Russ wants to secure a new route to the hot party destination of Iceland, for Trans Alliance Airlines. Sam eagerly takes on the task of impressing his new Icelandic friends, but when it appears that his generous token isn't as impressive as he thought, he's forced to hang out with young Icelandic executive Harald in order to get company information from him.
Russ totals Sam's car in the company parking garage and rushes to cover up his crime and ease his guilt by lending Sam his motorcycle and sending him on a first-class business trip to Hawaii. After Sully ends up destroying Russ' motorcycle, Sam is desperate to come up with the money for the repairs and enrolls in a drug trial that sends him on a real trip.
When Russ tells everyone not to give him gifts for his birthday, they know he doesn't mean it, so they scramble to get him the most expensive and elaborate gifts they can find. Sam finds out that Russ once owned and loved an exotic bird, so he sets out to get him one for his party. Of course, nothing Sam does ever goes smoothly, and he gets into hot water for rushing his gift across international borders.
When Russ wants to attract more families to TransAlliance Airlines, he asks his team to create a fun and original icon for the kids. Sam submits an original idea from Darcy that Russ initially loves. However, when Russ mistakenly sees a doodle that Sully had drawn, he trashes Darcy's idea and goes with Sully's. But like everything Sully does, it creates even more problems than it's worth.
Sam is invited to a business lunch with Russ and all of his friends from the other airlines. However, being part of the big boys' club isn't as easy as it sounds. When Sam's donation to The Dutch's charity takes him on a trip he'll never forget, it also ends up costing him more than he bargained for.
Sam doesn't understand why Meryl is so angry at him for nominating her for a prestigious award that's only for female executives. However, after he accidentally discovers that Meryl has a much bigger ego than he previously thought, he's forced to face her man-to-man.
Russ has to take drastic measures to keep TransAlliance in the black and asks his team to take on a corporate sponsor. When Sam is assigned the task, he initially resists because he feels they are selling out.
When Russ' dearest friend Crazy Goat dies, Russ asks his staff to come up with crazy ways to make the company money just like Crazy Goat would. Sam asks Derek Tricolli to set up a meeting to discuss a lucrative business merger involving his company and the airline.
After Sam's meeting with the American Association of Plus-Sized Adults goes terribly wrong, he is forced to wear a fat suit on a Trans-Alliance flight. Flying coach, Sam finds himself seated next to Dallas Maverick's owner Mark Cuban. Russ has given Sam an additional assignment on the flight- to spy on his girlfriend to make sure she isn't cheating on him. What Sam doesn't realize is that Russ has ensured there isn't any wiggle room for error.
Sam easily turns down Meryl after Russ' good friend Ralph, a legend in the airline industry, offers to help him on a new project. When the project ends up becoming a circus, Sam begs Meryl to take him back but she's not one to forgive that easy.