After an argument with his boss Chuck Portnoy (Sienna Miller) of Dynamic Systems, Dan Trunkman (Vince Vaughn) decides to leave and start his own business. Tim McWinters (Tom Wilkinson) who was fired for being too old and Mike Pancake who was there for an interview (Dave Franco) follow Dan and join his new company. A year later, Dan's business, Apex Select, has barely gotten off the ground. In a Dunkin' Donuts, Dan gets a message to go on a business trip to Portland to meet with investors Jim Spinch (James Marsden) and Bill Whilmsley (Nick Frost), the latter being a friend of Dan's. At home, Dan's kids Paul (Britton Sear) and Bess (Ella Anderson) are being bullied at school. Paul is ridiculed for his weight and attempts to wear eye shadow to fit in with the goth kids. Bess asks Dan to finish a homework assignment of hers that requires him to describe the kind of person he is. Dan's wife, Susan (June Diane Raphael), wants to put Paul in a private school, despite the pricey tuition, to bring him out of his shell..