Gary and the crew head to Detroit to talk to Tawny, who started "Pink Pump," a trendy boutique that's dressing and accessorizing fashionista throughout southeast Michigan. Then they make their way to Milwaukee to meet with Ian and Jason, who created "Newaukee," a social media site that's helping young professionals to connect and explore all that Milwaukee has to offer. And last they venture to Chicago, to chat with Chastity, the founder "Urban Fit Clubs," a network that provides its members with access to a number of Chicago's best boutique fitness studios.