The Foundation

Upside on Stage at the 645 Ventures Annual Meeting
At the intersection of innovation and impact At the 645 Ventures Annual Meeting, Upside Founder and CEO Jake Rothstein joined a distinguished lineup of founders and investors under the theme “Building Generational Companies on the Edge of Innovation.” The session, titled “Trends Reshaping Healthcare: Innovation, Technology, and the Future of Care Delivery,” explored how leading Read More

Partnership in Action: Helping Virginia’s Most Vulnerable Find Home and Health
At Housing Virginia’s Most Vulnerable Conference, Upside’s Julie Isaacs joined Elizabeth Ramsey of Anthem HealthKeepers Plus to show what true partnership looks like in practice. Together, they illustrated how shared accountability, speed, and trust transform housing referrals into lasting stability for Virginia’s most vulnerable members. Housing Is Healthcare and It Works When We Work Together Read More

“Boots on the Ground” Isn’t the Only Way to Deliver Housing Support
Why “boots on the ground” doesn’t always mean better and how remote housing navigation is redefining what access really looks like. The Question We Hear from Every Health Plan It happens in almost every kickoff call. “Do you have boots on the ground in the markets we serve?” It’s a fair question. Housing instability is Read More

CAHP 2025 and the Future of Housing Stability in CalAIM
At this year’s California Association of Health Plans (CAHP) conference, one theme echoed across every panel, hallway, and breakout room: housing is the next frontier of healthcare—but the path forward under CalAIM is still being written. With the six-month rental support period ending for many members and major program changes coming in 2026, health plans Read More

Privately Financed Affordable Housing
Privately financed affordable housing (PFAH) has become one of the most important developments in the housing field over the last six years. It is housing built with private capital, enabled by new zoning and regulatory incentives, and made feasible through cost discipline and creative financing often without the traditional layers of government subsidy. For health Read More

Housing Support for Veterans: A Program Built on Reality, Not Assumptions
Veterans face distinct, predictable housing challenges that require structured support beyond temporary fixes. Upside delivers coordinated housing navigation designed specifically for the complexity veterans bring—combining clinical understanding, behavioral health expertise, and systematic barrier removal. The Reality: Veterans’ Housing Barriers Are Systemic, Not Individual Housing instability among veterans is persistent and multifaceted. While the visible face Read More

Helping Members Starts with Helping Them Get Home
For members navigating housing instability, every day can feel like crisis management — and for the Care Guides working alongside them, it often is. But through each phone call, application, or motel check-in, one truth becomes clear: when a member gets housing, everything else starts to change. Housing isn’t just shelter. It’s health care. It’s Read More

Health Plans Want More AI. But What Do Members Really Need?
Why automation can’t replace empathy in the housing stability journey Artificial intelligence is everywhere—redefining workflows, reducing administrative burdens, and powering efficiencies in healthcare at a staggering pace. For health plans, the promise of AI is particularly compelling: faster intake, better data management, predictive modeling, automated outreach. But when the challenge at hand is housing instability, Read More

Preventing Care Guide Burnout to Support Member Housing Stability
At Upside, we see housing support as a long-term commitment—not just to the members we serve, but to the Care Guides who walk alongside them. For people facing housing instability, a steady, empathetic Care Guide can be the difference between falling through the cracks and finding a clear path forward. But that level of commitment Read More

Beyond Placement: What It Takes to Modernize Legacy Systems for Housing Stability
Few challenges are as dynamic and emotionally charged as housing. For health plans committed to improving outcomes, supporting members through stable housing is no longer just a compliance requirement it’s a moral and operational imperative. Yet the systems we’ve inherited to manage this process often feel like they were built for a different era entirely. Read More