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15 Episodes 2013 - 2014
Episode 1
Fri, Sep 27, 2013 60 mins
Season 5 begins with Twin Peaks CEO Randy Dewitt working undercover at his sports bar and grill. Later, former Hooters CEO Coby Brooks, now a Twin Peaks franchise owner, shaves his head and goes undercover as an inappropriate customer.
Episode 2
Fri, Oct 4, 2013 60 mins
Loehmann's CEO Steven Newman works undercover in the lingerie section of one of his discount department stores.
Episode 3
Fri, Oct 11, 2013 60 mins
Jane Grote Abell, chairman of Donatos Pizza, works undercover at her company.
Episode 4
Fri, Oct 18, 2013 60 mins
Anthony Wedo, CEO of Buffets, Inc., works undercover at his restaurants.
Episode 5
Fri, Oct 25, 2013 60 mins
Menchie's CEO Amit Kleinberger works undercover at his frozen yogurt business and delivers a baby calf while working as a herdsman at a dairy farm.
Episode 6
Fri, Nov 1, 2013 60 mins
Alfred Angelo president Paul Quentel works undercover at his bridal gown stores helping brides find their perfect wedding dress.
Episode 7
Fri, Nov 8, 2013 60 mins
Family Dollar president and COO Mike Bloom works undercover at his discount retail company and faces his fear of heights when he operates a forklift that takes him 35 feet into the air.
Episode 8
Fri, Nov 15, 2013 60 mins
Dutch Bros. Coffee co-founder and president Travis Boersma works under cover on a coffee plantation in El Salvador.
Episode 9
Fri, Nov 22, 2013 60 mins
Seven previously featured bosses discuss the challenges of keeping their undercover identity and provide updates on some of their memorable employees.
Episode 10
Fri, Dec 13, 2013 60 mins
Massage Heights COO Shane Evans tries to overcome her aversion to touching people when she works undercover as a massage therapist.
Episode 11
Fri, Jan 17, 2014 60 mins
Bruce "Two Dogs" Bozsum, chairman of Mohegan Sun, works undercover at his gaming, hotel and entertainment destinations, and prepares to pass the business onto the next chairman of his Native American Tribal Council.
Episode 12
Fri, Jan 31, 2014 60 mins
Joe DiDomizio, president and CEO of Hudson Group, works undercover at his travel retail company.
Episode 13
Fri, Feb 28, 2014 60 mins
Utah Jazz CEO Greg Miller works undercover during halftime of a game as part of the organization's dunk team.
Episode 14
Fri, Mar 7, 2014 60 mins
Three previously featured bosses each send an employee undercover to evaluate their companies. The CEOs are: Amit Kleinberger (Menchie's); Randy Dewitt (Twin Peaks); and Steve Greenbaum (PostNet).
Episode 15
Fri, Mar 14, 2014 60 mins
Sky Zone CEO Jeff Platt works undercover at his indoor trampoline park. He referees a children's dodgeball game and has trouble hiding his in-depth knowledge of the company while working in community relations.