1994 - Winning Futures was founded by Sam Cupp, a successful entrepreneur, in the Warren Consolidated School District in Warren, Michigan. Sam’s illustrious career began with the help of a teacher, a counselor, and a businessman working together for the best interest of their student. In turn, he wanted to give back to his community and created a program that could initiate this type of partnership for students.
 1998 – Sam’s first mentee in Winning Futures, Kristina Marshall, was hired by the program and is now its president and CEO.
2003 – Winning Futures founded the Metro Detroit Mentor Collaboration (MDMC) to aid Southeast Michigan mentoring programs in reaching their greatest potential by partnering veteran programs with new initiatives. The MDMC meets bi-monthly to discuss ways to improve, enhance, and strengthen mentoring in Southeast Michigan. 2004 – Winning Futures expanded to the Oak Park School District through a partnership with the Oak Park Business and Education Alliance. 2004 – Winning Futures began selling its life skills workbooks and training guides to other mentoring programs and schools. 2005 – Winning Futures began operating school-based mentoring programs in the Highland Park School District in Michigan for elementary students. 2005 – Winning Futures began operating school-based mentoring programs in the Pontiac School District in Michigan for high school students. 2008 – Winning Futures has now impacted over 16,000 students and awarded $1.5M in scholarships for youth to continue their education!
2009 – Schools, mentoring agencies, and other nonprofit organizations throughout the country began implementing the Winning Futures Workbooks and Activities into their youth programs.
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