Rethinking Homelessness is a social innovation organization established in 2016 to help community leaders find real and lasting solutions to one of America’s most persistent social problems. For more than 20 years, the members of our team have been leading or partnering with some of the most successful organizations in America that are working to solve the problem of homelessness.

Our work with homelessness began right here in our hometown of Orlando. When we assumed responsibility for finding solutions to homelessness in our community, Orlando had just been designated by the U.S. Department of Housing and Urban Development as the number-one mid-sized city in America for chronic homelessness, and the city was ranked in the top four in every category of homelessness measured by the federal government. But in just 36 months, we led a collective effort that reduced homelessness in Orlando by 60 percent, prompting the federal government’s homeless “czar” to describe our results as “one of the more astonishing transformations I have seen in my career.”

We have succeeded where others had failed because we are committed to finding a collaborative approach to the problem and to implementing the national “best practices” we had gathered from communities across America with track records of success. With the goal of ending homelessness in mind, we bring together elected officials, business executives, faith leaders, and concerned philanthropists and nonprofit leaders to create a consensus strategy for significantly reducing homelessness in Orlando. Then we fund and implement that strategy to produce unprecedented results.


Andrae Bailey
Founder & CEO
Nick Henry
Consultant & Project Manager
Madison Rubert
Director of Partnership Development
Amber Addario
Director of Compliance & Finance
Matthew Nagle
Creative Director


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