Founder Spotlight: Jake Rothstein (Upside)

Welcome to a very special edition of Golden Age of Technology. This week I had the privilege of interviewing Jake Rothstein, co-founder of Upside: a nationwide platform that works with health plans to provide members with housing stability. We discussed Jake’s experiences building Papa and now Upside, from the initial inspiration to the challenges of the building phase. I hope you enjoy learning about the Upside approach to understanding customer needs as much as I did!

— Sarah Richard

P.S. - If you’re an AgeTech founder, investor, or operator based in the NYC area, please consider joining us live at the April AgeTech NYC coffee meetup.

Jake, tell us about Upside.

JR: Upside is the first and only housing stability program for health plans and their members. We promote safe and sustainable housing for long-term member stability - which is critical for overall health and peace of mind. We also work with health plans directly to identify and facilitate affordable housing options to ease financial burdens for members.

If Upside is a magic wand to fix housing instability, what is the specific problem you’re solving?

JR: One of the main issues today is inventory visibility. You have such long waitlists for Section 8 housing that people just are not getting the support they need. For example; there’s a 160K+ waitlist in one of the states we’re working in. That means you might have 15K people ahead of you in line, and there’s just limits to how quickly that line can move, you can’t build 160K additional units overnight. What we provide is a marketplace of curated housing in addition to trained experts in order to match members in need to our 33K apartment communities (and counting!) based on availability and members’ needs. What we have noticed, though, is that people often feel overwhelmed and alone in this journey, and we act as an advocate to help people navigate the challenges of housing instability.

What was your journey to starting Upside?

JR: First, we started Papa after looking for Miami homecare and being laughed out the door of 5 homecare providers. Papa began as a DTC companionship and assistance provider and then in 2019 an update to Medicare Advantage supplemental benefits changed everything for Papa and enabled a payer funded model. As all this was happening and Papa was growing, my grandmother Margarita had to move my grandfather into assisted living and had to pay  $11K/mo for his care there, which wasn’t in her retirement budget. There’s a reason why only about 10% of older adults end up in assisted living, it’s really out of reach for a lot of people. My family stepped in to help sell her house and move her to a more affordable rental apartment near her doctors, friends, and grandkids. And that’s really what started me on the path to building Upside.

After starting Upside as a DTC business to gather critical data on housing as a key social driver of health, we quickly learned that providing appropriate housing for vulnerable populations can improve health outcomes just as much or more than medical intervention.

What did the initial stages of building Upside look like - were you knocking on doors?

JR: I almost hate to use the term hustle, but it really is about hustle. We were knocking on doors, we were walking into apartment leasing offices, we were posting Craigslist and Facebook ads. In the initial stages we were obsessed with the problem not the product, we were really listening to the customer. We’d put an offering in front of a prospect a hundred times as a stake in the ground, and use their feedback to make the offering better. There’s a lot of grittiness involved in starting a business. 

What did the initial conversations about sales look like internally?

JR: Initially we were DTC because we recognized that we needed data before we could approach health plans. We needed to be prepared with data on ROI, asking the plans what data they needed and being conscious of the incentives and motivations of the organizations we’re talking to. Whether it’s a multifamily apartment operator or a family member, we consider who carries the risk and who feels the reward in a given purchasing decision. 

We started off with defining our 3 potential customer models, one where the older adult is the decision maker; one where the caregiver is the decision maker; and one where it’s a hybrid and the older adult and their caregiver partner on the decision. We had to build an entire sales motion around all 3, testing a website, talk track, and sales pitch for each of the 3 sales models.

Distribution is by far the hardest element of this market, because you have a discerning customer who’s been around the block and has really strong preferences. We connect with people through health plans, via case management or other outbound programming. It’s about focusing on what product offering is the stake in the ground that can help your customer do their job better, and at Upside, that’s enabling health plan members to have greater housing stability and therefore better health outcomes.

What are you particularly excited about upcoming for Upside?

JR: I’m excited that we’re finally seeing housing talked about as a solution to impacting healthcare outcomes. Before, the conversation was all about how housing is a problem but now the conversation is shifting to treat housing as a solution. Fundamentally, we don’t want people to struggle with the health impacts of unstable housing. We’re talking about acute or temporary, homelessness and chronic homelessness, but not just in the stereotypical way - when you have an 87 year old on a fixed income whose rent increases, you risk an older adult sleeping in their car, as an example. That’s a terrible but not uncommon situation, and nobody is talking about it enough. 

Upside has worked for years in the industry to change the narrative, and it’s exciting to now be on the forefront of that change. We’re working with health plans to proactively identify, stratify, and intervene in situations of unstable housing. We’re doing the work of building a marketplace to correct the housing inventory mismatch for people on the margin - older adults, but also folks of all ages on Medicaid. We have younger families in the perinatal period we’re supporting to prevent housing instability and a whole host of other vulnerable populations we work with. 

The Upside of Aging

Jake’s journey building Upside highlights the importance of empathy when creating products and services that cater to older adults. The Upside story is a powerful reminder of the need for human-centric approaches to product development when serving vulnerable populations. I’m thankful to Jake and Upside for their contribution to the discussion around housing stability!

The Upside story makes me very hopeful that we can build toward a future in which we truly care for our most vulnerable populations. With folks like Jake and the Upside team leading the charge, I’m certain we’ll get there.

Stay tuned for more stories and insights in the next edition!

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