Stemming from the Next Gen episode "Coming of Age", this term refers to the character Jake Kurland, who was a teenaged friend of Wesley's (The Boy?) aboard the Entrepreneur. After failing to gain entrance to the Starfleet Finals exam, Jake freaks out and rashly absconds away in a Previa, only to soon panic and have to embarrassingly rely on Picard's guidance to get the shuttle back safely.

Ben and Adam have since immortalized Jake's actions into a full on podcast term, referring to any instance of spacecraft thievery or other such behaviors as "Jake-ing".

Jake Kurland in stolen shuttle

Jake in the act of Jake-ing a Previa for his misguided Jake plans