What happens when the business you built is not the business your customers actually want?
PlayYourCourt started as a way to make tennis lessons easier to find and book. But as the company grew, the data told a different story. Customers were using the platform, getting what they needed, and leaving. That churn forced the company to look closer at what people were really paying attention to.
In this episode of Fervent Four, PlayYourCourt founder Scott Baxter shares how the company evolved from a tennis lessons marketplace into a broader education platform after customer behavior revealed the real opportunity. We get into the grind of building a two-sided marketplace, what churn can teach a founder, how YouTube and content became a major part of the business, and why focus mattered more than chasing the pickleball boom.
Scott also talks about raising money the hard way, learning from early fundraising mistakes, building in Virginia Beach, and the long path from side hustle to a business that can last.
For more information on PlayYourCourt, visit:
https://www.playyourcourt.com/
00:00 The pitch that changed everything
00:29 What is PlayYourCourt?
03:12 Why tennis can feel expensive
05:01 From country club coach to founder
07:08 Why marketplaces are hard
09:01 Chasing professional tennis
14:02 How tennis prepared him for business
16:01 Why PlayYourCourse didn't work
17:27 Failure, coaching and business advisors
18:19 Growing up around work and entrepreneurship
21:07 Choosing tennis after college
24:24 The first big PlayYourCourt pivot
27:12 From lessons to practice partners
29:20 The problem with marketplace churn
30:23 How YouTube became the real business
36:40 Building the education platform
39:03 The funnel behind tennis content
40:04 Why PlayYourCourt said no to pickleball
43:26 Raising money the hard way
47:26 The accelerator pitch that changed the round
49:34 Why EO matters for CEOs
51:12 Shrinking the team and simplifying the model
53:18 The real-life impact of tennis community
55:07 What's next for PlayYourCourt
56:11 Local food, recovery and routines
57:02 Fundraising lessons founders should know
