Behind The Sign

What started as an uncertain college project became one of Oklahoma City’s most successful social enterprises.

In Episode 3 of Behind the Sign, Whitley O’Connor shares how he and Ranya O’Connor launched The Curbside Chronicle with four vendors, two donors, and no guarantee that the idea would work.

Today, Curbside Enterprises creates employment opportunities through its street magazine, flower shop, apparel company, and youth programs. Its vendors and employees earned more than $1.1 million last year, while hundreds of people gained income, job skills, community, and a pathway toward stable housing.

Whitley explains:

• How selling a $2 magazine can help someone rebuild their life
• Why Curbside vendors purchase the magazines they sell
• The story of the first vendor Curbside helped house
• How Curbside Flowers grew from buckets of carnations
• Why employment requires more than simply offering someone a job
• The truth about addiction and homelessness
• How social enterprises can create lasting community change

Every magazine purchased begins with a simple interaction, but that interaction can lead to employment, stability, housing, and a renewed sense of belonging.

Learn more, shop, or support the mission at curbside.org.

Subscribe to Behind the Sign for more conversations that challenge assumptions and reveal the people behind the signs.

Do people living in homeless encampments actually want housing? Jamie Caves says 92% of the people offered housing through Key to Home’s Encampment Rehousing Initiative accept it.

In Episode 2 of Behind the Sign, Jamie joins Gary Brooks to explain how Oklahoma City is helping people move from encampments into housing. They walk through what it takes to close a camp, why clearing a site without a housing plan leaves the problem unresolved, and how outreach workers build the trust needed to help people move forward.

Jamie also shares the story of a man who was working full time while sleeping under a bridge. A short period of illness had cost him his housing, and one week after connecting with an early intervention specialist, he was back in an apartment.

The conversation covers the Virginia Avenue encampment, youth homelessness, mental health support, and practical ways the community can help. It’s a closer look at the people and work behind a problem many of us think we understand.

Learn more or find ways to get involved at keytohomeokc.org.

Subscribe to Behind the Sign for conversations that help us see the people behind the signs.

What if much of what we believe about homelessness is wrong?Rachel Freeman, CEO of City Care, joins Gary Brooks for the first episode of Behind the Sign to challenge common assumptions about homelessness and explain what actually helps people rebuild their lives.Rachel shares how losing her mother, being raised by her grandmother, and experiencing poverty shaped her understanding of community, faith, and what she calls “relational margin.” She also explains why homelessness is rarely as simple as personal responsibility and why even well-intentioned efforts can sometimes create unintended consequences.In this conversation:The biggest myths about homelessnessWhy more than 5,000 people experienced homelessness in Oklahoma City in 2025How low-barrier shelters help people move toward stabilityWhy relationships are essential to lasting recoveryThe difference between charity and genuine proximityHow churches can engage more effectivelyCity Care’s new medical respite centerWhy Rachel believes homelessness can be solvedBehind the Sign explores the people, systems, and stories behind homelessness while replacing assumptions with truth.Subscribe for honest conversations about homelessness, housing, community, faith, and the work being done across Oklahoma.