Richard Hendricks can’t have nice things. It’s not that he doesn’t allow himself to have nice things or even that he doesn’t want to have nice things, it is that he is almost karmicly incapable of having nice things. Through either incredible worry or the incredible stupidity of others, Richard is never allowed to be on unqualified winner. Part of this is due to Richard being an unconfident dweeb, but it is also due to the fact that Richard is the main character on a TV show and thus can’t be top dog for very long. Stories of winners constantly winning become boring because deserved success is boring. It’s fun to watch a single arc of a story be about winning (Friday Night Lights season one) but eventually that team has to start losing (Friday Night Lights season two). So, by the transitive property of TV trope math, because Richard Hendricks is a TV character, he can’t have nice things.
Read More about Silicon Valley, Ep. 2.08, “White Hat/Black Hat” doesn’t let Richard win