Silicon Valley

Silicon Valley
Season 2, Episode 8
White Hat+Black Hat
Image #462 · 0:02

Source: Silicon Valley · S02E08 · White Hat/Black Hat · May 31, 2015

I think it's this.

TMDB episode metadata

Episode title: White Hat/Black Hat

Air date: May 31, 2015

Director: Alec Berg

Top billed cast: Thomas Middleditch, T.J. Miller, Zach Woods, Kumail Nanjiani, Martin Starr, Amanda Crew

Richard causes trouble when he sympathizes with a competitor.

Source: TMDB