When Richard meets an interested investor with a sketchy past, he must weigh his integrity against a tempting financial offer. Jared seeks a new future, putting him at odds with Richard. A defiant Gilfoyle butts heads with HR over his lack of direct reports. Hoover and Denpok worry when Gavin explores alternative solutions to keep a leaner Hooli afloat.

Richard's authority is threatened by his former Hooli manager; Monica tries to prove her support of other women; Gavin sets his sights on the literary world.