The show opens with a short parody of the Disney short Feast entitled "Fat." Santa's Little Helper is fed scraps from the Simpsons' dinner table until he gets too fat and dies. He goes to Heaven and God offers him a choice between Fit Dog Heaven and Fat Dog Hell. Fat Dog Hell flashes a "Free Pizza" sign and Santa's Little Helper runs inside.
As the episode begins, Homer Simpson is watching TV when he sees an advertisement for a self-lifting chair. He gets interested in buying it, but it costs $1,100. Homer goes to Moe's Tavern to get some ideas to raise money. Lenny and Carl give him the idea for crowdfunding. He records a failed video for a website, which moves almost everyone in Springfield, so he gets enough money to buy a chair in almost no time.
Meanwhile, at Springfield Elementary's club sign-up day, Lisa Simpson is trying to get signatures for The Magic Club, where she first meets Harper Jambowski, who appears interested in joining the club, because it was the only one that doesn't creep her out. Lisa shows interest on her new friend, discovering that she's also a pretty talented magician. When the Springfieldians realize that their money was spent on such a useless item like the chair, they form a mob and go to the Simpsons' house to burn the chair down. At night, Homer gets angry about the chair, complaining that he never gets the finest things in life. That's when Lisa asks him to take her to an Australian boy band concert with Harper, as her father has bought the seats. Feeling confident, he takes Lisa to the show.
At the sports arena, Homer gets surprised as he's given platinum with stripes VIP wristbands. That's when he first meets Harper's dad and discovers that they also have a lot of things in common and that Harper's father is extremely rich from his IT company. On their way back home, Lisa complains about Harper didn't let her say a word at the show, so Homer tries to convince Lisa to keep her as her best friend, because that way Lisa will enjoy the many great things in the world that Homer can't afford (namely, all of them). Harper then invites them to see a David Copperfield presentation. At the show once again, Harper doesn't let Lisa participate while their fathers are enjoying themselves. Lisa becomes more disenchanted with Harper, but Homer remains good friends with Harper's father and gets an invitation for the Simpson family to spend a week at their private island. They originally think they can't go because it's a school week, but Principal Skinner calls the Simpsons saying that school next week has been canceled (he received a whopping $10 bribe from Harper's father to make that happen).
Later, Harper gives Lisa a gift: a new bicycle. Lisa, though, has become fed-up with Harper and takes the bike gift as an insult because she likes her current bicycle (Harper doesn't help by saying Lisa's old bike is "crappy") and feels it's another example of Harper wanting to control everything around her. They argue to the point of mutually ending their friendship, but Lisa once again decides to go along with being around for her dad's sake, so they could go to the island. At the private island (which was formerly Haiti), the family's fun is ruined when Harper and Lisa fight once again. Homer must make a hard decision: continue being friends with Harper's father or go home so Lisa can get away from Harper. He decides to leave the island and go home, saying that Harper is "kinda spoiled" and that she doesn't deserve Lisa.
During the credits, Homer and Lisa are on the airplane back to Springfield as he says goodbye to everything on that island. Homer and Lisa then notice that Bart is still on the island as he has spelled out the message "So long suckers" on the shore.