He grew up in San Jose, California, where he learned to sail at summer camp at around the age of 12. When he joined his college sailing team, the sport became a major focus in his life. He earned a spot on the team through countless hours of studying videos of sailing technique. After graduation, O’Halloran went into the culinary industry, but sailing was never far from his thoughts. In 2015, he moved to Newport, Rhode Island, where he managed a bar and continued to seek more sailing experience. He landed a ride on a J/122 for Block Island Race Week, where he first learned about Oakcliff Sailing and how its Sapling program could turn his passion into a profession. He applied and was accepted in 2016.