Upside Lands $20M Series A to Solve the U.S. Housing Crisis for Healthcare

Aquiline and Flare Capital Partners co-led the round with participation from existing investors: 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars. The capital scales Upside across Medicaid, Medicare Advantage, and employer benefits.

FORT LAUDERDALE, Fla., June 25, 2026 /PRNewswire/ -- Upside, the only nationally scalable housing stability platform purpose-built for healthcare, today announced a $20 million Series A. Aquiline led the round with Flare Capital Partners and continued support from existing investors including 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars. The capital accelerates Upside's national expansion, builds out go-to-market capabilities across health plans and employers, and deepens investment in the company's AI-supported delivery platform. Upside is led by industry veterans who previously built category-defining healthcare companies, including MDLive, Papa, and Virta Health.

Housing instability is one of healthcare's most expensive and most addressable gaps, and it spans both government and commercial lines of business. Health plans see it in claims: $9.3 billion in inpatient costs nationally, yet most still measure activity over outcomes. Employers see it in workforce data: workers who lose their homes are 11 to 22 percentage points more likely to lose their jobs, and their highest utilizers are frequently the same employees experiencing housing precarity. They are not looking at different problems — they are looking at the same person. And they both need one partner who finishes the work.

Upside was built for that standard. Operating across 10 states, the company pairs dedicated Care Guides with AI-supported housing orchestration, all powered by a proprietary, curated affordable housing inventory database spanning public and non-public data. Together they identify, engage, and stabilize members before housing challenges become medical crises. The model of care delivers 90%+ enrollment, more than half of members stabilized within 90 days, and up to 4x ROI in 12 months, while achieving industry-leading member satisfaction. In just the past 18 months, the platform has expanded rapidly, securing partnerships with more than 17 national, state and regional health plans and is now supporting four of the largest National Payers. "Housing is the highest-cost social problem in healthcare, and most solutions stop at the referral," said Jake Rothstein, Co-Founder and CEO of Upside. "We go beyond that. Upside places people into stable housing and keeps them there. This growth capital means we get to do that for more people, in more markets, more quickly."

Building across plans and employers in parallel

Upside will deploy the Series A funding across Medicaid, Medicare Advantage, and employer-sponsored markets simultaneously. The employer push opens a meaningful new front. Upside's care model translates cleanly into a workforce benefit covering housing navigation, rental and mortgage support, elder transition planning, and deposit assistance. With dedicated go-to-market investment, the company is positioned to bring that benefit to large self-insured employers at scale.

The round also funds leadership hires and operational depth, including Care Guide capacity, partner operations, and care model oversight, so the model that drove these results performs at greater volume without compromise.

"Housing instability is one of the most persistent drivers of avoidable healthcare spend. Upside has the model, team, and infrastructure to address it, and we're excited to partner with the company in its next chapter," said Dante La Ruffa, Partner and Head of Aquiline's Venture & Growth Strategy. "We see significant opportunities to accelerate Upside's momentum through Aquiline's strategic connectivity across health plan, payer, and broker channels, as well as through product adjacencies that further expand the company's value proposition for all key stakeholders."

"The Health Related Social Needs solutions market is approaching the mid-innings of maturity. The first wave saw companies find success with population-wide screening and solutions directories, but stopped short of driving or guaranteeing outcomes. 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," said Dan Gebremedhin, MD, Partner at Flare Capital Partners. "We look forward to partnering with the company to further deploy AI technologies to ensure this valuable service is cost-effective and can be deployed to more populations with proven medical and benefit design ROI."

As part of the investment, Aquiline's Avery Klinger will join Upside's Board of Directors along with Dan Gebremedhin of Flare Capital Partners.

Human-led, AI-accelerated

Upside will continue investing in its technology platform, which combines proprietary AI workflows for acuity stratification, housing matching, and case management with a human-first delivery model. AI handles the repeatable work, surfacing housing options, summarizing cases, flagging risk, so Care Guides stay focused on the complex, relationship-driven work that actually drives outcomes.

"AI does not replace a Care Guide. It frees one up," said Peter Badgley, Co-Founder and COO of Upside. "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."

Since 2020, Upside has stabilized members across every major line of business in healthcare, from D-SNP and Medicaid to commercial and employer-sponsored populations. With this round, the company enters its next phase: larger in reach, deeper in technology, and faster in the markets where housing instability does the most damage. The mission is the same one Upside started with. Resolving housing instability completely, for the people who need it most.

About Upside

Upside is the only nationally scalable housing stability platform purpose-built for healthcare. The company partners with health plans and employers to identify and stabilize members and employees experiencing housing instability, connecting them to safe, supportive housing while reducing avoidable emergency utilization and improving health outcomes. Upside pairs dedicated Care Guides (licensed social workers and housing specialists) with AI-supported housing orchestration to deliver measurable results at scale. The platform serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations across the full housing continuum, from crisis intervention to long-term tenancy support. Founded in 2020 and headquartered in Fort Lauderdale, FL, Upside is redefining how healthcare addresses housing as a foundation of care. Learn more at www.joinupside.com.

About Aquiline

Aquiline is a global private investment firm with offices in New York, London, and Philadelphia that focuses on financial services and technology. As of December 31, 2025, Aquiline had approximately $12 billion of assets under management and deployed approximately $8.3 billion of capital across the firm's strategies since inception.

About Flare Capital Partners

Flare Capital Partners is a leading healthcare technology venture capital firm advancing innovation-driven companies to improve positive health outcomes, broaden care access, and lower healthcare costs. We partner with exceptional founders solving healthcare's hardest challenges, supporting each with our deep sector expertise, unparalleled industry resources, and proven access to commercial opportunities. Our team of established investors and senior operating executives has invested in 80+ companies and has nearly $1 billion in assets under management. Learn more at www.flarecapital.com.

SOURCE Upside