After graduating from university, Kobayashi joined and worked there for 15 years. In part because the staid life of a bank employee did not suit him, while working in Osaka he was attracted to the literary and theatrical world. He spent more and more time in the entertainment district and got to know the men about town who were regulars there. The experience and connections that Kobayashi built up during this time would serve him well when he launched his theater group.