Alejandro Rioja runs Pickleland, an indoor pickleball facility in Austin, and spent years frustrated with the booking software every club in the industry was stuck using. That frustration turned into Courtlines, a club operating system he’s now building for racquet and court-sport businesses.
We sat down with Rioja to ask him about the AI advisor at the center of it, why he built it while still running his own club, and where he thinks this goes next.
What was actually wrong with the software you were using before?
Every booking system out there is the same — CRUD screens, a dashboard, good luck. None of it’s AI-first. I wanted something that runs itself and gets better on its own, not something I babysit.
So what does Courtlines actually do differently?
It’s booking, memberships, point-of-sale, and scheduling for racquet and court-sport facilities — pickleball, tennis, padel, squash, badminton, with room to extend into volleyball and CrossFit down the line. But the part I actually care about is the AI advisor. Every morning it reviews the club’s numbers and tells the operator what to actually do about them, instead of just showing a dashboard and leaving you to figure it out.
You’re not building this from the outside — you’re the customer too. Does that change anything?
Completely. I wasn’t guessing at the pain points — I was living them. Different kind of insight when you’re the operator, not just building software for one.
Has it actually moved the needle for Pickleland?
Pickleland runs on Courtlines end-to-end, not as some pilot bolted onto our old tools. We’ve seen roughly a 25% revenue increase since making the switch, and I’d credit the morning recommendations for a lot of that, not just the booking flow itself.
Where do you want to take this beyond pickleball courts?
Short term, club OS for racquet sports. Long term I want this running any small business that lives on time slots and memberships — gyms, salons, whatever. Started with courts because that’s the world I know. But the itch was never just pickleball, it’s “why is this software so dumb.”
Rioja calls Pickleland the hardest business he’s built — high fixed costs, hands-on customers, nowhere to hide — and says building Courtlines himself wasn’t a side project, it was the only way to get software that fit how he actually runs the business. Courtlines is early. Pickleland is the proof of concept; whether it works for clubs Rioja doesn’t personally run is the next test.
Learn more about Courtlines at courtlines.com, or follow Alejandro Rioja at alejandrorioja.com.
