — financially, emotionally, and mentally
  • The toxic parent culture that’s infecting team environments
  • What success actually means for kids (hint: it’s not scholarships or medals)
  • How we, as adults, can do better at raising good athletes and good humans


With tryouts happening right now for the upcoming hockey season, this conversation couldn’t be more timely. Our hope is that it inspires parents, coaches, and kids to show up a little differently — with more compassion, more perspective, and a lot more heart.

Whether you’re a parent, coach, or educator — this one’s for you.

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