Right to Exist is the Healing Healthtech interview series that follows founders’ paths as they manifested their projects’ right to exist as a novel offering to enterprise-scale healthcare. Previous episodes included.
Every founder in this series has had to convince enterprise healthcare to pay for something it wasn’t built to buy. Jake Rothstein has done it twice. At Papa, he turned companionship for older adults into a Medicare Advantage benefit and rode a 2019 rule change from zero to a hundred million dollars of ARR in several years. At Upside, he is doing it with housing, a messier social need than food or transportation. The product isn’t immediately apparent as medical: it’s an apartment, a lease, a care guide, and a landlord.
Last month Upside closed a $20 million Series A led by Aqualine, with Flare Capital participating. It works across ten states with more than seventeen regional health plans and four of the largest national payers.
Healthcare has named housing the top social determinant for fifteen years and funded little of it. This conversation gets into the payment, measurement, and design choices Upside used to change that. Four moments are open below; the full interview is under the paywall.
The attribution problem when working with SDoH
Ask a plan why it won't fund a social intervention and you'll hear that outcomes can't be attributed to any one vendor. Jake reads attribution differently: it is the reason plans give when a problem is too small to be worth solving. He reframed housing as the biggest unturned stone in social determinants, on the logic that a member without stable housing can't reliably eat well, get to appointments, or take delivery of medication. With that framing, attribution came up less.
Getting paid for outcomes, not activity
The social-needs category is full of companies reporting referrals made and resources connected. Those are activity metrics, and Upside was built to be paid on something else: enrollment, stabilization inside ninety days, and measurable movement toward stable housing. Jake draws a working line between a leading indicator a payer will underwrite and an activity it will discount.
"I can't house that person"
Hand Upside a member with no income living under a bridge and the honest answer is that they can't house that person yet. Housing is a continuum, not a binary of housed and unhoused. Getting someone from the street into a shelter is a measurable step with its own ROI, as is the move from a shelter to a group home. Upside builds its contracts around the rungs of that ladder rather than a single end state.
The advice for founders who are early.
His counsel to anyone selling the not-yet-reimbursable: stay lean, keep the business alive, and be there when the problem grows too big for the buyer to ignore. And some luck.
Why this matters if you’re building
If you’re selling something healthcare wasn’t set up to buy, four decisions in this interview are worth borrowing.
Speak the buyer’s language, from the buyer’s seat. Upside hired its own actuaries out of the health plans, former Optum and UHC people, and built its ROI model to the standard a plan’s actuary would apply. It then stripped HEDIS and star ratings out of that model, because plans discount the soft metrics and weigh medical cost savings, ED reduction, and length of stay. Offering to be judged on the hard numbers reads as credible to the person on the other side of the table.
Find the dollars before you find the demand. The channel wasn’t a better pitch. It was getting written into states’ Medicaid managed-care RFPs as a scalable housing-stability benefit, then taking the full contract when the plan won the bid. The money for a new benefit often already exists, mislabeled and underused; the work is locating the flexible dollar rather than inventing a budget line.
Pick your wheelhouse and hand off the edges. Housing touches employment, credit, documentation, and behavioral health in a way food and transportation don’t. Upside got repeatable at the housing-specific components, became the coordination layer around them, and routed everything else back to plan case managers and community organizations. That focus is part of why they hold an engagement rate most Medicaid programs don’t.
Pressure-test the moat you’ll have in three years, not today. Jake will tell you technology is commoditizing. What compounds is the matchmaking data: which member profile fits which unit, fastest, learned over thousands of placements, sitting on a two-sided marketplace where volume in a market earns better landlord relationships.
None of these were timing alone. They were design choices that made a non-medical product legible to a medical buyer, one decision at a time.
🔒 The full conversation is below for subscribers.
We get into the hypotheses Upside got wrong, why they were afraid of Medicaid and got pulled in anyway, how they shut down a working direct-to-consumer business in 2023 to focus on payers, and how they hold an eighty-five to ninety percent engagement rate in a Medicaid population.
