Richard butts heads with Dinesh, whose new position goes to his head. Richard discovers interesting data about PiperChat’s users. Erlich makes a play to be involved in Jian-Yang’s new app. Jared sets ground rules in his friendship with Richard. Gavin’s paranoia over Jack’s enthusiasm causes him to make a rash decision.

An overtired Richard pushes himself to the brink of sanity while trying to move ahead with his next big idea. Eyeing a comeback, Erlich pressures an uncooperative Jian-Yang. Monica sets a trap at Raviga to improve her standing with Laurie. Dinesh goes on a date. Big Head enters the world of academia. Gavin faces an unknown future.

When Richard reaches out to an unlikely ally, Jared worries about the company he's keeping. Gilfoyle gets tough on security in the wake of Dinesh's latest dalliance; later, he considers whether to put his pride aside for a job. Concerned about Jian-Yang's commitment to his app, Erlich takes matters into his own hands.

Richard meets a potential investor. Gilfoyle butts heads with HR. Gavin explores a leaner Hooli's future.