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, Maine to meet with investors Jim Spinch (James Marsden) and Bill Whilmsley (Nick Frost), the latter being a friend of Dan's.