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 & President

Andrae Bailey is the founder and president of Rethinking Homelessness.

A veteran of more than 20 years in the field of social innovation, Andrae has advised and partnered with some of the most successful organizations in the United States to address deeply entrenched societal problems like homelessness.

Prior to the launch of Rethinking Homelessness in 2016, Andrae served as president and chief executive officer of the Central Florida Commission on Homelessness. And because of the results Andrae was able to produce for his community, he was appointed by Governor Rick Scott to the Florida Council on Homelessness. He was also selected by the Orlando Sentinel as the Central Floridian of the Year and was named one of the “50 Most Powerful People in Orlando” by Orlando magazine. Andrae’s work on homelessness was described as “historic” for President Barack Obama’s homelessness czar.

Andrae graduated from Heritage University and Seminary, where he received a master’s degree in pastoral theology. He also completed the Crummer Graduate School of Business mini-MBA program at Rollins College, and he is an instructor at the Edyth Bush Institute for Philanthropy & Nonprofit Leadership. Andrae is recognized by Certified Fund Raising Executive International as a certified fundraising executive (CFRE).




At Rethinking Homelessness, formerly known as Lead Homelessness, it’s our mission to help tackle some of your community’s most pressing homelessness-related issues. Please see the links below to learn how we’ve helped transform the landscape of homelessness across America, one city at a time. 

"EDITORIAL: Solving the stubborn panhandling problem"

(The Freelance Star)


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