Upside Secures $20 Million Series A to Bolster Healthcare-Focused Housing Platform
Upside, a scalable housing stability platform, has successfully closed a significant $20 million Series A funding round. This investment aims to further address the pressing U.S. housing crisis through a unique healthcare lens.
Aquiline Leads Investment Round
The funding round was spearheaded by Aquiline, with contributions from Flare Capital Partners and continued support from existing investors such as 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.
Dante La Ruffa, principal and partner at Aquiline Venture and Growth Strategy, highlighted the importance of addressing housing instability, stating it as “one of the most persistent drivers of avoidable healthcare spending.”
Strategic Opportunities and Expansion Plans
La Ruffa expressed enthusiasm about partnering with Upside, noting the company’s potential to leverage Aquiline’s strategic connections across health insurance, payer, and broker channels. He emphasized the prospects for product adjacencies that could enhance Upside’s value proposition for all stakeholders.
The newly acquired funds will be strategically utilized across Medicaid, Medicare Advantage, and employer-sponsored markets. Upside also plans to enhance its operational capabilities by hiring additional managers.
Innovative Healthcare Solution Founded in 2020
Established in 2020 by Jake Rothstein and Peter Badgley, Upside is recognized as the only nationally scalable housing stability platform tailored specifically for healthcare needs. Currently operating in 10 states, the company collaborates with health plans and employers to preemptively identify and stabilize individuals facing housing instability before it escalates into a medical crisis.
Rothstein, who previously co-founded Papa, emphasizes the platform’s unique care model, which integrates housing navigation, rental and mortgage assistance, senior transition planning, and deposit assistance into workforce benefits packages.
Combining Expertise with Artificial Intelligence
Upside employs licensed social workers and housing specialists, termed “care guides,” alongside an AI-powered “housing organization.” This innovative approach encompasses housing options, case aggregation, and risk flagging. As co-founder and COO Peter Badgley elucidated, AI enhances rather than replaces human interaction, allowing care guides to focus on personal assistance during crises.
Data from the company highlights housing instability as a costly yet solvable gap in the healthcare system, significantly impacting both government and commercial sectors. Health insurers note $9.3 billion in nationwide inpatient costs, while employers observe increased job loss probability among employees who lose their homes.
Proven Impact and Future Investment
Upside’s care model boasts over 90% enrollment rates, stabilizes more than half of its members within 90 days, and delivers up to a fourfold return on investment within 12 months. The platform’s growth trajectory includes collaborations with over 17 state and regional health plans, including four major national payers.
The Series A funding will enhance executive hiring, operational depth, and care leadership capacity. Upside is committed to further investing in its technology platform, which integrates proprietary AI workflows for acuity stratification, housing matching, and case management with a human-centered delivery model.
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