Amit Kleinberger, CEO of Menchie's, a popular frozen yogurt franchise, delivers a baby calf while working as a herdsman at a dairy farm. Also, the youngest Boss featured to date in the series goes deeper undercover when he dons a Menchie's mascot uniform at a kid's birthday party.

Mike Bloom, President and COO of Family Dollar Stores, one of the largest discount retail companies in the country, faces his fear of heights when learning to operate a forklift that takes him 35 feet into the air. Also, the boss nearly blows his rock 'n' roll disguise when one employee invites him to a jam session.