Marty's newfound optimism is rocked when Kaan & Associates receives a serious legal blow, while Jeannie attempts to rectify the situation; fearful she is the one responsible for it. Roscoe finds a constructive outlet to help work through his relationship issues.

Emotions run high as Marty and Jeannie deal with the aftermath of a tragic event and Marty questions his friendship with Dre. Doug experiences side effects from W.O.N. that may mean trouble for Monica¿s new company. Meanwhile, Doug attempts to reconcile with Sarah, and Marissa makes a business decision that affects her relationship with Clyde.

Jeannie reaches out to an old friend for help with a government contract, causing an issue between her and Marty about their future with Dollahyde. Clyde creates friction between Monica and her client, Vincent; and Doug makes a play for Caitlin.

Marty and the Pod accompany Lukas on a tour through his old neighborhood. Monica seeks help from Kaan & Associates on a new food product. Roscoe is embarrassed by Lex.

Marty and the team execute a plan to wrestle Marissa's family's media company away from her siblings. Jeannie encourages Marty to let Clyde out of the doghouse. Doug and Sarah's relationship is tested.

Marty and Jeannie have different approaches on how to deal with Lukas' attempts to sabotage DollaHyde. The relationship between Roscoe and Lex becomes a problem for Marty.

At the DollaHyde sneaker launch party, Marty is tested by Dre and considers a double cross. Meanwhile, Jeannie learns that Lukas has become suspicious of their plan. A displaced Clyde tries to make headway with Marty, while Doug makes a fatal mistake.

Marty and Jeannie launch a duplicitous plan to remove Lukas from DollaHyde. Dre and Marty continue to bond on a personal level. Clyde woos Marissa, a big client, to bring to Kaan & Associates; and Doug deals with his feelings about having a baby with Sarah.

Marty deals with his newest clients, hip-hop clothing moguls Dre Collins and Lukas Frye, who have divergent attitudes and plans for their company, DollaHyde. Jeannie defines the role she'll play in her new position. Clyde goes through some personal hard times and turns to Marty for help.

Marty and Jeannie put their plan into action to pit rival clients against one another, but things do not go as smoothly as planned. Changes at Galweather promise trouble for Jeannie. Clyde's already difficult work situation under Monica becomes even more brutal when he is forced to work from her home.

Marty has a confusing meeting with Roscoe's new crush, Lex. Jeannie makes some power moves at Galweather Stearn to win an account with the Department of Defense. Sarah announces to Doug she wants them to have a baby, and Clyde witnesses Monica push a junior analyst a bit too far.

Marty and his new Kaan & Associates pod pursue an organic grocery store CEO. Jeannie endures Doug's reminiscing about the "old team," while expressing his dislike for their new co-workers at Galweather Stearn. Meanwhile, Clyde struggles in his new position working for Monica, who is a far more heinous boss than he could have imagined.