Shin'emon hired Konoha to help transport a supposedly priceless tea cup called Kachoufuugetsu (Beauty of Nature) to an exhibition. Turns out he was kind of a jerk about it—the guy valued that cup way more than the lives of Naruto and Kiba, who'd shown up to help. When bandits made off with it, all three went after them. Shin'emon fought the bandit leader solo to reclaim it, but the guy decided to bring the whole cave down rather than lose. The cup went over a ledge and shattered on the rocks below, and Shin'emon followed it over the edge.
Falling, he had time to reflect on what a terrible person he'd been—and was genuinely shocked when Naruto caught him and pulled him back up.
They reached the exhibition empty-handed, but Shin'emon had a realization. He could just make another tea cup. The real priceless treasure, he realized, was his own life—and honestly, he'd probably create an even better vessel next time anyway. It's a bit corny, but the guy actually learned something.
Content compiled by AnimeList.moe from publicly available sources.