Housing Is Healthcare: Jake Rothstein of Upside on ROI, and Aging-in-the-Right-Place

On this Foresight Radio recording of Tech Tuesday, host Steve Moran sits down with Jake Rothstein , founder of Papa and now Upside (formerly UpsideHom), to rethink what "aging in place" really means. Starting from his grandparents' journey, Jake shares how Upside became a " housing easy button " for health plans — matching vulnerable members to safe, affordable apartments and support without laying a single brick. We cover the 5 D's trigger events, why case managers are pivotal, how flex funds unlock moves (deposits, movers, utilities, furniture), and why housing stability delivers a clear ROI for insurers. Jake also gets candid about early failures (hello, Golden Girls co-living) and tells a powerful success story about Joanna, who went from an unsafe unit to long-term stability. If you're a senior living operator , hear how Upside can fill your buildings by transitioning the right residents from SNFs and the community. Plus: Steve teases a big announcement coming later this week… Top Takeaways Aging-in-the-right-place > aging-in-place: Most older adults want to stay home—until a trigger (the 5 D's: Death, Disaster, Divorce, Disability, and Downsizing ) makes it unsafe or unsustainable. Housing as healthcare: Upside partners with Medicare Advantage/Medicaid plans; stable housing cuts risk and cost, creating measurable insurer ROI . The "easy button" for case managers: Health plans refer members with housing instability; Upside rapidly matches them via a national network (multifamily, single-family, rooms, Section 8). Resources many seniors miss: Upside helps unlock SNAP , benefits, and plan flex funds (deposits, movers, utilities, furniture) to make moves possible. What didn't work (and why): Early "Golden Girls" co-living in single-family homes didn't scale—apartment partnerships and tech to track real-time inventory did. Operators benefit: Upside transitions qualified members from SNFs to IL/AL/MC , helping communities increase occupancy—including private-pay options from unlocked assets. Advocacy + access wins: Beyond units, families need navigation ; the right advocate turns a confusing system into sustainable stability.

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Housing Is Healthcare: Jake Rothstein of Upside on ROI, and Aging-in-the-Right-Place is an episode from Foresight Radio by Senior Living Foresight Radio.

This episode is 32:02 long.

This episode was published on Oct 29, 2025.

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