Stop & Talk

Gil Alvarado is the Chief Financial and Investment Officer (CFIO) of the Prebys Foundation, where he helps steward a $1.2 billion portfolio with an eye toward both strong returns and strong community benefit. A national thought partner in mission-aligned investing, Gil brings an entrepreneurial mindset to philanthropy—designing funds, partnerships, and investment strategies that help fuel innovation, expand opportunity, and strengthen San Diego’s long-term resilience. 

This Episode: 

How can a foundation use the full breadth of its resources to support a thriving region? 
  

Grant and Gil unpack how the foundation’s investment strategy works in tandem with its grantmaking to advance health, creativity, and economic opportunity in San Diego. Gil explains how the $50 million Prebys Venture Fund backs early-stage life science and tech companies; why investments in affordable housing, small-business lending, and civic revitalization expand what’s possible for the region; and how patient capital (long-term investment) lets a foundation take the long view on challenges like climate resilience and the blue economy. 

This episode offers an accessible look at how financial strategy, mission, and community well-being intersect. 

Key Moments 

• [0:57] What impact investing means at Prebys 
• [3:44] Inside the Prebys Venture Fund and its early investments 
• [7:30] Using capital to expand affordable housing and small-business access 
• [24:16] Why integrating impact into investing is still rare—and what’s changing 
• [42:20] Why even a “small” portfolio can catalyze big change 

Resources  

Walking Shield has spent nearly four decades improving quality of life for Native communities across the United States—bridging sovereign tribal nations with philanthropy, federal agencies, and the U.S. military.  Alongside the Walking Shield team, Executive Director, Dr. John Castillo, and Senior Fellow, Mariano Diaz help tribes build the capacity needed to secure federal funding, strengthen infrastructure, and advance true self-determination. Their work blends grassroots trust-building with systems-level strategy, supporting tribes on projects ranging from road repairs and water access to energy development, environmental co-management, and leadership planning. 

This Episode:
What does true collaboration with tribal nations require? 

Dr. John Castillo and Mariano Diaz highlight the deep assets that guide Native communities, including long-standing governance traditions, cultural and environmental knowledge, and a strong commitment to collective well-being. They share how Walking Shield helps tribes use these strengths to access federal resources, plan for long-term development, and steward land and water. They also discuss the systemic barriers tribes still face, such as underinvestment and complex federal requirements, and how capacity-building can make a meaningful difference. 

Together with Grant, they explore San Diego’s uniquely rich tribal landscape, the growing promise of co-management of natural resources, and why trust, relationship-building, and listening first are essential for any partnership with Indian Country. At its heart, the conversation offers a long view of resilience and strategy, reminding us that when Native leadership is honored and communities have the tools to act on their priorities, progress becomes both possible and lasting. 

Key Moments: 

• [9:40] San Diego has the most tribes per capita and what that means for the region  
• [14:02] The capacity gap: why many tribes can’t access federal funds designed for them  
• [16:34] Everybody benefits: how the National Guard helped rebuild dangerous reservation roads  
• [34:10] Co-management, water rights, and environmental stewardship  
• [51:15] What partnership looks like when it works  

Resources Mentioned: 

Brandon Steppe left a corporate career to start a recording studio in his garage—never imagining that a few persistent neighborhood kids would change his life. Those early studio sessions grew into the David’s Harp Foundation, a nonprofit where justice-involved and opportunity youth in San Diego discover their voices and chart a path forward through music, media, and mentorship. 

This Episode

Can rhythm and relationship change a young person’s life? 

Brandon shares how vulnerability and honesty became cornerstones of his organization’s culture, starting with a simple practice he calls flashlight first: mentors shine the light on themselves before asking youth to open up. From those early lessons grew a creative community that helps youth connect to support, record songs behind detention walls, and build micro-enterprises that pay real wages and teach real skills. 

Together with Grant, Brandon explores how art heals, how relationships transform justice, and how community-rooted workforce programs can help young people thrive. 

Key Moments: 

• [4:05] How one determined teenager changed Brandon’s path 
• [8:28] “Flashlight first”—earning trust through vulnerability 
• [22:54] The importance of relational support 
• [32:52] Creating access and opportunity in the creative economy 
• [43:35] Turning a $1M gift into transformational community-based housing 

Resources Mentioned in This Episode: 

Richard Tate is the President and CEO of the California Wellness Foundation, where he leads with clarity, courage, and hope. A communications strategist turned first-time CEO, Richard embraces the power of philanthropy not just to fund change, but to stand up for values. Under his leadership, Cal Wellness has become a bold voice for health and racial justice at a time when those commitments are under attack.

This Episode: 

What does it mean for foundations to step out from behind the desk and lead with courage? 

Grant and Richard explore why this moment calls for philanthropy to mobilize more than just dollars—to use its voice, influence, and resources in defense of equity and community well-being. Richard shares what it’s like to lead through fear, why Cal Wellness is “spending up” in response to urgent need, and how hope remains a discipline for leaders navigating turbulent times. Along the way, he reflects on lessons from his parents, the Civil Rights Movement, and peers who inspire him to push beyond comfort zones. 

From navigating attacks on diversity and equity to reimagining healthcare in California, this conversation is a call to speak out, act boldly, and build a healthier, more just future together. 

Key Moments: 

• [5:18] Why leadership in philanthropy requires courage in polarized times 
• [10:01] Using influence and access: how CEOs can open doors for community voices 
• [24:36] Lessons from past movements that fuel courage today 
• [42:08] Why civic engagement and democracy are health issues  
• [47:38] What community organizations are teaching foundations about resilience and rebuilding 

Resources Mentioned: 

Scott Lewis is CEO and Editor-in-Chief of Voice of San Diego, the pioneering nonprofit newsroom he helped build nearly two decades ago. What began as an experiment in funding professional journalism outside of the old newspaper model is now a national template, proving that communities can sustain independent, fact-driven reporting. Scott is known for his candid, conversational style and his conviction that journalism is about creating a shared story that helps communities face hard truths and imagine better futures.

This Episode: 

What role does local journalism play in sustaining democracy and helping communities rise to their challenges? 

In this thought-provoking conversation, Scott and Grant trace the story of Voice of San Diego from its early days as a bold experiment to its present role covering the region’s toughest issues—from homelessness and housing to infrastructure, schools, and civic leadership. They explore how journalism can cut through partisanship and apathy by telling stories that matter, how San Diego’s unique civic culture shapes progress (and stalls it), and why shared stories are essential to purpose and belonging. 

Scott also reflects on the responsibility of local media in a time when national trust is fractured and public funding for journalism is under attack. For him, it comes down to optimism: believing that communities are strong enough to face their biggest problems when they have the facts and the courage to talk about them. 

Key Moments: 

• [4:28] How San Diego became a model for nonprofit local journalism 
• [9:08] Why Voice chose a candid, conversational style over traditional news “voice” 
• [13:00] The impact of federal cuts to public media and what it means for NPR, KPBS, and local outlets 
• [23:00] The challenges San Diego faces—housing, schools, homelessness—and why naming problems is an act of optimism 
• [38:18] Why journalism is a “tiny investment” with massive community returns 

Resources Mentioned in This Episode: