Jake Rothstein had no intention of rethinking healthcare when he helped his grandmother move out of the family home after his grandfather entered senior living. At that point, he was focused on trying to solve a housing problem.
Yet that experience eventually became the foundation for Fort Lauderdale-based Upside, a startup built on the idea that where someone lives can have just as much impact on their health as the care they receive. Now, investors are betting that idea is ready to scale.
Today, Upside announced that it has raised a $20 million Series A co-led by Aquiline and Flare Capital Partners, with participation from existing investors including 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars. The funding will help the company expand nationally across Medicaid, Medicare Advantage, employer-sponsored healthcare, and commercial health plans.
“We were a totally different business back when we launched,” Rothstein told Refresh Miami in an interview last month.
Upside initially focused on helping older adults and their families find housing directly. But Rothstein and co-founder Peter Badgley soon realized healthcare organizations had a major financial incentive to solve the same problem. Housing instability often leads to higher emergency room utilization, longer hospital stays, and worse health outcomes, making it one of the costliest challenges facing insurers.
That shift paid off when one of the nation’s largest health insurers agreed to pilot Upside’s model in Virginia.
“We started getting referrals very quickly,” Rothstein said. “Within three months, we were housing people at a rate that these health plans had never seen before.”
The pilot eventually expanded into a relationship spanning 22 states. According to Rothstein, the company grew roughly 2,000% during 2025, increasing its team from nine employees to 65. Upside reports it has now secured partnerships with more than 17 national, state and regional health plans. And just a month ago, Rothstein told Refresh Miami that fundraising discussions were underway. Those conversations have now resulted in the company’s first institutional funding round since 2022.
Rather than simply referring patients to community resources, Upside combines licensed social workers and housing specialists, known as Care Guides, with an AI-powered platform that helps identify affordable housing, prioritize cases, and streamline administrative work.
“If you don’t know where you’re sleeping tomorrow night, you don’t care about going to see your primary care doctor,” noted Rothstein.
The company plans to use part of the new funding to continue investing in that technology, though executives say AI is intended to support, not replace, human relationships.
“AI does not replace a Care Guide. It frees one up,” said COO Badgley. “When the repeatable work runs in the background, our team can do more of what only people can do, which is sit with someone in crisis and get them somewhere safe.”
Investors believe that approach reflects where healthcare is heading.
“The Health Related Social Needs solutions market is approaching the mid-innings of maturity,” commented Dan Gebremedhin, MD, Partner at Flare Capital Partners. “What drew us to Upside was the rapid cycle time of referral to engagement to success in closing key needs gaps, starting with housing, in a matter of months.”
Pictured above: Left to right, Upside Co-founders Jake Rothstein, CEO, and Peter Badgley, COO.
READ MORE IN REFRESH MIAMI:
- Housing became a healthcare problem, so Upside built a business around it
- How Papa is turning companion care into a healthcare must-have
- Neurolief raises $6M to fuel U.S. rollout of at-home depression therapy
- Delorean AI wants to give doctors something they’ve never had: A glimpse into the future
