Brad Sloan (Ben Stiller) runs his own non-profit organization and lives a comfortable life with his loving wife and son, but cannot help contemplating how his old friends Craig Fisher (Michael Sheen), Billy Wearslter (Jemaine Clement), Jason Hatfield (Luke Wilson), and Nick Pascale (Mike White) are rich and accomplished. Craig works in the White House and has published a best-selling book; Jason owns a hedge fund firm; Billy sold a company he founded, moved to Maui, and retired; and Nick is a Hollywood director. Brad's wife, Melanie (Jenna Fischer), tries to comfort Brad, telling him that they do not need to compare themselves with the wealthiest 1%.