LeRoy L. Willis: Turning Pain into Property and Purpose for the Next Generations

A Kid Without a Home, Now Creating Homes for Others: LeRoy L. Willis is the Owner and Managing Broker of LWRealty, founder of LW Dream Appraisal, visionary founder of the LilBoyBigDreamz Academy Foundation, and a proud product of persistence, purpose, and faith.

This year, he is being honored with the Courage Award at the 2025 JoyTutor Celebrations of Courage Awards. With a deep passion for real estate and community empowerment, LeRoy has dedicated his life to transforming pain into purpose—helping families build wealth through real estate while mentoring the next generation of young Black men to believe in their dreams, no matter their zip code.

LeRoy Willis - Courage Award Honoree

Building Dreams from the Ground Up

From humble beginnings and housing insecurity, LeRoy has carved out a life anchored in service and legacy. Through his companies, he has helped clients achieve their real estate goals and built a trusted platform for aspiring investors and homeowners to grow their portfolios with confidence. Every home he sells, appraises, or develops is a part of his mission to empower others to own their future.

A Foundation for the Next Generation

His nonprofit, LilBoyBigDreamz Academy Foundation, is an extension of his soul work—created to uplift, educate, and inspire young men who, like him, have faced adversity. Through mentorship, access to resources, and real-life exposure to entrepreneurship, LeRoy creates a pipeline of possibility for boys who too often go unseen. His message is clear: no dream is too big, and no beginning too small.

Courageously Stepping Into a New Chapter

LeRoy’s journey is evolving with his new role at The TRECC Foundation, where he’s helping develop a historic facility designed to serve thousands across Chicago for generations to come. As a member of DB Capital, a real estate investing group, he is leading efforts to redevelop under-resourced suburban neighborhoods. With cameras documenting every move, their work will serve as a blueprint for transformation across America’s urban landscapes.

Honoring LeRoy’s Bold Vision and Fearless Leadership

At this year’s JoyTutor Celebrations of Courage Awards, we are honored to recognize LeRoy L. Willis for his relentless courage to rise above his circumstances and become a force for generational change. His life is proof that your past does not define you—your vision, resilience, and commitment to giving back do.