There’s a moment at every conference, usually somewhere between the second coffee and the first cocktail, where the conversation loosens up and people start saying what they actually think.
Buying Sandlot had a lot of those moments - in a good way.
I was fortunate to be at the conference and hosted a panel on Preparation and Safety with an incredible group of people. Ellis Mair from GO4, Seth Lieberman from Ankored, Tyrre Burks from Players Health, and Kate Quattlebaum from NCSI. For you safety and opps nerds, it was a treat.
First off, credit where it’s due: The Buying Sandlot team put together a thoughtful, well-run event. The room was filled with smart operators, serious investors, and people who clearly care about where youth sports is headed. It didn’t feel like a vanity exercise. It felt like a real attempt to grapple with what this space is becoming.
And that’s where things got interesting.
Because underneath the energy and opportunity, there was a quiet tension running through a lot of conversations, a disconnect between operators and investors that’s hard to ignore once you see it.
Jake Deane, the Founder of True Lacrosse,
put it plainly in his post: investors are looking for clean, scalable, high-margin businesses. The challenge is that youth sports doesn’t naturally produce those. It’s fragmented, operationally messy, and built on relationships and trust more than systems and scale.
So you end up with two groups looking at the same thing through very different lenses.
On paper, the playbook is familiar - standardize, professionalize, scale. In practice, it gets complicated. Sports don’t happen in a boardroom. They happen on fields, in parks, with coaches and families who care far more about the experience than the efficiency behind it.
There’s a certain magic to that. And like most things with a bit of magic, it doesn’t hold up particularly well when you try to over-optimize it.
That doesn’t mean there isn’t real opportunity here. There absolutely is. But it comes with constraints. You can only squeeze so much efficiency out before you start chipping away at the very thing people value.
Youth sports aren’t retail chains or service rollups. They’re closer to communities. And communities tend to resist being turned into systems.
What was encouraging, and this is where Buying Sandlot deserves a lot of credit, is that most people in the room seemed to discuss that balance. There was a genuine awareness that this space requires a different kind of thinking, and a willingness to talk about it openly.
That’s not nothing. In fact, it’s probably the most important starting point. Because if this next phase of youth sports is going to work, it won’t come from forcing a familiar model onto an unfamiliar space. It’ll come from aligning capital and operators around what actually drives value here, and having the discipline to protect it.
Otherwise, families won’t send feedback. They’ll just quietly walk away, and no amount of optimization fixes that.
