The Operator-Turned-Founder Story Proving the Power of Modern Hospitality Tech

The Founder Story We All Need to Hear Right Now

Pickleball clubs now function as full-blown social destinations, breweries serve as community living rooms, and guests demand frictionless experiences wherever they go. Hospitality looks nothing like it did ten years ago. The most successful founders aren’t just operators or tech builders. They’re both. And that’s how they’re winning.

One of the best examples is Ashley Owens, co-founder of CourtReserve, a platform now powering thousands of court facilities around the world. What began as a frustration with paper court sheets and phone-based reservations has transformed into one of the most compelling growth stories in modern hospitality tech, culminating in a $54 million investment to accelerate their mission. We were honored to have the opportunity to speak with Ashley in our latest Behind the Tab Podcast episode available today on Spotify, Apple Podcasts and more.

This is the kind of founder story that resonates: part operator, part technologist, part community builder, and all grit.

The Pain Point That Started CourtReserve

Ashley and her husband Tim weren’t trying to start a tech company.

They were tennis players.

They were driving 20 minutes to their club, putting their names on a whiteboard, and waiting, hoping someone else knew what was happening behind the scenes. Lessons? Court availability? Programming? It was all word-of-mouth.

So they did what every great hospitality founder does when they're frustrated: They built the solution they wished existed.

Armed with Tim’s software background and Ashley’s sales and marketing experience, they sketched out the earliest version of CourtReserve in their kitchen. The mission was simple: bring structure, visibility, and professionalism to racquet sports facilities that were still operating like it was 1999.

Their first customer got the software for $75 at a silent auction—and then helped them build it.

That scrappy, operator-first mindset? It has stayed with them ever since.

When Operators Become Entrepreneurs

Many software founders build tools for industries they’ve never stepped foot in. Ashley and Tim took the exact opposite path.

They opened Old Coast Pickleball, an indoor club in St. Augustine, Florida. They didn’t do it because they needed a hobby. They did it because they needed a laboratory.

• A place to test features.
• A place to get live feedback.
• A place to feel every operational challenge their customers feel.

This was their advantage.

They didn’t just build software for court operators. They became court operators themselves.

Today, their firsthand experience is what makes CourtReserve resonate so deeply with facility owners. They’ve lived the pain of managing schedules, juggling instructors, handling payments, keeping communities engaged, and reinventing programming to stay competitive.

Ashley’s insight mirrors what the most successful hospitality entrepreneurs already know: “Passion gets you started. But business discipline is what keeps the doors open.”

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Why CourtReserve Took $54M

For nearly a decade, Ashley and Tim bootstrapped CourtReserve, growing it steadily and shaping it with feedback from real clubs. But eventually, the demand outpaced their ability to grind.

Operators wanted more:

• More integrations.
• More automation.
• More support.
• More innovation.

So in 2025, CourtReserve took a strategic step by partnering with MainSail Partners for a $54 million investment to accelerate their roadmap. This wasn’t about selling out. It was about protecting their culture and growing their community.

With new funding secured, they’re doubling down on the work their operators have been asking for. They’re strengthening CourtReserve's integrations with platforms like GoTab, expanding their team and quality assurance efforts, and launching a “Catalyst Tour” that will take them to facilities across the U.S. and Canada. They’re also building advisory boards made up of real venue owners and accelerating their product innovation to keep pace with a rapidly evolving industry.

This isn’t just a tech company getting bigger. It’s a hospitality story about scaling without losing your soul.

The Boom: Pickleball, Padel, Multi-Sport, and the Rise of Lifestyle Venues

Beyond CourtReserve’s entrepreneurial journey, Ashley shared something every hospitality operator should pay attention to:

We’re in one of the biggest recreation booms in decades.

Pickleball is exploding. Padel is surging. Badminton, squash, and multi-sport facilities are reinventing themselves. Golf simulators are becoming standard add-ons. Even tennis is having a renaissance.

The modern “sports club” isn’t a single-sport venue anymore. It’s an entertainment destination.

The winners are the operators who pivot early—those who add courts, diversify programming, modernize operations, and build clubs where people want to gather. As Ashley put it: “The most successful clubs are the ones pivoting and giving people choice.”

This is the same entrepreneurial mindset seen in breweries, entertainment venues, and hybrid hospitality spaces across the country: diversify your revenue, modernize your operations, and build community relentlessly.

Passion Isn’t Enough—It’s the Business Model That Wins

One of the most refreshing parts of Ashley’s story is her honesty about failure. She’s seen passionate pickleball lovers open clubs with great intentions but poor business structure. And they close quickly.

It's the same pattern seen across hospitality:

• Passion without process
• Talent without systems
• Great product without diversification
• Community without consistency
  
  

The hospitality entrepreneurs who succeed long-term are those who balance love of the craft with love of the business.

As Ashley says: “You have to do what you’ve got to do until you get to do what you get to do.”

It’s a rallying cry for every founder cleaning bathrooms, fixing software bugs at midnight, or answering membership calls between coaching sessions.

Tech + Hospitality: Why Openness Beats “All-In-One”

Ashley and GoTab’s CEO, Tim McLaughlin, share the same ethos:

Operators should never be forced into locked-down, closed systems.

Hospitality thrives on interoperability. Facilities thrive when they can choose best-in-class tools. Guests thrive when technology is seamless.

This is what makes the GoTab + CourtReserve integration so powerful: Two operator-founded companies building tech that actually matches real-world needs. It’s the opposite of the “my-way-or-the-highway” POS or facility management giants. And it’s exactly the kind of partnership modern hospitality founders gravitate toward.

A Hospitality Entrepreneur Story Still Being Written

From a kitchen whiteboard to a nationwide movement, Ashley’s story mirrors the trajectory of thousands of hospitality entrepreneurs redefining what it means to build successful venues and hospitality technology.

Her journey reflects a new era of hospitality leadership where founders are:

• Operators and innovators
• Technologists and community builders
• Strategists and storytellers
• Passionate and disciplined
  
  

CourtReserve’s story isn’t finished. The boom isn’t over. And the needs of operators are evolving faster than ever.

But one thing is clear: This is exactly the kind of founder story the hospitality world wants and needs to hear right now.

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