Jason Sisley is a lifelong explorer, father, and storyteller whose adventures have carried him across the globe—from riding horses through the peaks of Patagonia, to tracking wildlife on safari in South Africa, to exploring the coastlines and countryside of Portugal, Ireland, and Austria on horseback. What began as international adventure travel eventually evolved into a passion for outdoor experiences closer to home—specifically, overlanding as a way to create meaningful, child-led exploration with his family.

Today, Jason is the founder of Outland Club, a family-focused overlanding retreat program designed to help parents and children build confidence, connection, and comfort in the outdoors. Whether leading families along forest roads, teaching camp setup skills, or guiding parents through their first overland trip, Jason’s goal is to make adventure simple, approachable, and unforgettable.

As a career marketing strategist with more than 15 years of experience leading teams, building brands, and designing experience-driven campaigns for national clients, Jason brings a unique blend of professional expertise and personal passion to Outland Club. His background in behavioral strategy helps him understand how people learn, how they build emotional connections to experiences, and why comfort and confidence play such a critical role in shaping lifelong adventurous habits—especially for children.

Jason is also a passionate cook. For him, the outdoors isn’t just about where you go—it’s about how you live when you get there. His favorite part of vehicle-based adventure travel (aside from the journey itself) is camp cooking: finding ways to translate comforting home-cooked meals into simple, delicious, dishes that can be made over a fire or in the camp kitchen. Food is a catalyst for connection, and Jason uses it as a way for families to unwind, slow down, and share memories around a camp table.

Now based in the Chicago area, Jason spends his time exploring the Midwest with his wife and young son, often traveling in “Chuck,” the family’s 1991 Toyota Land Cruiser FJ80 and the flagship build of Outland Club. Through every trip, meal, and trail, Jason is driven by a single belief:

If kids fall in love with adventure early—and with comfort and confidence—they grow into adults who seek out wild places, protect them, and pass the love of exploration forward.

Outland Club exists to help make that future possible and help create our next generation of overland and adventure travel explorers.