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Jake Rothstein spent nearly six years scaling Papa, a Miami-based company that offers care and companionship to seniors. The business, which pairs elderly Americans with uncertified-yet-vetted pals, helps offer casual services, such as technology support, grocery delivery or even a fun conversation. It has raised upwards of $91 million in venture capital to date.

The company gave Rothstein a deeper look into the priorities of older adults and families as they go through the aging journey. And while Papa was about meeting the elderly where they are, it seems that a few years in, the co-founder began to think of a more complex question: What if “where they are” isn’t as supportive as it should be 24/7?

Rothstein left Papa in January 2020 to launch a more modern take on senior living communities. UpsideHōM is a fully managed, tech-enabled living space for older adults in the United States. After Rothstein and his co-founder Peter Badgley completed a year of beta testing, the duo announced today that they have raised a $2.25 million seed round for UpsideHōM, led by Triple Impact Capital and Freestyle Capital, with participation from Techstars.

Alongside the funding, UpsideHōM announced its next big bet, dubbed a relaunch, that will sit atop its fully furnished apartments that sit throughout Raleigh, Atlanta, Jacksonville, Tampa and South Florida: a software platform to take out all the clutter from move-in and maintenance. The platform will give residents one spot to chat with their house manager, pay bills and access perks such as on-demand tech support, house-keeping and companion visits thanks to a partnership with Papa. The company also offers add-on services and amenities, including freshly prepared meals, grocery delivery, fitness programming and accompanied transportation.

Image Credits: UpsideHōM

Part of UpsideHōM’s focus is in creating personalized solutions. Elders are diverse in age, needs and financial circumstances — which means the turnkey solution needs to be easily adaptable to service needs when they pop up. The company needs to be careful though: It can’t offer traditional caregiver services due to state by state compliance; instead Rothstein describes the offerings as supportive services, not in replacement of health assistant caregivers.

Image Credits: UpsideHoM

When the company first launched, it was betting on a more unconventional idea.

“I thought, let’s solve loneliness even more completely than what Papa is doing by building in companionship,” Rothstein said, instead of letting people order it on demand. The company decided to offer roommate matching services for elders as one of its core services, alongside the aforementioned assisted living characteristics. It didn’t fully stick. Over half of inbound participants responded to the marketing efforts by saying that they liked the idea, but didn’t want to share the space. Today, 50% of UpsideHōM’s business covers individuals or people with spouses or significant others; the other half covers those looking to share units.

The synergies between UpsideHōM and Papa, Rothstein’s previous company, are clear beyond an overlapping customer base. Papa offered up to and almost including actual care, stopping at traditional care-giving services, which require their own vetting and compliance measures. UpsideHōM offers up to and almost including traditional senior living services, but gives supportive services instead of assisted living services, which similarly have their own logistic hurdles to figure out.

As for why Rothstein didn’t just launch supportive living services as a new product vertical within his earlier company, he chalked it up to the “tremendous” opportunity in the former, which warranted it’s own company. He also said that customer acquisition looks different between the two companies.

“At Papa, what we found was that acquiring customers in this space was incredibly challenging [so we went through] the Medicare Advantage route,” he said. “But senior living is a completely different segment.”

The millions in new venture capital money are coming as UpsideHōM prepares for aggressive growth. While the company did not disclose revenue or total residents, it did say it has hit 1,000% in new resident headcount in the first half of 2021 as a vague proxy. As the startup prepares for its next phase of growth, the co-founders will need to focus heavily on sustainable customer acquisition.

Rothstein thinks that downsizing elders into homes that work for them is a simple argument to make.

“You can age in place for as long as it’s practical, but there’s going to be a day and time when it’s not gonna be practical,” Rothstein said. “Why would you want to make this decision after you’ve broken your hip, after you run out of money or after your spouse died?”