Dilbert
The Takeover
S1 E4:
When Dilbert discovers Wally reading Dogbert's investing book, the two get involved in an elaborate stock buying charade orchestrated by Dogbert, and wind up owning a controlling interest in their own company. Wally and Dilbert attend a board meeting, where the board members attempt to determine how to lose more money and Dogbert becomes CEO. Dilbert proposes the idea of flex-time, where employees make up their own schedules. This causes a mass exodus form the workplace and the company loses all its money. Wally sells both his and Dilbert's stock before the prices go back up, so they are left with nothing, unlike Dogbert, who now owns the company.