Chasing the America’s Cup was never the end goal for Santa Clara, California sailor Sean O’Halloran. Instead, it was about pursuing ever greater skills, experience, strength, and endurance any way he could. From bartending in Newport, to the proving grounds of Oakcliff, and then on to a shore team position at American Magic, his mindset was to finish each day as a better sailor than he was in the morning. In June 2019, Sean was offered a chance to step onboard DEFIANT as a member of the sailing team… but only if he could pass a test that few in the world would even attempt.

To earn a spot onboard an America's Cup boat, would you upend your entire life, home, and career, embrace years of training, sacrifice and uncertainty, have enough faith in yourself to pass one, final, decisive, grueling test... and then keep passing that test until the Cup is won?