This document describes the OpenStack Korea User Group's efforts to establish an upstream contribution mentoring program. It details how they struggled at first due to a lack of experience, but were eventually able to contribute by starting small, such as adding columns to the OpenStack client output and fixing test cases. Over two years, they developed a contribution academy program where mentees analyzed the OpenStack client code, mapped out unimplemented commands, and implemented some themselves. As a result of this ongoing mentoring effort, they have contributed several bug fixes, issues, new commands, and documentation improvements to the OpenStack upstream project.