/Companies

UpsideHoM

Techstars '20

Fort Lauderdale, US · Founded 2020 · Delaware corporation · 54 employees on LinkedIn · 5 known investors

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Upside provides end-to-end housing stabilization services for individuals experiencing housing instability within healthcare settings, serving health plans, employers, and their members across Medicaid, Medicare, and employer coverage. The company coordinates case management, local navigation, and community partnerships to resolve complex housing situations and improve health outcomes.

Also known as Upside · UpsideHom · UpsideHōM

Founders & leadership

UpsideHoM was founded in 2020 by Jake, Peter Badgley, and Jacob Rothstein.

JJake
JakeCEOJake is the founder and CEO of Upside, which provides housing stabilization services and case management to health plans and their members. He has over a decade of experience founding and scaling organizations.
PBPeter Badgley
Peter BadgleyCo-FounderPeter Badgley is Chief Operating Officer at Upside, a housing stability services company that serves health plans and their members.
JR
Jacob RothsteinCo-founder

Board

AHAaron Holiday
Aaron HolidayBoard directorCo-Founder, Managing Partner at 645 Ventures

Investors · 5

Reported raises · per SEC filings

Form D private placements

$8.7M disclosed across 3 of 4 rounds · 2021–2025

▶$425KraisedJan 2026 · 5 investors · Residential
Rule 506(b)
Officers, directors & promoters on the filing
  • Jacob S RothsteinExecutive Officer, Director
  • Aaron HolidayDirector
  • Peter D BadgleyExecutive Officer, Director
Offering amount
$500K
Amount sold
$425K
Minimum investment
$25K
First sale
Dec 2025
Incorporated
Corporation, Delaware
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$500KraisedOct 2024 · 2 investors · Residential
Rule 506(b)
Officers, directors & promoters on the filing
  • Peter BadgleyExecutive Officer, Director
  • Aaron HolidayDirector
  • Jacob RothsteinExecutive Officer, Director
Offering amount
$2M
Amount sold
$500K
Minimum investment
$250K
First sale
Oct 2024
Incorporated
Corporation, Delaware, 2020
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$7.8MraisedApr 2022 · 17 investors · Residential
Rule 506(b)
Officers, directors & promoters on the filing
  • Jacob S RothsteinExecutive Officer, Director
  • Peter D BadgleyExecutive Officer, Director
Offering amount
$7.8M
Amount sold
$7.8M
Minimum investment
$5K
First sale
Apr 2022
Incorporated
Corporation, Delaware, 2020
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$2MofferedMar 2021 · Other Technology
Rule 506(b)
Officers, directors & promoters on the filing
  • Peter D BadgleyDirector
  • Jacob S RothsteinDirector
Offering amount
$2M
Minimum investment
$50K
Incorporated
Corporation, Delaware, 2017
Federal exemptions
06b
Full filing on SEC EDGAR ↗

Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.

Company profile

researched Sep 2026

Upside, founded in 2020 as UpsideHom, is a Fort Lauderdale, Florida company that works on housing for older and vulnerable adults. Its original model was described as "deconstructed senior living": rather than building or converting a dedicated facility, the company leased or purchased studio to three-bedroom units in existing amenity-rich condo and apartment buildings and subleased them to older renters, either alone, with friends, or with roommates matched through proprietary matching software. Base rents bundled furnished common areas, housekeeping, cable, electricity and maintenance, along with twice-weekly Papa Pals companionship visits, with optional add-on services. Residents were typically aged 60 to 85, and the company screened and interviewed applicants by video or in person before placement.

In September 2022 the company, then operating as Upside, launched Upside+, extending its offering with certified caregivers providing non-clinical care management in members' apartments, referrals to physicians and specialists, meals and transportation, delivered in partnership with home care agency TheKey. Rates were all-inclusive and typically around $6,000 per month, with members able to add, decline or pause individual services.

Upside currently presents itself as a housing-stability platform for health plans, health systems and employers. Members are identified by referral or by system flags indicating risk, then assigned a "Care Guide" who builds a housing plan covering where the member could live, assistance with deposits and move-in costs, and the steps required, and who stays engaged until the housing situation is resolved. The company states coverage across all 50 states on a 24/7 basis, a network of more than 750,000 properties, and multilingual care guides, and it publishes free plain-language housing guides on eviction, deposits and moving, affordable housing, senior downsizing and local resources.

Founding story

Jake Rothstein traced the idea to his own family: after his grandfather died, his 87-year-old grandmother was living alone in a large four-bedroom house with stairs that had become difficult after knee-replacement surgery. The family sold the house and moved her to an apartment in the same neighborhood, near her doctors and grandchildren, and Rothstein found himself driving her at night and logging into her bank each month to manage a scattering of utility and rent bills. He concluded that many older adults do not need hands-on personal care but do need bundled supportive services, a single trusted point of contact and one monthly bill, and framed the goal as aging in "the right place" rather than aging in place. He also observed that his grandmother and her friends, many widowed or divorced, disliked living alone but wanted to retain independence. UpsideHom was his fifth company; he previously co-founded Papa with his cousin Andrew Parker.

Business model

Upside began as an operator of furnished, service-bundled apartments for older adults: it bought or leased units in existing amenity-rich condo and apartment buildings and subleased them to individual renters, either as private studios/one-bedrooms or as shared two- to three-bedroom apartments with matched roommates. The base monthly price bundled furnished common areas, housekeeping, cable, electricity, maintenance and twice-weekly Papa Pals visits, with optional paid add-ons such as meal delivery, transportation, entertainment and concierge services. In 2022 it layered on Upside+, an all-inclusive service tier including caregiving. The current model is business-to-business: health plans, health systems and employers contract for housing-stabilization services delivered to their members at no cost to the member.

Initially rental revenue from subleasing units to residents, supplemented by referral-style fees paid by discounted vendors, with rooms starting at about $1,500 per month and optional services billed as add-ons. The Upside+ tier used all-inclusive monthly rates of roughly $6,000 that varied with the services selected. Third-party research classifies the company's revenue as recurring.

Traction

In 2020 the company reported growth of roughly 20% week over week, homes across Florida, residents aged 60 to 85 with more than 30% male, and less than $1 million raised. By September 2022 it operated in 78 markets across 22 states, and said nearly a third of members had requested a care option like Upside+. Third-party research lists 17 employees as of February 2024.

Latest developments

Upside has shifted its public positioning to housing stabilization for healthcare organizations, describing a Care Guide-led intake, planning and navigation process delivered at no cost to covered members, coverage in all 50 states around the clock, and a network of more than 750,000 properties.

▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies

Market position

The company positions itself between traditional senior living and independent housing, describing its original model as "deconstructed senior living" for the roughly 90% of older adults who say they want to age outside an institutional setting, and targeting people who have considered independent or assisted living and rejected it. Management said it had no near-term plans to enter traditional senior living. Comparable companies identified in third-party research include Hyatus Stays, Better Coliving, Nursesbnb and Social Spaces.

Rather than developing purpose-built senior housing, the company placed older adults into units within existing multi-generational apartment and condo buildings, which it said allowed a wider range of price points and faster geographic expansion, and offered co-living arrangements that reduced cost while addressing isolation. Proprietary roommate-matching software combined with human screening interviews supported placements, and the company was building its own property management system during the Techstars program. In its current healthcare-facing form, the company emphasizes solve-to-completion navigation by a named Care Guide rather than a referral hand-off or list of resources, a human-led process supported by AI, and round-the-clock nationwide coverage.

Technology

The company developed proprietary roommate-matching software used to screen applicants and pair them by interests and living styles, and during the Techstars program was building an internal property management system. Its current platform combines smart intake — accepting referrals and flagging members heading toward a housing crisis — with human Care Guides, described as a human-first approach strengthened by AI.

Go-to-market

In its co-living phase the company reached residents primarily through inbound phone inquiries, and used content generation, press and media outreach, and engagement with industry thought leaders, large organizations, government bodies, health systems and payers to educate the market about an unfamiliar model. It also connected residents to the community through partnerships with Jewish Community Centers and local YMCAs. Its current go-to-market is partnership-led, inviting health plans, health systems and employers to contract for member housing stabilization, while offering free public housing guides and a direct intake path for individuals.

Originally older adults, typically aged 60 to 85, who wanted to live independently rather than in an institutional setting, including those seeking roommates or shared apartments. Today the company markets to health plans, health systems and employers, serving their members across Medicaid, Medicare and employer-sponsored coverage, and also provides free guidance to individuals facing eviction, move-in cost barriers, affordable housing searches or senior downsizing.

Geography

Headquartered in Fort Lauderdale, Florida. The company launched in the South Florida region in 2020 with locations across Florida, including Boca Raton, and planned entries in Raleigh and Atlanta. By September 2022 it operated in 78 markets across 22 states, with a stated goal of adding 100 new U.S. markets. Its current site states coverage in all 50 states, 24/7/365.

History

Jake Rothstein and Peter Badgley launched UpsideHom in February 2020 in Fort Lauderdale, Florida, initially offering turnkey co-living apartments for older adults in Florida with expansion planned to Raleigh and Atlanta. The company joined the first cohort of the Techstars Future of Longevity Accelerator, a 13-week remote program run with Pivotal Ventures, which ended with a demo day on December 8, 2020. By September 2022 the company, by then operating as Upside, was active in 78 markets across 22 states and targeting 100 new U.S. markets, and it launched the Upside+ service tier with home care partner TheKey. The business subsequently repositioned toward healthcare payers and employers, marketing nationwide housing-stability navigation rather than senior co-living units.

Risks & controversies

The founders described market education and trust-building as the central challenges: the concept was unfamiliar to partners, vendors and prospects, and moving is a high-stakes, often one-time decision for less mobile or financially constrained older adults. The company initially required 12-month commitments, partly due to Covid-19, limiting flexibility for residents.

Compiled by commissioned research from 6 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
EmployeesFeb 202417 employees
HeadcountAug 202654
Markets servedSep 202278 markets
Properties in networkJan 2026750,000 properties
Resident age rangeJan 202060-85
Share of members requesting a care option like Upside+Sep 2022nearly one third
Share of residents who are menJan 2020more than 30%
Starting price per roomJan 2020$1.5K
States coveredJan 202650 states
States servedSep 202222 states
Total funding raised to date (company statement)Jan 2020less than $1 million
Typical all-inclusive monthly rate for Upside+Sep 2022$6K
Weekly growth rateJan 202020% week over week

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

Related companies · 5

AARPAARP Services is the commercial arm of AARP that connects companies with the 50+ population through brand licensing, marketing, audience data, and innovation services. It helps organizations develop and market products and services tailored to aging consumers while leveraging AARP's trusted brand and member insights.
ZillowZillow operates an online real estate marketplace where consumers can search homes for sale and rentals across US and Canadian cities, view mortgage rate information, and access home financing through Zillow Home Loans. It covers residential property listings, apartments and houses for rent, and mortgage services nationwide.
A Place for MomA Place for Mom is a senior care referral service that helps families find and compare senior living and care options, including assisted living, memory care, independent living, home care, nursing homes, and senior apartments. It also provides guides and resources such as VA benefits information for long-term care.
UpsideUpside operates a cash-back marketplace for brick-and-mortar commerce, connecting consumers with retailers such as gas stations, grocery stores, restaurants, and hardware stores. Retailers gain additional profit while consumers earn increased purchasing power on everyday purchases.
Care.comCare.com operates a marketplace that connects families with professional caregivers for childcare, senior care, pet care, and household services. The company also provides employer-sponsored family care benefits and payroll solutions for caregivers and agencies.

Companies working in the same space as UpsideHoM.

Timeline · 4

launches, deals, and filings
Sep 2022
Partnership with home care agency TheKey

Upside partnered with TheKey (formerly Home Care Assistance) to deliver the caregiving component of Upside+.

source ↗

Sep 2022
Launch of Upside+ home-based services

Upside launched Upside+, adding certified caregivers for non-clinical care management in members' units, plus referrals to physicians and specialists, meals, transportation and Papa Pals access. All-inclusive rates were described as usually around $6,000, with services able to be added, dropped or paused.

source ↗

Jan 2022
Rebrand from UpsideHom to Upside

The company, previously known as UpsideHom, began operating under the name Upside.

source ↗

Jan 2020
Selected for Techstars Future of Longevity Accelerator

UpsideHom joined the inaugural Techstars Future of Longevity Accelerator, a 13-week remote program run with Melinda Gates' Pivotal Ventures, alongside nine other companies; demo day was held December 8, 2020.

source ↗

Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.

Legal entities · 1

corporate structure
UpsideHoMDelaware

▸Research sources · 6

primary sources listed

6 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does UpsideHoM do?
Fort Lauderdale company providing housing stabilization and navigation services for health plans, health systems and employers.
Who founded UpsideHoM?
UpsideHoM was founded by Jake, Peter Badgley, Jacob Rothstein in 2020.
Who are UpsideHoM's investors?
UpsideHoM's investors include 645 Ventures, Equitage Ventures, L.L.C., Flare Capital Partners, Techstars, Freestyle Capital.
How much funding has UpsideHoM raised?
UpsideHoM has disclosed $8.7M raised across 3 of its 4 known rounds.
Where is UpsideHoM headquartered?
UpsideHoM is headquartered in Fort Lauderdale, US.