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.<\/p>\n
\u201cWe were a totally different business back when we launched,\u201d Rothstein told Refresh Miami <\/a>in an interview last month.<\/p>\n 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.<\/p>\n That shift paid off when one of the nation\u2019s largest health insurers agreed to pilot Upside\u2019s model in Virginia.<\/p>\n \u201cWe started getting referrals very quickly,\u201d Rothstein said. \u201cWithin three months, we were housing people at a rate that these health plans had never seen before.\u201d<\/p>\n 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. Just a month ago, he told Refresh Miami that fundraising discussions were underway. Those conversations have now resulted in the company\u2019s first institutional funding round since 2022.<\/p>\n \u2713<\/p>\n Check your inbox for a confirmation email.<\/p>\n 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.<\/p>\n \u201cIf you don\u2019t know where you\u2019re sleeping tomorrow night, you don\u2019t care about going to see your primary care doctor,\u201d noted Rothstein.<\/p>\n 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.<\/p>\n \u201cAI does not replace a Care Guide. It frees one up,\u201d said COO Badgley. \u201cWhen 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.\u201d\u00a0<\/p>\n Investors believe that approach reflects where healthcare is heading.<\/p>\n \u201cThe Health Related Social Needs solutions market is approaching the mid-innings of maturity,\u201d commented Dan Gebremedhin, MD, Partner at Flare Capital Partners. \u201cWhat 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.\u201d<\/p>\n Pictured above: Left to right, Upside Co-founders Jake Rothstein, CEO, and Peter Badgley, COO.<\/p>\n READ MORE IN REFRESH MIAMI:<\/p>\n I am a Miami-based technology researcher and writer with a passion for sharing stories about the South Florida tech ecosystem. I particularly enjoy learning about GovTech startups, cutting-edge applications of artificial intelligence, and innovators that leverage technology to transform society for the better. Always open for pitches via Twitter @rileywk or www.RileyKaminer.com.<\/p>\n ![\"Riley](\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2025\/10\/4q0a7418-1.jpeg\")
<\/a> <\/p>\n<\/a>Latest posts by Riley Kaminer (see all<\/a>) \t<\/p>\n","protected":false},"excerpt":{"rendered":"Jake Rothstein had no intention of rethinking healthcare when he helped his grandmother move out of the family…\n","protected":false},"author":2,"featured_media":319655,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[15],"tags":[225,227,226],"class_list":["post-319654","post","type-post","status-publish","format-standard","has-post-thumbnail","category-hialeah","tag-hialeah","tag-hialeah-headlines","tag-hialeah-news"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/319654","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/comments?post=319654"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/319654\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/319655"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=319654"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=319654"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=319654"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}