A father takes his son to tour colleges on the East Coast and meets up with an old friend who makes him feel inferior about his life's choices.

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 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%..

Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives.