Building in Public, Part 7: The Unexpected Challenges of Building a Two-Sided Community

Make it easier to find people to play with, discover opportunities to play, communicate with other members, and ultimately spend more time on the court. If we could make that experience great, I assumed the rest would naturally follow.

What I underestimated was how dependent that experience is on the club. You can build the best matchmaking experience in the world, but it isn't particularly useful if there aren't enough players participating. You can make it incredibly easy to discover leagues, ladders, tournaments, and open play, but someone still has to create those opportunities. The player experience and the club experience aren't separate problems. They're completely dependent on each other.

That creates an interesting challenge for us because we're essentially building for two customers at the same time. Club operators want fewer administrative tasks, better utilization, easier programming, and more engaged members. Players don't care about any of that. They want to open an app and quickly figure out when they can play, who they can play with, and what's happening at their club. If either side of that equation doesn't work, the entire experience suffers.

I've also learned that community features have a cold-start problem. A new member joining a club shouldn't have to already know ten people before CourtMatch becomes useful. In fact, I think the exact opposite should be true. The person who knows nobody is probably the person who needs the platform the most. But creating that experience requires more than putting a "find players" button in an app. You need enough information about players, enough opportunities to participate, and enough activity happening within the community for those connections to actually happen.

This has changed the way we think about a lot of what we're building. Instead of asking whether a feature is useful for the club or useful for the player, we're increasingly asking what happens on the other side when someone uses it. If a director creates a new program, how do we make sure the right members discover it? If a player wants a match Saturday morning, how do we make it easy for that request to turn into an actual game without creating more work for the staff?

I think that's where some of the biggest opportunities in racquet sports technology still exist. Clubs have historically had software for managing the club and players have had apps for finding people to play with. I'm increasingly convinced those experiences shouldn't be disconnected. The club is the community, and the technology should make that community easier to participate in.

We're still figuring out exactly how all of those pieces should work together, but it's become one of the parts of building CourtMatch that I find most interesting. If we get it right, the technology almost disappears. More people simply find games, meet other members, participate in programs, and play more often. And ultimately, that's the outcome we're trying to create.