Housing First: Upside's Revolutionary Healthcare Approach
Thu Jan 22 2026
"Housing stability is not binary." In this episode, Keren Etkin welcomes back Jake Rothstein, Founder and CEO of Upside, to discuss how his company is bridging the gap between the housing and healthcare industries.
Jake shares the "story arc" of Upside - from helping his grandmother find a rental to building a national network of 33,000+ vetted apartment communities that serves the most vulnerable Medicare and Medicaid populations.
Key topics discussed:
How housing stability directly impacts clinical ROI (and how payers measure it).
The pivot from a consumer-facing concierge service to a B2B payer-focused model.
The "Secret Sauce": Using AI to handle administrative complexity while keeping human "Care Guides" at the center of advocacy.
Why the system collapses if we don't move "upstream" to solve Social Determinants of Health (SDOH).
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"Housing stability is not binary." In this episode, Keren Etkin welcomes back Jake Rothstein, Founder and CEO of Upside, to discuss how his company is bridging the gap between the housing and healthcare industries. Jake shares the "story arc" of Upside - from helping his grandmother find a rental to building a national network of 33,000+ vetted apartment communities that serves the most vulnerable Medicare and Medicaid populations. Key topics discussed: How housing stability directly impacts clinical ROI (and how payers measure it). The pivot from a consumer-facing concierge service to a B2B payer-focused model. The "Secret Sauce": Using AI to handle administrative complexity while keeping human "Care Guides" at the center of advocacy. Why the system collapses if we don't move "upstream" to solve Social Determinants of Health (SDOH).