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- Season 14 overviewJan 4-Feb 16, 20159 episodesSeason 14 episodes1. May the Gods of Good Pies Be With Us Jan 4, 2015
- 16 celebrities are enlisted to create and sell pies in a competition for charity.—anonymous
- 2. Nobody Out Thinks Donald Trump Jan 5, 2015
- The teams write and produce a commercial; an insubordinate team member vexes a project manager.
- 3. A Family Affair Jan 12, 2015
- Project managers try to raise the most money for charity by selling wedding dresses.
- 4. I Wish I Had a Project Manager Jan 19, 2015
- Joan Rivers serves as a boardroom adviser as the teams prepare for an outdoor marketing event.
- 5. It's Like a Booze Cruise With Knowledge Jan 26, 2015
- Each team must plan and host an original boat tour of New York, with the guests choosing the winner.
- 6. Who Stole My Phone? Feb 2, 2015
- The teams are asked to create a "photo bomb" and a hashtag campaign; each team writes a jingle.
- 7. Top Feuds, Firings and Fails Feb 9, 2015
- Some of the best hirings and firings, feuds and the biggest mistakes.
- 8. Universal Wizards Feb 9, 2015
- The finalists travel to Orlando to complete their biggest task -- selling resort vacation packages.
- The two remaining finalists complete their last task; Donald Trump announces the season 14 winner.