21 min

Episode 5:5 Jake Rothstein with UpsideHōM on Shaping the Future of Senior Living Glowing Older

    • Business

UpsideHōM combines the best of senior living communities with aging in place, by recreating the experiential piece of senior living in a less stigmatized, more flexible, affordable way. Learn how this deconstructed, intergenerational model supports older adults with a wide range of services including internet, housekeeping, transportation, food delivery, wellness, and lifelong learning—customized for every stage of aging.

About Jake

Jake Rothstein is the CEO and Founder of UpsideHōM, whose mission is to enhance the quality of life for older adults everywhere. UpsideHōM is the first and only fully managed, shared living option for older adults, providing a turnkey, affordable and appealing alternative to traditional senior living.

Jake previously co-founded Papa - a company which pairs older adults and families with “Papa Pals” for companionship and assistance with everyday tasks - based on experience with his own grandfather (who he called Papa). Witnessing the wide-spread nature of loneliness, isolation and unaffordable housing options for older adults, Jake developed the idea for UpsideHōM, which would provide a solution to more completely tackle these challenges at scale.

With a background in technology sales, operations and management, Jake has experience building and running successful, international teams, selling enterprise software into the Global 2000.

Jake holds a BA in Economics from the University of Florida. He is a FAA certificated Private Pilot who enjoys flying, outdoor running and spending time with his incredible wife Sharona and their Goldendoodle Louie.

Key Takeaways


Technology is a key component of the UpsideHōM business model, enabling efficiencies and cost savings for residents by leveraging the gig economy.
Food and transportation are older adults’ primary requests for services. UpsideHōM partners with Papa and local pre-prepared meal delivery services.
UpsideHōM provides baseline services like wi-fi and housekeeping; the rest of the services are provided “a la carte” so residents are not paying for what they don’t need.
Going forward, the company will leverage aggregate data and AI to support resident wellbeing and encourage positive health outcomes.

UpsideHōM combines the best of senior living communities with aging in place, by recreating the experiential piece of senior living in a less stigmatized, more flexible, affordable way. Learn how this deconstructed, intergenerational model supports older adults with a wide range of services including internet, housekeeping, transportation, food delivery, wellness, and lifelong learning—customized for every stage of aging.

About Jake

Jake Rothstein is the CEO and Founder of UpsideHōM, whose mission is to enhance the quality of life for older adults everywhere. UpsideHōM is the first and only fully managed, shared living option for older adults, providing a turnkey, affordable and appealing alternative to traditional senior living.

Jake previously co-founded Papa - a company which pairs older adults and families with “Papa Pals” for companionship and assistance with everyday tasks - based on experience with his own grandfather (who he called Papa). Witnessing the wide-spread nature of loneliness, isolation and unaffordable housing options for older adults, Jake developed the idea for UpsideHōM, which would provide a solution to more completely tackle these challenges at scale.

With a background in technology sales, operations and management, Jake has experience building and running successful, international teams, selling enterprise software into the Global 2000.

Jake holds a BA in Economics from the University of Florida. He is a FAA certificated Private Pilot who enjoys flying, outdoor running and spending time with his incredible wife Sharona and their Goldendoodle Louie.

Key Takeaways


Technology is a key component of the UpsideHōM business model, enabling efficiencies and cost savings for residents by leveraging the gig economy.
Food and transportation are older adults’ primary requests for services. UpsideHōM partners with Papa and local pre-prepared meal delivery services.
UpsideHōM provides baseline services like wi-fi and housekeeping; the rest of the services are provided “a la carte” so residents are not paying for what they don’t need.
Going forward, the company will leverage aggregate data and AI to support resident wellbeing and encourage positive health outcomes.

21 min

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