A divorced, down-on-his-luck single father named Craig tries to apply for a loan to start a new business, but an encounter with an Australian Uber driver changes his life forever.

The South Florida Python Challenge begins. With $20,000 on the line, Craig decides to compete alone while Jillian scrambles to find a new partner.

Craig attends an entrepreneur conference to pitch his business idea to Rita Gaines; Isaiah tags along and creates some nuisance; Jillian sneaks in and pretends to be a wealthy businesswoman.

Craig and Jillian must team up with Brock to take down a mysterious rival who is running away with the competition.

Jillian gets a chance to live a fairy tale life when she takes a TaskRabbit job and house-sits for a wealthy woman named Sloane Faulkner. But things are not as they seem to be.

Suspicion lies heavy on Brock, Craig and Jillian, who are being investigated for their role in the mini golf shed burning down; Jillian faces the threat of deportation; Craig is forced to vote in the election by his daughter.