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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. Only Tim McWinters (Tom Wilkinson) and Mike Pancake (Dave Franco) follow Dan. 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.
The three head to Portland, only for Dan to discover that Chuck is there trying to close a deal as well. She and Jim get along well, have worked together before and it appears as though she's been given the go ahead. Dan gives his presentation to Jim, only to faint in the middle of it. He makes Mike go finish, but everyone is distracted by Mike's last name. This forces Dan to scramble and find a way to get a step ahead of Chuck. Dan starts to lose faith in the team, as Tim is more concerned about finding a woman to make love with due to an unhappy marriage, and Mike never attended college while possibly being autistic.
Dan is told to go to Berlin to meet with Jim's parent department Gelger, specifically with Dirk Austerlitz. Dan travels with Tim and Mike and they go to find a client, Helen Harlmann, at a unisex bath house. He finds Helen with three other people. She doesn't trust him since he walked in there fully dressed in a suit. Dan undresses himself and gets Helen to listen to him, with Mike and Tim joining him despite him telling them not to.
Dan speaks to Bess, who had trouble at school, but he is unaware as to why and offers her heartfelt advice only to hang up and see Susan's emailed link which is to a video of Bess beating a kid up.
Mike finds a hostel for Tim and himself to stay at. Dan is in a room that is actually an exhibit called "American Businessman 42" in a museum, where everyone watches him. He starts to put some numbers together to outdo Chuck. Tim procures ecstasy from one of the youths staying the hostel. Tim and Mike follow him to find Bill in a gay nightclub during Filson Festival. Dan encounters Bill in a room with other men sticking their penises through glory holes. Bill later explains this is the only way he can get any sort of pleasure. He takes a look at Dan's numbers and says they definitely trounce Chuck's numbers. Dan and Bill also speak about how easy it is to get derailed from course.
The guys meet with Jim only to learn that Dirk Austerlitz is in St. Louis (the guys' hometown), annoying Dan. Jim later tells Dan that while his numbers are good, they aren't good enough to close the deal. The trio spends time with some of the youth at the hostel, being honest and smoking. After not smoking but listening to everyone, especially Mike, Dan goes out to buy "Straight Up Teal" eyeshadow and speak with his wife, his daughter, who reveals she beat up the other child for calling Paul names like "double stuff". Dan congratulates her but explains he will take care of Paul. He speaks with Paul and does his best to pick his spirits up. Dan later finds himself depressed and drinking with strangers/admirers of "American Businessman 42".
Dan awakes the next morning hungover. He joins the marathon and ignores an official's pleas for him to leave the race. Some of his "American Businessman 42" fans spot him and begin cheering him on with such enthusiasm it attracts the attention of a news caster. He finishes the race, poignant as he had trained for the St. Louis marathon.
Dan later manages to score a meeting with Dirk, via Bill. First, the guys pass through a riot going on outside the building where Austerlitz is located. After evading police and getting pelted with paintballs, the guys make it inside with the aid of Bill. Austerlitz likes what he hears from Dan, then what he sees on their front page, and they close a deal, thereby saving Dan's business. He, Tim, and Mike celebrate by gloating in front of both Chuck and Jim.
The guys return home to their respective loved ones. Mike rejoins his friends from the special home and boasts his multiple "explers" in Berlin. Tim reunites with the maid he encountered in Portland. Dan rejoins his family, now confident of their future.