Meet Kicker. He's a second-generation bag maker who sells his Damn Dog line of premium men's handbags from his mobile home headquarters.

Tilman never shies away from a challenge so he's thrilled to take over driving duties from Kicker's girlfriend, Jenn.

When Tilman gives Kicker the chance to sell Damn Dog merchandise from one of his Bubba Gump Shrimp restaurants, things don't go well. They only sell one item.

Kicker cradles his dog Chewie while Tilman collects some information about Damn Dog from Kicker's parents and brother.

High five! No? Tilman leaves Kicker hanging after hearing his lackluster bid. Kicker is only willing to give Tilman a 10% discount. No deal.

Pop Brothers founders Octavio and Chuck, along with Octavio's wife Shannon, listen to Tilman after he comes to visit their organic ice pop shop in Mississippi.

Octavio steps away from the watermelon so that Tilman can get his hands dirty and see how Pop Brothers makes their tasty, artisanal ice pops.

Tilman allows Pop Brothers to offer its treats at his Golden Nugget Casino, and is impressed when they sell 112 ice pops in only two hours.

A determined Octavio drives through dangerous floodwaters in order to deliver a shipment of ice pops to Tilman.

Success! Tilman doesn't get the wholesale price he wanted, but is impressed by the team's dedication and works to make a deal happen.