Nathan Flomm (Larry David) is a marketing executive who sells his shares in an electric car company that is on the verge of going public, then becomes a laughing stock when the company enjoys huge success. To hide from the hordes of people who mock him for losing out on billions of dollars, he moves from California to Martha's Vineyard and changes his name to Rolly DaVore. He manages to build a quiet life over the next decade, working as a carer for an elderly woman and generally being a pillar of the community, but his tranquillity is shattered when his former business partner Will Haney (Jon Hamm) arrives on the island with his new wife Rhonda (Kate Hudson). Rolly very quickly decides that this is the perfect opportunity to wreak vengeance on the man who cost him a fortune.