Who is PADDLEMORE?

Our Founder & Chief Paddle Officer is Ben Castleberry a proven entrepreneur with a track record of starting, scaling, and exiting multiple multi-million dollar businesses. From building a nationally recognized healthcare technology company to acquiring and growing one of the world’s top triathlon brands, Ben understands what it takes to launch, operate, and grow high-performance companies in highly regulated environments.

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He’s led successful ventures across industries—from healthcare to clean tech to consumer products—and has executed multiple exits, each one sharpening his focus on delivering scalable, operationally lean solutions that solve real-world problems.

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Ben also has extensive experience working directly with government agencies and state park systems, most notably in his company Car Charging Pros partnership with Rivian, where he installed electric vehicle charging infrastructure deployments across public lands. That initiative gave him a deep appreciation for the complexities and sensitivities of working with public-sector partners—and how to do it right.

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After exiting TriRig in a seven-figure sale, Ben turned his attention to one of his greatest personal passions: paddling. A lifelong lover of the outdoors, he found inspiration in his own experiences kayaking in national and state parks and recognized a huge opportunity to modernize how people access watercraft in outdoor recreation spaces.

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That’s where PADDLEMORE was born.

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What started as a simple idea—self-serve kayak and SUP rentals through beautifully wrapped, solar-powered smart kiosks—has grown into a platform poised to reshape how resort operators, campground owners, and even large hotel groups manage recreation access.

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Unlike traditional activity shack models that require full-time staffing, equipment maintenance, and operational oversight (with all the HR headaches that come with it), PADDLEMORE offers a fully automated, zero-headache, 24/7 rental experience that improves margins and simplifies operations. The system is designed to place the responsibility on the renter, not the resort—reducing liability and increasing accountability through credit card holds, smart tech, and clear rental terms.

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For resort and park operators, PADDLEMORE provides better revenue share terms than most third-party vendors, while requiring no upfront capital, no staffing commitments, and no day-to-day management.

For guests, it’s a seamless, app-driven experience that unlocks more time on the water and less time waiting in line or wondering when the shack opens.

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If you’re a campground, lakefront resort, or city park manager looking for a reliable partner to enhance your property’s guest experience—while putting more money in your pocket—Ben and the PADDLEMORE team are ready to talk.