The undercover experience is no vacation for Stephen J. Cloobeck, Chairman and CEO of Diamond Resorts International, one of the world's largest timeshare companies, as he finds himself performing a dangerous job that bursts into flames. Meanwhile, the boss also reaches his breaking point with an employee's job performance, forcing him to break his cover.

Rick Tigner, President of Kendall- Jackson Wine Estates, causes a shutdown when he struggles to maintain pace on a bottling line, and is shocked by comments made by a delivery driver.