 Adopted into the Chaya family, he established a humble business in Kyoto making drapes.He developed a strong business relationship with one of his clients, Matsudaira Hirotada, and later sent his son Chaya Shirōjirō Kiyonobu to Mikawa province to serve as a squire to Hirotada's son, now known as Tokugawa Ieyasu

Kiyonobu thus became one of the primary suppliers of the Tokugawa family, and quickly came into great wealth and influence in Kyoto.He accompanied Ieyasu in battle, at both the Mikatagahara (1573), and served him in other ways, as an intelligence agent in Kyoto and in secretly transporting messages and goods for Ieyasu during the time when Toyotomi Hideyoshi held power.