Leap Year (2011 - 2018)

Jack, Bryn, Olivia, Derek and Aaron face uncertainty about their future as CEO, Andy Corvell (guest star Craig Bierko) calls an all-hands meeting. With lay-offs looming, tensions rise and the group wonders, if they do get fired - what's next?

Newly laid-off, Jack, Aaron, Derek, Olivia and Bryn are recruited to participate in a mysterious business contest with a $500k prize. In the meantime, Jack tries desperately to convince popular novelist, Scarlett Lane to be his first client.

Jack's business relationship with his only client, novelist Scarlett Lane moves from professional to sexual. In the meantime, Olivia, struggling to find any client, hires Jack to help her market her only product -- herself.

Olivia tries to decide whether betraying her close friend, Aaron is worth a potential boost to her personal business.

The office server goes missing and Bryn faces a crisis of conscience and identity. Aaron, furious over Olivia's and Jack's betrayal, unleashes the full fury of a financial analyst.

Derek (Wilson Cleveland) gets slapped with a lawsuit and seeks help from attorney Josie Lanning (guest star Julie Warner). Jack loses his only client and most of his friends. Also guest starring Teri Reeves.

Jack has a plan to win the contest and save his friends' businesses. The problem? No one trusts him, no one likes him, and "friends" has become a very loose term.