PlayYourCourt did not start as a national tennis education company.

It started with a simpler problem: people wanted tennis lessons, public courts were available, and coaches wanted more hours. Scott Baxter saw a gap between the traditional tennis club model and the everyday player who wanted to learn without joining a private club.

“If you want instruction or community, trying to figure out how to actually get better, the money can get spent pretty similarly to golf pretty quickly,” Baxter said.

The early thesis was straightforward: make tennis lessons easier to find, easier to book and easier to access on public courts.

“I wanted more hours as a hustler, I was young, I wanted to teach more than forty hours a week,” Baxter said.

What began as a way to fill his own schedule grew into a larger marketplace. Baxter was the first coach on the platform. Over time, PlayYourCourt became, “the biggest Tennis Lessons marketplace in the world with over 3,200 coaches.”

But marketplaces are rarely simple businesses.

There is always a supply problem, a demand problem or both. Too many coaches and not enough players means coaches stop paying attention. Too many players and not enough coaches means the customer experience falls apart.

“If you’ve got a bunch of coaches but no business, then when they get booked they’re not paying attention anymore,” Baxter said. “If you’ve a whole bunch of business but you want to send them to, what are you doing?”

As PlayYourCourt grew, customers revealed another problem. Lessons were useful, but players still needed someone to hit with between lessons.

“The number one reason somebody will stop playing is that they can’t find someone to play with,” Baxter said. “And then the second reason is they can’t figure out how to get good enough where they wanna keep playing.”

So PlayYourCourt built a practice partner community. For a monthly fee, players could find evenly matched people to play with. The company grew that side of the business to more than 25,000 paid members.

Then the data started telling a different story.

The product worked. That was the problem.

Players would join, meet people and leave. From a customer standpoint, PlayYourCourt had done its job. From a business standpoint, that created churn.

“I picked up the phone and started calling customers and asking them, you know, hey, like I saw you signed up and you left,” Baxter said. “The number one response was it worked great, thank you so much. I met like nine people in two days.”

The marketplace had solved a real problem, but solving it too quickly meant customers no longer needed to stay.

“We’ve become match.com where you meet your wife one day too,” Baxter said.

That insight forced the company to look beyond the marketplace. The most valuable customers were not necessarily the ones who came for lessons or partner matching. They were the ones who stayed for educational content.

“Customers that would stick around the longest would actually come in to find partners, but they would stick around to watch our educational content,” Baxter said.

That changed the business.

Baxter and his business partner Nate had been making YouTube content as a marketing tool. The idea was to teach people something useful, build trust and then point them toward PlayYourCourt’s lesson marketplace. But the content was not just feeding the business. It was becoming the business.

“It never even crossed our mind that that was the business,” Baxter said.

PlayYourCourt has since evolved into an education company focused on helping players improve faster, no matter where they live. The lessons marketplace and partner community still matter, but Baxter now sees them as supporting pieces around the core education platform.

“Each time what I thought was the core business model has become satellites around the new core model,” Baxter said.

That evolution also explains why PlayYourCourt did not chase pickleball, despite pressure to do so. Pickleball was popular, but Baxter said the problems PlayYourCourt solved in tennis did not translate cleanly.

“Not exactly hard to find a pickleball partner right now, everybody wants to do it,” Baxter said. “Nobody’s taking pickleball lessons every single week. So like the things that we solved in the tennis spaces weren’t problems that existed for pickleball.”

The decision was not just about market size. It was about focus.

“I found that if you’re really excited about something, you’ll tend to work a lot harder on it,” Baxter said.

That focus carried PlayYourCourt through several versions of itself: a side hustle, a lessons marketplace, a partner-matching community and now an education platform.

The broader lesson is not about tennis. It is about what happens when founders pay attention to what customers actually do, not just what the original pitch said they would do.

For Baxter, the data did not just reveal a new feature.

It revealed the real business.

 

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