San Diego native Robert Capita was once on track to be part of the US Olympic Sailing Team at the 1980 Moscow Summer Olympic Games until the US boycotted those Games. After that, Robert's life changed course when he decided to abandon sailing to take over his dad's business. However, his desire to race never subsided. Nominated by his son, Robert is given a second chance to pursue his dream job and is mentored by renowned and decorated sailor Gary Jobson for two grueling weeks. At the end of this journey, Robert is given the shot to become Captain of an America's Cup sailboat.