Josh Caldwell quits his corporate job and decides to cross the United States on a Segway, from Seattle to Boston, and Hunter Weeks quits his own cubicle job to film the whole thing. The film is a road trip shot from a machine that tops out around ten miles an hour, which means every gas station, motel, and stranger's driveway becomes part of the story instead of scenery to blow past. Weeks catches the mechanical breakdowns, the sore muscles, and the moments where the pair debate whether the whole plan was a mistake, alongside the small-town encounters that only happen when you're moving slow enough for people to flag you down and ask what you're doing. The tone stays comedic rather than solemn: two friends narrating their own bad decision in real time while it turns into something that actually works. It was promoted as one of the first feature-length documentaries released on YouTube, and its subject is less the Segway than the leap from a steady paycheck into a plan with no guaranteed ending.