Meet The Disruptors: Jake Rothstein Of UpsideHōM On The Five Things You Need To Shake Up Your Industry

An Interview With Fotis Georgiadis

Don’t manage the way you want to be managed; learn what makes your team members tick, what motivates them, and what challenges them.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jake Rothstein, CEO and Co-Founder of UpsideHōM.

Jake Rothstein serves as CEO 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 turn-key, affordable and appealing alternative to traditional senior living. Jake also previously co-founded Papa based on experiences with his own grandfather (who he called Papa).

With a background in technology sales, operations and management, Jake has experience building and running successful, international teams.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Before starting UpsideHōM, I co-founded Papa — a company that pairs older adults and families with “Papa Pals” for companionship and assistance with everyday tasks. I launched Papa with my cousin after I faced these challenges with my own grandfather. Witnessing the wide-spread nature of loneliness, isolation and unaffordable housing options for older adults, I was inspired to conceptualize the idea for Papa — and eventually UpsideHōM with co-founder Peter Badgley.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Our business model itself is disruptive as we’re utilizing existing non-senior living real estate to create alternative options for independent older adults. By doing this, we have been able to create intergenerational communities and connections, which we’ve seen support longevity and wellness.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When starting UpsideHōM, we initially thought that we should focus on single-family homes. It was a big challenge because consistency in quality was hard to come by in the single-family home market. We learned that you can’t make assumptions about what people may want; you need to put yourself out there in the market and learn then iterate based on those learnings.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

One of my former bosses, a sales leader, has made a tremendous impact on my career. He really helped me learn how to scale teams, build organizations, and manage people. Most importantly, he taught me that you cannot manage people the way you want to be managed. You need to manage them the way they need to be managed and come to understand their motivations and work style to manage them effectively.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Unfortunately, disruption means displacement in many cases. Displacement can be a negative for some people, but with any disruption there are winners and losers. As it pertains to UpsideHōM, we don’t see ourselves as disrupting the market but more so additive. We’re creating a new segment rather than disrupting the existing one. We’re disrupting the space while growing the market rather than trying to forcefully carve out a space for ourselves. The best businesses are the ones that bake a new pie rather than steal someone else’s piece.

Can you share five of the best words of advice you’ve gotten along your journey?

  • Persistence is key when you’re trying to build something new. Those who persist are going to be able to face the obstacles that inevitably pop up along the way.
  • Treat everyone like they’re your own parents or grandparents and lead with empathy. Good things will come when you treat your customers well.
  • The road to success is not a straight line. You have to paint a number of paths to success; don’t ever limit yourself to just one.
  • Don’t make assumptions without putting into practice first.
  • Don’t manage the way you want to be managed; learn what makes your team members tick, what motivates them, and what challenges them.

We are sure you aren’t done. How are you going to shake things up next?

Eventually, we want to take UpsideHōM internationally as we’re seeing this demographic face the same challenges around the world. Before doing so, we’re tackling the U.S. and plan to expand into 100 new markets by the end of the year.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

The Lean Startup by Eric Ries. It changes your thinking on how to build a company. Don’t overbuild; the key is to test and iterate so that you don’t veer off too far in one direction before you know what you’re building and how you should be building it to succeed.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Be a good person before anything. By simply being a good person, you can earn people’s trust, which is critical to building relationships — personally and professionally.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would inspire people to improve the life of older adults everywhere. If we’re lucky, we’re all going to be older adults someday and we should work to build and improve options for the lifestyle that we hope to one day live.

How can our readers follow you online?

You can check us out at www.upsidehom.com or on social media — including Instagram, Facebook and LinkedIn.

This was very inspiring. Thank you so much for joining us!


Meet The Disruptors: Jake Rothstein Of UpsideHōM On The Five Things You Need To Shake Up Your… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

Recommended Posts