Upside Raises $20M Series A
Upside, based in Fort Lauderdale, Florida, is a housing stability platform designed for the healthcare industry. The company recently announced it has raised $20 million in a Series A funding round to accelerate its national expansion and advance its AI-supported delivery platform.
The round was co-led by Aquiline and Flare Capital Partners. Additional participation included existing investors 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.
Upside plans to use the capital to scale its operations across Medicaid, Medicare Advantage, and employer benefits markets. The funding will also support the expansion of go-to-market capabilities, the recruitment of new leadership, and increased investment in its proprietary AI-supported housing orchestration technology.
Founded in 2020 by Jake Rothstein and Peter Badgley, Upside provides a nationally scalable housing stability platform tailored for healthcare. By pairing human Care Guides with AI-driven workflows, the company identifies, engages, and stabilizes health plan members and employees experiencing housing instability, thereby reducing avoidable medical costs and improving patient outcomes.
Funding Details
Company Website: https://joinupside.com
Company: Upside
Raised: $20M
Round: Series A
Funding Date: June 25, 2026
Lead Investor: Aquiline and Flare Capital Partners
Additional Investors: 645 Ventures, Freestyle Capital, Triple Impact Capital, Techstars
Company Website: https://www.joinupside.com
Software Category: Healthcare Technology