From Bar to Beach Concierge: Jenn’s OBX Hustle | #30

What do you do when the beach is your backyard—but you still need to pay the bills? Jenn Crossman carved out a life on the Outer Banks through grit, hospitality, and an entrepreneurial spark that led her from bartending to launching a bespoke concierge service. In this episode, Jen shares how she built a life around making visitors’ vacations unforgettable—from private beach dinners to dolphin tours and surprise engagements.

Takeaways:

• How living in a tourist town fuels creative side hustles

• Why great bartenders make natural connectors and entrepreneurs

• Insider tips on unique OBX experiences: Ocracoke, Manio, Duck, skydiving & more

Whether you’re planning your first trip or dreaming about making a coastal leap of your own, Jen’s story is a warm reminder that doing what you love and building community is possible—even on a sandbar.

Host: Randy Jones → @jonesgroupobx
Guest: Jen Crossman → OBX Travel Concierge