Building in Public: The Hardest Part About Building in a “Traditional” Industry

On the surface, software is software. You identify a problem, build a solution, and bring it to market. In reality, it doesn’t work like that here.

Clubs don’t just adopt new technology because it’s better. They adopt it when it fits into how they already operate, and when they trust the people behind it. A lot of these facilities have been running for years, sometimes decades, with systems and processes that may not be perfect but are familiar. Changing that isn’t just a product decision, it’s a relationship decision.

There’s also a real cost to change that I didn’t fully appreciate at first. It’s not just about switching software. It’s retraining staff, adjusting workflows, communicating changes to members, and taking on the risk that something might not go smoothly. Even if what you’re offering is clearly better, that transition can feel like more pain than it’s worth.

Another thing that stands out is how relationship-driven everything is. In a lot of SaaS markets, you can lean heavily on product-led growth. Here, conversations matter more. Trust matters more. Reputation matters more. People want to know who they’re working with, not just what the product does.

And then there’s the balance between innovation and practicality. It’s easy to sit on the outside and think, “Why don’t clubs just do this differently?” But once you’re closer to it, you realize there are reasons things are the way they are. Constraints around staffing, budgets, member expectations, and even culture all play a role. You can’t just drop in something completely new and expect it to work.

All of this has forced me to rethink how we approach building CourtMatch. It’s not just about creating something better, it’s about creating something that fits. Something that reduces friction instead of adding to it. Something that works with how clubs operate today while still helping them move forward.

I’m still figuring out that balance. How far to push, how much to adapt, and where the real leverage points are.

For those who’ve worked in or around clubs for a long time, where do you see the biggest resistance to change, and what actually helps overcome it?