There’s something powerful about the grind. You build in silence, stack bricks no one sees, and one day the noise catches up. That’s CourtReserve right now, a racquet & paddle sports SaaS out of St. Augustine, FL that just turned 9 yrs of bootstrapped hustle into a $54M growth investment from Mainsail Partners. For nearly a decade, Tim Owens & Ashley Owens built this platform the hard way, no VC dollar, no shortcuts, just code, customer obsession & courts running smoother than a Federer backhand. This is what happens when product-market fit isn’t theory, it’s lived experience.
It started outside Charlotte, NC. The Owens duo, players, parents, & coaches, kept showing up to whiteboards covered in scribbled court times. Tim Owens, a developer who’s logged hours at LendingTree, Jackrabbit Technologies & Ramp51, saw a system problem. Ashley Owens, a former High Point Police Dept officer turned marketing powerhouse, saw a business one. Together they built CourtReserve from scratch, launching in 2016 as a nights-&-weekends project. By 2018, they’d grown 738% organically. Now? 2K+ clubs, 5M players, & a platform that’s become the digital backbone of racquet sports worldwide.
CourtReserve isn’t just court booking, it’s the ops engine for clubs. Memberships, payments, events, instructor scheduling, branded apps, AI insights, it runs the full match. It integrates with Stripe, Brivo, RemoteLock, DUPR, & the USTA’s World Tennis Number. The company even opened Old Coast Pickleball Club right next door to HQ, a live testing lab where product meets play. This isn’t a side app. It’s the infrastructure for a sport exploding in real time.
Mainsail Partners, the Austin & SF-based growth equity firm that just closed its $1.535B Fund VII, saw what others missed. They back founder-led B2B software that scales on performance, not hype. Jason Frankel, Partner at Mainsail & one of PE’s sharpest operators, joins the board. The plan: scale the architecture, push AI & predictive analytics, deepen integrations, & expand the team across sales, marketing & product. The timing’s perfect. Pickleball alone is growing at 12.2% CAGR, while the U.S. racquet sports market is tracking from $5.15B in ’24 to $7.74B by ’30.
CourtReserve’s not chasing the wave, they’re building it. From handwritten schedules to cloud-based ecosystems, Tim Owens & Ashley Owens turned frustration into a platform & a platform into momentum. With Mainsail Partners fueling the next serve, CourtReserve isn’t just managing the game, they’re redefining how it’s played.
