Jeannie's boyfriend drops a bomb that could devastate her. Marty goes after potential new business at Doug's "Dungeons & Dragons" game. Clyde uncovers an issue that affects Jeannie.
When faced with the prospect of the ultimate buyout, Marty Kaan must decide: is it worth cashing in his chips and walking away -- or doubling down for the chance to pull off the deal of a lifetime.
Marty gets out of prison and does everything he can to rebuild his faltering consulting firm; Jeannie is pregnant with Marty's baby and trying to get back in his good graces after causing his downfall.
Marty slowly manages to get his entire pod back together at his new firm, but can they keep the business afloat?; Jeannie takes down Galweather & Stern and joins Marty in more ways than one.
Marty and the pod clash with the new CEO and Marty decides to open his own firm; Jeannie and Marty wrestle with their feelings for each other; Doug falls in love; Monica attempts to clean up her act.
Marty and his co-workers scheme to halt an unpopular merger between their firm and a former client; Jeannie struggles to balance her demanding job and her personal life; Marty and Monica spar over who will raise Roscoe.