After $20m Funding Round, Upside Seeks To Expand, Evolve ‘housing For Healthcare’ Model

Upside, the company that once aimed to create a platform of “deconstructed senior living” communities, is now focused on “housing for healthcare.”

The company in late June closed on $20 million in Series A funding. Aquiline and Flare Capital Partners led the funding round, which included investments from 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars.

The company previously partnered with apartment complexes to lease units to older adults and bring in certified caregivers to perform services such as non-clinical care management.

Almost four years later, Upside has evolved its model to center on “housing for healthcare,” which is meant to help people including older adults avoid housing instability as their care needs grow. Services include working with Medicaid recipients through care guides that help with coordinating on discovery calls, housing plans, deposits and scheduling move-ins, along with expanding into helping Medicare and Medicare Advantage recipients and employers coordinate for making housing plans for staff. The company’s current targeted partners include health insurers, hospital systems, and self-insured employers.

“If we can do that at scale using what we learned in the direct-to-consumer business, from getting an older adult in the right physical environment, but expanding that to anyone that needed their appropriate physical environment … we could really make a big impact,” Upside Founder and CEO Jake Rothstein told Senior Housing News.

Upside’s leaders are using the funding to hire new staff and up the company’s care guide capacity, partner operations and care model oversight. The company recently brought on a chief technology officer, Brian Lichtlin, who Rothstein attributes to accelerating the pace of technology adoption for Upside.

The announcement comes after 18 months of continuous revenue growth.

Upside’s new funding also will help its leaders open additional lines of business and invest in new technology.

“We’re predominantly in Medicaid, and we’re moving more so into Medicare Advantage and into self-insured employer markets and lines of business,” Rothstein told Senior Housing News. “We’re really excited about those opportunities.”

Upside’s leaders seek to use AI agents as “superhuman care guides” that handle administrative tasks such as helping clients get a driver’s license or apply for an apartment. In doing so Upside is seeking to create “an incredible member experience” while keeping staff involved due to connection being necessary for the role.

According to Rothstein, preventative healthcare measures can only do so much when 20% to 30% of the most vulnerable population are dealing with housing instability.

“That’s the approach that we’ve taken, combining these people using healthcare dollars to pay for housing services,” he said. “It’s a very new thing. Health plans historically know how to do it, and we’ve had to be really prescriptive with them to teach them how to do it and learn it while learning ourselves.”

Upside’s pivot from a disaggregated senior living model to a healthcare housing coordinator began in late 2023. The company soon expanded to operate in 10 states.

For the remainder of 2026, Upside’s leaders will focus on expanding the company’s services and servicing both its health plan customers and employer customers better.

“Enabling them with data is a really important thing, and that’s happening immediately,” Rothstein said.

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