Darren Hornig had a billion-dollar IPO on the shelf in 1999, then the dot-com bubble took it all down. In this episode, the serial entrepreneur behind the John McEnroe Tennis Academy and six pickleball facilities breaks down how he turned a real estate play into a racket sports empire, why he built Courtsap to be the Expedia of tennis and pickleball, and how the data his app collects, from when you play to when your strings need replacing, could make it worth a billion dollars all over again.
Episode 26: Building the Expedia of Racquet Sports with Daren Hornig
What happens when a real estate investor stops choosing an asset class first and lets the opportunity reveal what it can become? For Daren Hornig, that mindset has led from commercial leasing and telecommunications to billion-dollar real estate development and an AI-powered racquet-sports platform.
In this episode, Mike and Zach sit down with entrepreneur and investor Daren Hornig to unpack a career built around curiosity, resilience, and scale. Daren shares how he grew a fiber-optic infrastructure company to 500 employees, weathered the dot-com collapse, returned to real estate, and diversified across office, residential, retail, and industrial properties.
We dig into the acquisition of the Port Washington Tennis Academy and how a real estate opportunity became a growing sports business. After partnering with Sportime and establishing Sportime Port Washington, home to the John McEnroe Tennis Academy, Daren expanded further into pickleball facilities across the Northeast.
One of our biggest takeaways is Daren’s approach to vision: stay open enough to let the opportunity define the highest and best use. That same thinking led to CourtsApp, a marketplace designed to help players discover and book courts while helping facilities fill unused time and make smarter decisions.
You’ll also hear how CourtsApp plans to use AI through its “Hey Courtney” agent, why customer data can unlock dynamic pricing and better service, how platform businesses scale without owning every underlying asset, and why Daren still chooses building and growth over retirement.
“I let opportunity drive my vision, and I don’t let my vision drive opportunity.”
“I like building. I like being dynamic. I like going for it.”
“The data is the treasure trove.”
“Life’s too short. I don’t need to buy headaches. I don’t need to have bad partners.”
Daren Hornig is the founder and Chief Executive Officer of CourtsApp, the first AI-powered booking platform built for racquet sports such as tennis, pickleball, padel, and squash.
Daren is also Managing Partner of Hornig Capital Partners, bringing over 35 years of experience as a real estate broker, telecommunications entrepreneur, investor, and developer. Since founding HCP in 2013, he has acquired and developed over $1 billion in office, residential, retail, and industrial properties.
In 2023, Daren acquired the famed Port Washington Tennis Academy and partnered with Sportime to establish Sportime Port Washington, home to the John McEnroe Tennis Academy. Following an $8 million renovation, the facility now features 13 tennis courts, 12 pickleball courts, and two golf simulators. He later partnered with Sportime to expand dedicated pickleball facilities throughout the Northeast.
A 1989 graduate of the University of Maryland, College Park, with a bachelor’s degree in Business Marketing, Daren resides in New York and Florida. When he is not building companies, developing properties, or opening new pickleball facilities, you can find him on the courts or the slopes.
Find Daren Hornig on LinkedIn, visit CourtsApp, or email info@courtsapp.com
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