Frederick Enman, SJ, reflected on the future of the organization he founded over 30 years ago, Matthew 25, Inc. Known by many as “Father Fred”, his thoughts brought him back to the early influences in his life, especially around his vocation with the Society of Jesus (the “Jesuits”). In his early years he felt a call to live the message of the biblical passage of St. Matthew’s Gospel, Verse 25, about caring for others. He formed Matthew 25 with ninety dollars and a willingness to bootstrap its growth. He focused on housing for the poor. He became a mission-driven CEO and he learned how to lead through equal parts of trial, error, and creativity. To this 30 year point in time the work of Matthew 25 has created a one-by-one string of 12 homes that include a total of 20 housing units for at-risk families. Now, as he progresses through his senior years, Father Fred wondered what is best for the future of Matthew 25. He felt a sense of great gratitude for the numerous and varied ways so many people, organizations, and institutions worked collaboratively with him to achieve this growth, and wondered what it will take to lead Matthew 25 forward. The case is built from extensive interviews conducted with Father Fred based on the 30 year history of Matthew 25, Inc. Primary topics include the mission, formation, and leadership of the organization. Questions challenge case study students across various aspects of building and sustaining a mission-based non-profit, and more particularly, the leadership succession plan when the Founder/CEO reaches a retirement stage.