Richard "Rick" Simmons II
Chief Executive Officer | Rebuilders Alliance
Richard “Rick” Simmons II is a seasoned real estate and finance professional, community builder, and faith-driven leader with more than 20 years of experience in real estate finance, brokerage, acquisitions, property management, construction oversight, and strategic development.
Throughout his career, Rick has helped individuals, entrepreneurs, and investors navigate the path from financial stability to ownership. His experience spans residential and commercial real estate, lending and financing strategies, property acquisition and development, business consulting, and helping clients structure opportunities that create sustainable growth and long-term wealth.
Today, Rick serves as Chief Executive Officer of Rebuilders Alliance, where he brings his professional experience into a broader mission of community restoration and economic empowerment. As CEO, he provides strategic leadership for an ecosystem designed to connect residents, businesses, faith leaders, professionals, and community organizations around pathways including housing and real estate, economics and business development, construction and skilled trades, education, technology, health and wellness, and civic leadership.
At the foundation of Rick’s leadership is his faith. He believes lasting community transformation requires more than programs and resources—it requires purpose, relationships, stewardship, and a commitment to serving people. Guided by the biblical principles of restoration and rebuilding found in Nehemiah, Rick is committed to helping transform collaboration into infrastructure and opportunities into measurable outcomes.
Through Rebuilders Alliance, Rick is using the experience gained throughout his career to help build something larger than any single organization: a connected ecosystem where people can move from stability to ownership, from opportunity to legacy, and from community challenges to community-led solutions.
Michael Davis - Crayton
Co-Founder of the Rebuilders Alliance
As a Co-Founder of Rebuilders Alliance, he is one of the driving forces behind a movement dedicated to rebuilding lives, restoring communities, and raising the standard of living for residents across Chicago's south side.
From the ground up, he helped shape the vision, structure, and mission of Rebuilders Alliance — creating an organization built on the belief that every individual deserves access to the resources, relationships, and pathways needed to reach their full potential. His leadership has been instrumental in establishing the 12 Paths of Development framework that guides everything the Alliance does.
He is a builder in every sense of the word — committed to creating lasting change not just for today, but for the generations that will inherit these communities. Through Rebuilders Alliance, he continues to pour into people, open doors, and ensure that no one has to walk their path alone.
Demario Ash
Chief Operations Officer | Rebuilders Alliance
WHERE VISION MEETS EXECUTION
DeMario believes in “servant leadership” with over twenty-five years of professional experience…while also assisting various ministries/organizations.
DeMario brings project management and sales expertise to Rebuilders Alliance, along with a Kingdom-minded approach. He has been ordained by two ministries: From the Heart Church Ministries Inc. (FTHCM), where he served as Youth Pastor and Licensed Minister, and The Gathering Place Worship Assembly.
DeMario also attended Moody Bible Institute (MBI) for two years in their counseling program gaining a deeper understanding of God’s word, mental/spiritual health, and the culture in which we live.
As the Chief Operating Officer his primary role is supporting the paths through collaboration within the ecosystem…taking the vision of RA as an idea and housing that idea in infrastructure.
Dana Simmons
Chief of Staff | Rebuilders Alliance
Dana Simmons is a woman of God, devoted wife, and mother with a passion for serving others through faith, leadership, and encouragement. She holds a Bachelor's degree in Business Administration and brings more than 20 years of experience in the health insurance industry, where she discovered her passion for training, mentoring, and developing people.
Throughout the years, Dana has mentored youth, taught Sunday school, and has become especially passionate about helping young women discover their God-given identity and walk confidently in biblical truth.
As Chief of Staff for Rebuilders Alliance, Dana helps drive strategic initiatives, align organizational priorities, and support the execution of the organization's mission. Through servant leadership, operational excellence, and a heart for people, she is committed to helping build stronger individuals, stronger families, and stronger communities.
Anwar Randle
Co-Director of the Civics Path
Anwar Randle serves as the Co-Director of the Civics Path at Rebuilders Alliance, where he leads initiatives that empower individuals and strengthen communities through civic engagement, leadership development, and grassroots organizing.
With a strong background in community advocacy, program development, and collaborative leadership, Anwar is dedicated to building informed, active citizens and creating pathways for meaningful change. He brings a hands-on approach to community work, meeting people where they are and equipping them with the tools and knowledge needed to become effective agents of change in their neighborhoods.
Anwar understands that lasting community transformation starts at the grassroots level. Through the Civics Path at Rebuilders Alliance, he works to bridge the gap between residents and the systems that shape their lives — fostering a culture of civic responsibility, collective action, and community pride.
He believes that when people are educated, engaged, and united, we can rebuild stronger communities and create a better future for generations to come.
Laurence Littleton
Founder & Executive Director, MAN, NFP
Path Director — Rebuilders Alliance
Laurence Littleton brings over 30 years of in-depth Information Technology and infrastructure experience to his work as a community leader, mentor, and Path Director with the Rebuilders Alliance. As Founder and Executive Director of MAN, NFP, he leads a structured leadership development organization serving men impacted by community violence and systemic inequities in Chicago.
He is the architect and author of MAN's CVI (Community Violence Intervention), Workforce Development, and Community Development curricula — organic, phase-based programs integrating character development, civic awareness, and technical skill-building designed to transform mindsets and foster lasting change for individuals most affected by systemic and community violence.
A Certified CompTIA A+ Instructor, Laurence has spent three decades helping organizations leverage technology, providing infrastructure support, and training others to build the same technical foundation that shaped his own career.
Laurence holds a Master's degree in Information Systems Management from Robert Morris University and is the author of aMErica: The Ultimate ME Society, a thought-provoking exploration of personal responsibility and societal growth, available on Amazon.
Laurence is committed to developing accountable leaders who strengthen families and rebuild communities.