• Andrea Ippolito of SimpliFed: Lactation Support at Population Scale.

• Otto Sipe of Photon Pharmacy: Building Prescription Routing in the face of a 95% market share incumbent.
  

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.

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The arc of success digital health startups is a thoughtfully crafted wedge grows to become your moat, which then defines your right to exist and ability to have human impact at population scale.

Otto Sipe built Photon Pharmacy into a national scale infrastructure for moving prescriptions and patients from clinicians to pharmacies. He and his team did so in the face of SureScripts owning 95% of the prescription routing volume in the US.

In this interview, he walks us through how they designed their wedge, how the think about traction and defensibility in the face of GenAI and Vibe Coding, and what it means to solve hard problems in digital health.

Clip 1: Why Hundreds of Thousands of Faxes per day Was the Right Architecture Choice.

Clip 2 What Does it Mean When Claude Code Can Build Your Interface in 5 Minutes?

Clip 3: Moats are something you worry about on the way down.

In the full episode:

• Why GLP-1 insurance edge cases turned out to be the training ground for selling into health systems

• The price-transparency bet Otto admits Photon got wrong, and why the fix is commercial, not technical

• How retail pharmacies went from blocking Photon to integrating with it directly

• “Tips and tricks from the monopolies that came before us” on scaling a fax operation

• The agentic prescribing future: what collapses when an AI can navigate benefits faster than any human party

• Otto’s advice for founders staring down a dominant incumbent in a regulated market

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The arc of success digital health startups is a thoughtfully crafted wedge grows to become your moat, which then defines your right to exist and ability to have human impact at population scale.

Andrea Ippolito has built Simplifed into a national scale telehealth platform delivering lactation and post-partem support in all 50 states. She has contracts with all of the major payers and just raised a $10M series A. When she started Simplifed 6 years ago, the ACA Lactation mandate was almost a decade old, but fewer than 15 percent of lactation consultants billed insurance and less than 5% of those claims got paid. In this interview she shares the steps that she took to get here.

Clip #1 Building for Understaffed Healthcare Mandates.

One reason that I asked Andrea to be my first guest on Right to Exist is that lactation support is structurally similar to many other spaces, pediatric asthma, osteoporosis, menopause, hormone replacement therapy, and others.

What does it take to build for a population or condition that is understaffed or under-resourced by conventional enterprise healthcare?

Clip #2: Integration Friction vs. Product Perfection

One of the common questions that founders have at pre-seed and seed is how much to invest in integration rails with existing healthcare infrastructure.

In Andrea’s case, the signal from OBGYNs was that smooth integration with care flows, and more importantly, feedback loops about how referrals had been handled, would be the driver for adoption.

Clip #3 When Lactation Support Drives more than Lactation Outcomes

Part of the secret sauce for Andrea, was the realization that Simplifed’s contact area with patients was much broader than that of the intermittent visits to OBGYNs who drove the initial referrals.

This meant that they were able to catch things like post-partem depression, preeclampsia, and gestational diabetes and route the patients in need of additional care back to the clinic.

Subscribe below to watch the entire 30 minute conversation.

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