In this episode, Taylor Baker sits down with Tim Stay, CEO of the Other Side Foundation, to discuss how the organization helps people break cycles of addiction, incarceration, and homelessness through peer-led community, work-based learning, and whole-person transformation.
What You’ll Learn
- Why lasting recovery and reentry often require more than treatment especially when people have spent years cycling through addiction and incarceration.
- How a long-term, residential model can rebuild daily habits, accountability, and practical life skills for sustainable independence.
- What it means to run a “peer-led” organization, and how leadership from lived experience changes culture and outcomes.
- How “perceived similarities” create hope when students can see someone like them leading, thriving, and proving change is possible.
- How social enterprises can serve a dual purpose: funding the mission while teaching real-world employability and teamwork.
- Which reentry barriers (like GED completion, driver’s license restoration, and job readiness) must be addressed to make change stick.
- How nonprofit marketing often needs to speak to two audiences at once: recruiting people who need services and attracting customers to mission-driven businesses.
- How simple AI tools can accelerate communication and content production for teams rebuilding skills and why leadership development is the biggest lever for scaling to new cities.
Tim’s story highlights what can happen when entrepreneurial discipline is paired with deep human commitment: a model that treats personal change as learnable, community-supported work, and then builds systems leaders, businesses, and long-term housing pathways that make that change repeatable. The conversation underscores that investing in people is not only the mission, but also the strategy that enables growth and wider impact.
To learn more about Tim Stay and their work, visit theothersideacademy.com.