Jen Loving with Jeff Olivet: What Actually Works in Solving Homelessness at Scale

Jen Loving, CEO of Destination: Home and one of the nation’s leading voices on homelessness systems change, joins host Jeff Olivet — nationally recognized homelessness policy expert, former Executive Director of the U.S. Interagency Council on Homelessness  — for a conversation grounded in what it actually takes to reduce homelessness at scale. With more than two decades of experience across government, nonprofit, and philanthropic sectors, Loving has helped lead some of the most ambitious housing and prevention strategies in the country, including large-scale investments in affordable housing and data-driven approaches to system design.In this episode, Loving reflects on the real drivers of homelessness and the persistent gap between public perception and lived reality. She discusses why “Housing First” has become a foundational approach, how public-private partnerships can unlock meaningful progress, and what cities often get wrong when trying to address the crisis. Drawing on her work in Silicon Valley, she offers a pragmatic view of what systems-level change looks like in practice and where measurable progress is being made.Together, Olivet and Loving explore the challenges of leading in a space where success is often slow, complex, and difficult to measure. The conversation examines how leaders build trust across sectors, sustain momentum despite setbacks, and remain focused on sustainable solutions in one of the country’s most urgent public policy challenges.