This spring, the Rancho Santa Fe Foundation brought together fundholders, experts, and community partners for a three-part series focused on one of the most urgent issues facing our region: homelessness.

Designed to deepen understanding and drive action, our Homelessness Prevention Series equipped our philanthropic community with the context and tools needed to support effective, upstream solutions. It has also resulted in an investment that will keep members of the most vulnerable population from becoming homeless.

Taking a Deeper Dive

Across three powerful sessions, we explored the full landscape of homelessness—from answering the questions who is homeless, why they are homeless, and what the current reduction efforts are, to what is working, and finally, what we can do together to prevent it.

Session One: The Facts on Homelessness

In March, we launched the series with a packed room and an eye-opening discussion moderated by award-winning journalist Lisa Halverstadt of Voice of San Diego. Panelists included:

• Tamera Kohler, CEO of the San Diego Regional Task Force on Homelessness
• Ben Schuster, board member of the Lucky Duck Foundation
• Michael Gentiluomo, program counselor at The Arrow House

The conversation quickly revealed the severity of the issue: for every 10 people housed in San Diego, 14 more fall into homelessness for the first time—many due to economic hardship alone. Particularly vulnerable populations include older adults, families, women, and youth. We heard powerful stories from individuals with lived experience that dispelled myths and opened hearts. Our philanthropic audience learned that nearly all unhoused individuals report a traumatic experience that led to their homelessness.

This session made it clear: the system is overwhelmed. There isn’t a one-size-fits-all approach to solving the complex crisis, and we must act upstream to prevent homelessness before it begins.

Session Two: What’s Working

In May, we reconvened to spotlight what’s making a difference. Lisa returned to help us examine three key strategies: prevention, diversion, and intervention, with insights from front-line practitioners implementing these approaches every day. Panelist included:

• Drew Moser, CEO of Lucky Duck Foundation
• Paul Downey, CEO of Serving Seniors
• Sofia Cardenas, Data & Compliance Manager of Alpha Project
• Carla Vanegas, Director of Outreach of San Diego Rescue Mission

The session illustrated how coordinated, data-informed strategies—especially those that prevent a housing crisis before it starts—offer the greatest return on investment, both in terms of impact and cost. Drew spoke to upstream prevention efforts that focused on vulnerable populations such as foster youth, who have a 30% chance of becoming homeless. Paul talked about more immediate prevention efforts such as subsidizing rent for low-income seniors who are the fastest growing demographic of the population who are becoming homeless. Sofia helped us understand what diversion is, how it works, and shared its impressive success. Carla took us through what street outreach looks like and how complicated it truly can be for an individual to exit homelessness.

Session Three: From Awareness to Action

Our final session in June shifted from learning to doing. We explored how philanthropy can lead the way in addressing the homelessness crisis, especially through prevention programs that keep people housed in the first place. The conversation was led by:

• Ben Moraga, CEO of Rancho Santa Fe Foundation
• Drew Moser, CEO of the Lucky Duck Foundation
• Edith Glassey, Chief Philanthropy Officer of Serving Seniors

A Real-World Impact: Expanding “Seniors Safe at Home”

This series didn’t just spark conversation—it sparked investment. In partnership with the Lucky Duck Foundation, we announced a $100,000 commitment from Rancho Santa Fe Foundation to expand the Seniors Safe at Home program, which provides shallow rental subsidies and case management to help low-income older adults stay housed.

The Power of Partnership

This commitment, matched by Lucky Duck Foundation and supplemented by additional philanthropic support, unlocked over $700,000 in funding to prevent homelessness among at-risk seniors.

Why this program? Because the data is clear: keeping a senior stably housed can cost as little as $250/month, compared to over $40,000/year in public costs for someone experiencing unsheltered homelessness. Keeping people housed is not only a smart economic decision. It supports better outcomes in physical health, emotional well-being, and preserves dignity. A societal shift to focus on prevention is humane and smart.

Where We Go from Here

At RSF Foundation, our Community Leadership work is about education and turning insight into impact. This series was created in response to our fundholders’ desire to be more informed, strategic, and connected as philanthropists. We will continue to monitor the homelessness crisis and uplift what is working. We will engage our partners to ensure that impact is being made, and we will continue to support our philanthropic fundholders in gaining the insights they need to be strategic in their giving. But we can’t stop here; to ensure no senior falls into homelessness, continued progress will require greater investment.

It Takes a Village

Thank you to our host committee, every speaker, partner, and fundholder who participated. And thank you to the many who have already stepped forward to support programs like Seniors Safe at Home. If you’d like to join our homelessness prevention initiative, we invite you to contact us at info@rsffoundation.org.

Together, we can create a region where fewer people fall into homelessness—and more can thrive in dignity and stability.