With a rooted love of the outdoors and military background, Will built Sentinel Overland with a simple mission: to help people become more capable in the wild. His background forged hands-on problem solving with real-world leadership. Will leads each trip with an emphasis on self-reliance, trail awareness, and quiet confidence. Whether he’s guiding a first-timer through their first off-camber trail or coordinating a multi-rig convoy, Will brings grit, patience, and a deep knowledge of what it takes to venture far and return ready for more.

With decades of experience behind the wheel and in technical troubleshooting, Gilbert brings steady wisdom and direction to the Sentinel Overland crew. Known for his stoic problem-solving and strong hands-on intuition, he’s the one people look to when the trail throws something that requires a zoomed-out perspective. Whether he’s walking a rig through a rocky section or sharing stories around the fire, Gilbert carries a legacy of resilience, excellence, and respect for the land.

With an eye for the moment, Josh adds his creativity as a photographer to his skills on the trail and at camp. A fellow lover of the outdoors and lifelong friend, Josh has brought Sentinel Overland to life with his passion, his unique ability to capture candid moments forever with the perfect photo, and his grit when faced with challenges. He’s put his media expertise to work, drawing the eye of trusted brands and gaining hands-on access to a wide range of gear, sharpening the crew’s experience and raising the bar for every run we lead.