Bailey was born and raised in New Jersey, where he developed an eye for the cinematic beauty hidden within an often-overlooked state. He moved to Boston to study Visual Media Arts at Emerson College before moving to Los Angeles to pursue filmmaking. Bailey moved back East to pursue family and set up shop in Portland, Maine.

Through documentary, commercial, and corporate work, Bailey honed his vérité style. He also developed an expertise in drone cinematography, operating everything from dual-controlled cinema drones to agile FPV racers. His in-the-field experience over the past decade has led to collaborations with National Geographic, 60 Minutes, LEGO, the Aquarium of the Pacific, Goldman Sachs, and more.

Bailey is also an avid backpacker and explorer.