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

1. 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.

2. Housing as healthcare: Upside partners with Medicare Advantage/Medicaid plans; stable housing cuts risk and cost, creating measurable insurer ROI.

3. 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).

4. Resources many seniors miss: Upside helps unlock SNAP, benefits, and plan flex funds (deposits, movers, utilities, furniture) to make moves possible.

5. 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.

6. Operators benefit: Upside transitions qualified members from SNFs to IL/AL/MC, helping communities increase occupancy—including private-pay options from unlocked assets.

7. Advocacy + access wins: Beyond units, families need navigation; the right advocate turns a confusing system into sustainable stability.