1: How to find out your customers’ pains to build a scalable product – with Jake Rothstein from UpsideHom

Today’s guest is Jake Rothstein, the CEO and founder of UpsideHōm, whose mission is to enhance the quality of life for older adults everywhere. Jake had previously co-founded Papa, a company which pairs older adults and families with ‘Papa Pals’ for companionship and assistance with everyday tasks.

Jake Rothstein is the founder of UpsideHom and Papa – startups focused on solving senior adults’ challenges.


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  • KK:

    We’re live from Warsaw and somewhere in Florida, right?

  • JR:
    We are in sunny South Florida.
  • KK:

    Awesome. So hey, Jake, I’m really excited to have you here today.

  • JR:
    It’s great to be here.
  • KK:

    I’d like to discuss scaling with you when it comes to startups, as you have started at least two companies that I know of. Before we start the discussion about pains and customers, I would like to ask you what’s UpsideHōm status at the moment?

  • JR:
    Sure. So, just a bit of context, UpsideHōm is building the biggest senior living community in the world without laying a single brick. We have just raised our seed funding round of just a little over $2 million. We’re super excited about that. We have some really fantastic investors on board, and went through a pretty rigorous fundraising process, even in today’s environment. Now, we’re hiring talent in key areas, and we’re preparing ourselves for scale. We’re building the processes, and systems, and protocols in order to enable that imminent scale. That’s the phase that we’re in now. We’re operating tightly in the south Florida area. We’re building a marketplace business in a sense. It’s really important for us that we maintain geographic relevance at the beginning while we continue to work out a lot of the processes and systems that we will ultimately need to scale.
  • KK:

    How does it differ from the usual senior living facilities?

  • JR:
    What’s unique about us is we’re utilizing existing infrastructure. We work with professionally managed, amenity rich, apartment operators. These are traditional multifamily operators. We’re able to leverage their infrastructure in order to create a disaggregated, senior living community and do it in a more easily scalable way. So, we utilize existing infrastructure on the multifamily apartment side. Then we utilize existing service infrastructure to be able to provide flexible services to our older adult residents if and when, and only if they need them. Our approach is very individualized, it’s very customized. That’s what our customers are coming to us looking for.
  • KK:

    So, on one hand, you integrate what’s already on the market. On the other hand, those senior living facilities are not actually senior living facilities because there are other people living there. So, it feels more natural for the residents, right?

  • JR:
    Exactly, they’re inherently intergenerational buildings. One of the things that we learned in my prior startup was that there’s this tremendous amount of power to creating intergenerational relationships. Over the last 20 or 30 years, maybe more, we’ve been, as a society, segregating people by age. Maybe doing it consciously, or subconsciously, or whatever it was. We were building facilities out in the suburbs where land was cheaper. We were putting our older adults in society in those types of places to age, what we thought, was gracefully.

“Prior to startup, there’s this tremendous amount of power to creating intergenerational relationships”


  • KK:

    It’s great that you remind us about that because that’s how we have lived for a long time. And now, as you said, we usually put those facilities out of sight in the suburbs.

  • JR:
    What we’re finding is that there’s so much missing as a result of age segregation. Our goal is to bring generations back together; bring them back together in the same communities, so that in our building you can have an 85-year-old that’s living next to a young couple with little kids. That’s powerful and that’s important, that’s special for both of those people.
  • KK:

    That’s a big shift. You mentioned that we’re a bit segregated, or apart. How did you learn about the pains of senior adults? How can you know your customer?

  • JR:
    That’s a great question. My experience in this industry started with my first company called Papa. Back in 2016, 2017, my grandfather was diagnosed with Alzheimer’s. My grandmother, who was 82 at the time, was trying to care for him. It was really challenging for her as an 82-year-old, to care for your husband that you’re seeing lose his memory and losing who he was. It was challenging for her, and it was challenging for the family to watch that.  She would oftentimes call me in a crunch and say, ‘Hey, my friends are calling me, they want to meet me at Starbucks. Can you come just watch your grandfather for a little bit so I can get out of the house?’ She just really needed a break.  My grandfather didn’t need a caregiver because she was his caregiver. She was helping him go to the bathroom, shower, and eat. She needed a babysitter for him. She needed someone that was warm and compassionate, and that was the grandson. She called me, and she knew I would come at a moment’s notice, that I’d drop everything. I was a salesperson on the road at the time and so, I did this for a while. She would call me weekly, and it got very challenging for me to continue to do that with any kind of regularity.  I remember calling a few traditional home care agencies. There’s a whole industry around caring for people in the home. I had a simple request, ‘Hey, can you send someone at a moment’s notice to come babysit my grandfather? He doesn’t need care, we just need someone as a companion, to keep an eye on him. Maybe play some cards or watch some TV with him’.
  • KK:

    Someone humane, who sees him as a human being.

  • JR:
    Exactly, exactly. Which was few and far between. I called five places. I recall this vividly. Of the five places I called, five of them laughed me off the phone. They’re like, ‘Sorry, we can’t get someone over there within 60 minutes, or within two hours. And even if we could, you would need to get put on a regular schedule. We have to send out a nurse to do an evaluation. It would be a minimum of 20 hours a week that you’d have to commit’. My grandmother’s life doesn’t work that way, that’s not how it works. When her friends call her, they’re going to Starbucks now. They want to come meet her. She needs to get out of the house. I’m like this is really crazy. I remember, I called my cousin Andrew. I’m like, ‘Andrew, this is really interesting. There are 20 million college students in the country and many of them are looking to become healthcare professionals or health related professionals. Everyone in college is looking for extra part-time work, flexible income, right?’ This was 2016, the gig economy was really starting to take off. Everyone was talking about the Uber for this and the Airbnb for that. We’re like, ‘Let’s build Uber for grandkids. Let’s just see if we can build the grandkids on demand’. And so, we called it Papa. I quit my job and we started the company. That was the entry point; building a company that connected young adults that needed flexible work and older adults that needed a little bit of companionship and assistance with basic tasks, not care, what they call IDLAs, the instrumental daily living activities. Fast-forward five years, Papa is doing 1000s of visits a day across the whole country. It’s really been a knockout success. We learned a lot about this population in building that business, especially in the early days. People are really lonely, and loneliness is a tremendous epidemic. It causes all these major negative health outcomes. When we started putting our heads together about UpsideHōm, we saw this amount of loneliness that was out there, and we said, ‘How can we build in companionship?’ We’re sending, we call them ‘Papa Pals’, we’re sending a Papa Pal into a person’s home a couple times a week. That was alleviating loneliness and building companionship for those couple hours a week. How can we take that to the next level? How can we really truly build in companionship? The initial concept for UpsideHōm was a completely shared approach. It was to build Golden Girls’ houses. Let’s get single family homes in the suburbs, and we’ll put three older ladies in them that otherwise would have lived alone. We’ll make it really, really easy. We’ll manage everything for them. We’ll get housekeeping, we’ll put cable and internet in the house, we’ll you know about activities in their area. And that’s what we did. We rented a house in the suburbs. It was really challenging to say the least. Our landlord was in another country, and it was hard to get in touch with him. The floorboards were coming up, the pool was leaking, and the roof was leaking. We couldn’t get anything fixed. We’re like, ‘Oh my God, how are we going to do this 10,000 times? How does this scale?’ And that’s when we started working with traditional multifamily apartment communities that had the scale that we needed on the supply side and also had a lot of the manpower on the ground to help us with things like maintenance.

They had the scale that we needed on the supply side and also had a lot of the manpower on the ground

  • KK:

    You mentioned that you started with your own experience. I guess that was easier to see the actual pain from your grandmother and grandfather. I hear from founders who are working with senior adults, that it’s more complex, or more demanding to actually find a focus group to do interviews with them or to actually help them open up to them to talk about those pains. So, how do you go about it?

  • JR:
    That’s a great question. I think that one of the things that makes this demographic that we’re catering to very unique, different from millennials and Gen Zs, is that they are not immediately trusting. They, it takes a lot to build a trust with an old, to build the trust with an older adult. The unique thing about that, though, is that once you’ve built it, once you’ve earned that trust, they really trust you, and you keep it unless you do something really, you know, egregious to lose it. What we’ve focused on from the very beginning is how do we build trust with our prospects, and or customers? How do we start that trust building from that first interaction that we have with them? Whether it’s the content on our website, the podcasts that they might be listening to, or whether it’s how they engage with our salesperson when they first answer the phone. Building trust with people is really important. You’re only going to start getting true, unbridled feedback from them once you have that trust. People are hesitant to give you their real opinions, especially when you’re building focus groups and things like that. I’d say trust is probably the most important thing. And, it takes time, effort, and grit to build that trust with this audience.

You’re only going to start getting true, unbridled feedback from them once you have that trust

  • KK:

    Once you build this trust, what’s your process to ensure you’re constantly up to date with their needs? I guess they change over time.

  • JR:
    Absolutely, one of the really unique things about this customer is that they grow with you. Every customer essentially grows with you, but we anticipate having our residents living with us for a long time. People don’t want to move a lot once they’re 75 or 80. To answer your question, I think meaningful engagement is really the most important thing for really understanding what the needs and wants of our customers are. What I mean by meaningful engagement is, are we being proactive about engaging our customers with things that are of value to them? Are we making them smarter about the things that are around them? Are we helping them engage better in the community? And are we helping them make friends and increase the quality of their life and wellbeing? It takes a very proactive approach to do that. We don’t want to be reactive. You can’t be reactive with this customer. When you’re really trying to please older adults, you really have to go above and beyond from an engagement standpoint. Our model makes it so that people are coming to us because we’re the provider of the roofs over their heads, we control the maintenance, we help them get food, and we help them get rides to doctors. Because we’re able to control all of these different things for them, and do it in the background, we’re helping them get these things done, they trust us, and they come back to us. And they open up to us. We believe we can provide a lot more value once that happens. The relationship continues to grow and the value that we’re able to provide continues to grow alongside that relationship.

Meaningful engagement is really the most important thing for really understanding what the needs and wants of customers are

  • KK:

    You start with trust, then they start relying on you because as you said, you provide a roof, but you also provide groceries, or a ride to the doctor. They can rely on you as a service, as a company, or as a human being that helps them with that. I guess you put together all the data points and you analyze where the needs are right? What’s the story behind that? If something can’t be measured, does it mean it doesn’t exist?

  • JR:
    Yeah, that’s exactly right. At the beginning, this is very anecdotal. How many people are on average asking for groceries or for rides to their doctors? At the beginning, you really have to start thinking about how you aggregate data. How you’re collecting information in an anonymized way, but that will be ultimately very helpful for the customer. That really helps us make decisions. All the decisions that we try and make in the business are data driven. We don’t want to be flying by the seat of our pants, and our customers are sharing a lot with us. We want to make sure that we’re doing things in a way that’s really creating value and that there’s data behind the decisions that we’re making. I’d say that it’s important to structure that properly and to do it from the very beginning so that you can measure. What is success if you’re not measuring against some sort of baseline?

We want to make sure that we’re doing things in a way that’s really creating value and that there’s data behind the decisions that we’re making

  • KK:

    True. My last question about pain here; pain of our customers is actual pain. You said in one of your interviews that you see loneliness as a medical concept, this sounds really interesting to me.

  • JR:
    I’m not the only one that’s thinking about loneliness as a sort of a healthcare problem. If you look at the Medicare Advantage landscape, and the Centers for Medicare and Medicaid, and how they’re thinking about loneliness these days. It’s evident in Papa’s business, certainly, but it’s evident in everyone’s eyes now, and it wasn’t five years ago. Loneliness is truly one of the most social determinants of health. If you can reduce loneliness among an at-risk population, you can improve health outcomes meaningfully. Which means you can improve cost on the backend. Instead of being really reactive to issues that arise as a result of loneliness, like anxiety, and depression, and all these different negative consequences, you can treat loneliness at the root, and sort of alleviate all those things on the back end, which is really great for everybody. It’s good for society, the health care system, for the cost, and the taxpayer. And it’s not just loneliness, it’s food insecurity, housing insecurity, and companionship. You know there’s loneliness and there is social isolation, right? You can be in a room full of people, and you can still be lonely. And you can be completely socially isolated, which we’ve all felt in the last 18 months or two years. But you don’t have to be lonely if you’re socially isolated as long as engagement is proper and correct, and you’re doing it in a meaningful way. It’s more complex than it sounds. It’s not just like, ‘Okay, let’s solve loneliness, and everything’s going to be happy’. There’s a lot of moving parts in determining health outcomes for people that inevitably will have them.
  • KK:

    That’s the sad part. I’m happy at least there’s someone taking care of that now so when I’m there, I know I can rely on those services as well. Let’s move on to the product itself. How do you see the role of technology in those businesses directed at seniors? How does building such a product differ from building something for millennials or Gen Z?

  • JR:
    It’s a great question, and it’s a complicated answer. One of the things we learned at Papa early was that you can build the best app in the world and if nobody downloads it because your demographic or audience is not familiar with using apps or not comfortable with using apps, then it doesn’t really exist. If a tree falls in the forest, and you’re not there to hear, it doesn’t make noise? At UpsideHōm, we have to be very aware of our customers’ ability to use technology and what kinds of technology they’re able to use. Observation in the early days is very important. Giving customers optionality and how they’re going to engage with you, is really important so that you can observe where they’re most comfortable. You can observe sort of what the baseline technology that they’re willing to use. What I mean by that, you have to provide a variety of different access channels. If a customer is comfortable with texting, give them the option to text you. If a customer is comfortable with picking up the phone, give them the option to call you. Use technology however you see fit in order to streamline efficiencies and to drive leverage in the business. Eventually, that changes. The 65-year-old of today, looks different than the 65-year-old of 10 years from now. The 75-year-old today looks very different than the 75-year-old of 10 years from now. So, you have to always be forward-thinking about what the customer is going to look like in 10 years. We are thinking about building technology that’s going to enable that customer 10 years from now while still allowing multiple access channels today. Maybe 10 years from now, the average 75 -year-old will have no problem using an iPhone app or an Android app. But today, that’s not the case. Today, there’s some people that are 80 that have flip phones, and that’s all they know and understand, and they don’t want to learn anything else. I think optionality is really important in dealing with this demographic. I think it will always be important because there’s always going to be the next new technology. Ten years from now, the iPhone app may seem antiquated. An 85-year-old might not want to use the hologram in their eyelid that orders groceries for them. I think we’re always going to be this type of conversation, and we have to build for the moment but think about what the future looks like as well. Which is an interesting balance. Technology is never built; it is always being built, and that’s an important thing to realize. When you hire big engineering teams and spend a lot of resources on tech, it’s never, ‘Okay, here’s my product, and it’s done’. It’s, ‘Here’s my product, and this is what it looks like today, and it’s going to look different tomorrow, and it’s going to look different in a week from now, and a year from now’.

“Giving customers optionality and how they’re going to engage with you is really important”

“Use technology however you see fit in order to streamline efficiencies and to drive leverage in the business”

  • KK:

    That’s definitely a good point. As you mentioned, it evolves. So, I wanted to ask you, what’s your value proposition at the moment? And has it evolved from this year or even from January to today?

  • JR:
    I think it’s an ever-evolving value proposition. Our value proposition is different depending upon who you’re engaging with, and who you’re talking to. One of the things that makes the sale complex when you’re selling things to older adults, is that they’re not the only decision makers in many cases. A lot of times their adult children, or maybe a family member, younger family members, are helping them to make these decisions. That’s not because, necessarily, they need that help. It’s because they want that help, they’re engaging their family members to help them make these decisions because either don’t want to make these alone, that they shouldn’t be making these types of decisions alone, or they just really want their advice. Our value proposition is different to the older adult child than it is to the older adult themselves. We are a second set of eyeballs for the adult children. We’re another safety net. We enable a de-stigmatized environment that their parents can grow with and grow into, that could be geographically relevant to where they’re living. We have a lot of customers moving near their kids. They don’t want to be in their kids’ homes, but they want to be near them. And they don’t want to be in a traditional institutionalized environment. That’s the value proposition for the older adult children. There are so many things for the older adults themselves. Our model is so flexible, some people find value in the idea of intergenerational community, or in the idea that they can age in the right place, and they don’t have to move 15 times. If they’re declining in health, causing them to have to look at other options, they may not have to if they stay with us. Cost is a value. We’re selling something that’s a little bit less expensive than what is maybe otherwise available in the market. We have a lot of optionality for that. So, the value proposition is different for every customer because of the flexibility of our model. It’s also different for the different buyer personas that we deal with on a daily basis.

“Our value proposition is different depending upon who you’re engaging with, and who you’re talking to”

  • KK:

    Marc Andreessen once said that product market fit means being in a good market with a product that can satisfy this market. You have a product that can satisfy the market. Do you think it’s a good market? Is it something that we should bet on?

  • JR:
    I would say, unequivocally, yes. It’s a tremendous market. Almost unquantifiable big. Eleven thousand people a day are turning 65 in the US alone. Aging on its own is a $7 trillion market in the United States, and a $22 trillion market globally. We’ve never seen a demographic shift like this in the history of the world. And so, I’d say, is it a good market? I’d say it’s the best market we’ve ever seen anywhere at any time in history. You can probably be blindfolded in this market and hit a billion-dollar opportunity without even trying. It all comes down to execution. There still needs to be a lot of work that has to be done to extract value out of this market, and a lot of value has to be provided. This is a discerning customer. They’ve been around for a long time and know what they like and don’t like. They have their opinions, and they’re happy to share them, in most cases. And so, understanding the market and its size is important, but because there’s so much opportunity, focus is really a challenge. You can go in so many different directions with this customer; you can sell them so many different things that provide value to them and that can add to your bottom line. But without focus, you could wind up chasing your tail a lot.

“For entrepreneurs or founders trying to get into, or in the early stages of being in this market, focus is critical.”

  • KK:

    What are those one billion opportunities that you see in the market that are still to be unveiled or built on?

  • JR:
    We’d have to schedule another few hours to go over all the market opportunities, even at a high level. I’d say healthcare for older adults is broken. People have been building point solutions forever in healthcare. And digital health is buzzy right now because COVID has accelerated a lot of that buzz. But point solutions are just that, they solve one or two problems. There’s not an infrastructure that allows all of these points solutions to be delivered efficiently. And I think people that try and innovate in healthcare find it a struggle. How do you get things out to people? How do you solve more than one or two problems at a time? How can you actually lower costs? How can you actually solve these big systemic problems with small point solutions? We’re looking at building the platform to deliver a lot of different best of breed point solutions to older adults as they need them. And obviously collect a lot of data around that, as we do it.
  • KK:

    You previously co-founded Papa, and now you’re building UpsideHōm. Having had experience into senior oriented companies, and building to senior oriented products, what are your biggest lessons learned from that process?

  • JR:
    I’d say never make assumptions about your customer and what they want. Observe them. I think that it’s one thing when Steve Jobs came out with the iPhone, it was like, ‘Okay, this is what people want, whether they know they want it or they don’t know, they want it, this is what people want, and they’ll buy it’. And sure enough, he was right about that. I think it’s a little bit different when we’re talking about selling things or making things for older adults and things that they want. You can be prescriptive to some extent, and you should be. But there’s also a lot of observation that has to happen. You have to see how people are going to engage with you in order to build the products that they really want. You can think that you know what to build, you can think you know what they want, but until you’ve actually engaged with them and interacted with them and done it with some level of repeatability and consistency, it’s very hard to know. Everyone’s a little bit different. I’d say, don’t have any preconceived notions about your audience, or about what they want. Just observe them and the truth will come out in doing that. I think that’s a big takeaway. The other big takeaway in this market, is customer acquisition is very hard. Customer acquisition is hard in any business, in any market, but this is particularly hard. It’s particularly hard, because you have a variety of decision makers. These are big life-changing events. People are a lot of times frazzled by big decisions at this stage in life. I’d say the takeaway from that is, build the trust. Work to build the trust first, and the sale becomes easier. Work to build the value first, and the sale becomes easier. If you do all of those things, and you’ve got the right product, because you’ve observed the customer, the sale just happens. My background before all of this is in enterprise software sales and there’s truth in that, in that sale as well. If you’ve educated the buyer right along this buyer’s journey, and you’ve done a good job at feeding them the right content and making sure that they’re smart about the industry and about their options, if you’ve done everything right, the sale just happens at the end. And that’s what separates a good salesperson from someone that might not be so good. But have a good product, make sure you educate the customer the right way, and it’ll happen.
  • KK:

    I hope lots of sales happen for you naturally. I know you’re still very early with UpsideHōm, but when we met last year at Techstars Longevity Program, I think you were just about to open your first facility for registration and now you have 120. That’s impressive and that’s why I would like to go into this topic of scaling. How do you go about scaling the locations? You’re still focused on Florida, but I saw on the website that you’re looking to expand pretty quickly.

  • JR:
    Yeah, scaling is, the fun part, right? You have to make sure that your ducks are in a row before you actually step on the gas. I’d say one of the biggest learnings that we’ve had at UpsideHōm and at Papas, before you pour too much fuel on the fire, make sure that your foundation is poured correctly. Because when you try and scale and everything else isn’t ready, things break. If you can avoid that, then better. Ultimately things will break in a startup. If it’s hyper growth there’s always going to be things that break. Every time a team doubles, you wind up with new management, management challenges and things like that. But in terms of scaling, you have to have a model that inherently is scalable. You know exactly what your inputs and outputs are, and you have to constantly be thinking about customer acquisition costs and your lifetime values of your customers. If you have those two things in mind with everything that you do and you’ve built the foundation to be ready to step on the gas when you can, those are the things you really need to be conscious of as you’re doing it. There are periods of a business where it’s always going be a little scary to step outside of the that comfort zone. It’s like, ‘Okay, we’re small still, but we really need to get big, let’s get bigger’. But you got to just sort of close your eyes and do it and make sure that you prepare yourself well for it. Have the talent in place ready to go. The reason we’ve been able to scale so fast at UpsideHōm is because we brought on really incredible talent that has experience doing it previously. It’s nice to not have to train someone from the ground up.
  • KK:

    How do you do that? Building a startup that, even though it’s scaling pretty fast, it’s still not a well-known brand, so how do you attract really good people? You just said, you have a great team that knows how to do those things. Because if you bring inexperienced people at the very beginning, even if they are very devoted to the cause, it can literally kill your business. So how do you build a team in a company that just starting and does not have many success stories yet? How do you find and hire the best people?

  • JR:
    The first thing I’d say to that is that you have to have a mission driven company. Both of the companies that I’ve been involved with have been very mission driven, they’re personal, and the story is real. This is about my grandparents. I wake up every morning, I think about my grandmother, and I think about my grandfather. Telling that story, authentically, attracts people. It’s relatable, everyone has a grandparent or a loved one that’s an older adult that they can sympathize with. If people can buy into the mission, then it’s an easy sale. It’s really key, especially for the first team members were in a startup. You’re not paying market rates for talent. You’re paying a little bit below market rates, because you have to figure out how to make do with less. And so, part of it is really making sure that you believe in the mission and vision and that you can do well and do good at the same time and convey that message to the earliest talent.
  • KK:

    How do you come up with a mission? I’ve seen lots of bigger companies run workshops together with their management team and after years of research, come up with a mission. What was your process here?

  • JR:
    Ours was sort of organic because it came from a personal need. UpsideHōm was born from not only learning from Papa, but because once my Papa passed away, my grandmother was on her own. She was living in this big two-story house that they lived in together. She had just had knee replacement surgery, so she couldn’t walk up the stairs. And she was lonely. She didn’t know how to pay her bills by herself. We were all helping her do that, and it was a pain. She didn’t drive at night anymore. So, when she wanted to go to one of the family member’s houses for dinner, I’d go and pick her up and drive her there. She’s living in this big house, loves her neighborhood and loves her community. She’s made a lot of friends there. She doesn’t want to leave the community. But this is not the right house for her anymore’. And so, we moved her into a smaller apartment in the same neighborhood. She was still close to her doctors, her book club, and to her friends. I acted like what we now call the home manager. I was the guy that helped her pay her rent every month, fix her computer ran out of batteries, and when the cable box needed to be reset. I’m like there’s got to be a lot of people like her. She’s not alone here. She’s not just alone in being recently widowed and in needing help with a little these extra things. She still bathes herself, eats, and cooks, but it’s these little things that under normal circumstances family is able to help with. Certainly, in modern times, it’s more and more challenging for families to do that. They have their own kids to handle. They’re living in a different geography. Their parents are somewhere in another state or country. That was what sparked it. My grandmother was alone and probably didn’t want to be alone if she doesn’t have to be. She’s got a lot of friends that are also living in apartments by themselves. I thought, ‘What if we just match them up? And what if we help them do all these little things, would that be valuable?’ And turns out, it was. We’re seeing every day that it’s valuable to a lot of people. And so that goes back to the mission driven.
  • KK:

    It’s definitely very personal and it sounds really true. You don’t have to convince many people with that. You just tell the story and it’s there. For scaling, you need the locations and the team, but also fundraising, right? Funds are an important part of this. Do you have a plan for that? Did you sit down and say, ‘Okay, that’s when we need the pre-seed, that’s when we need our seed, and this is what we have to do to get series to series A?’

  • JR:
    Yeah, absolutely. You have got to plan for everything. In the startup world, everything is based on milestones. You have this big vision to take over the world, and you have to bite it off in chunks. Taking over the world is a pretty gargantuan task. Building software that’s going to do everything that you needed to do is a really big task. You need a billion dollars and a team of a thousand to do it. So, it all has to be chunked up and broken up into certain milestones and timeframes around those milestones. It’s good because it holds the team accountable to certain key metrics and key things that we’re driving for. It helps everyone be aligned and understand what are the tasks that need to be done in order to hit these objectives. Once those objectives are hit, can we unlock more capital, as an example, to help us scale further? Can we unlock more resources to help us get better talent? To answer the question, in short, yes, it requires a tremendous amount of planning. When you raise capital, you have to understand what you’re going to do with that capital. Investors won’t be very happy if your capital just sits in the bank, or if you’re burning cash, and it’s not creating growth, or it’s not being used to create the foundation to have growth eventually. It’s a process, raising capital is very similar to a traditional sales process. There’s a pipeline. There are investors that are qualified, just like leads that are qualified. Then you move people along the process. Running a tight fundraising process is one of the really important things in building a startup that you plan to scale.
  • KK:

    So, you shared how you look at having the right team and how you look at the fundraising, but then how do you prepare yourself to scale? There are so many things that you’re doing for the first time as a founder while you scale.

  • JR:
    Sure, I think there’s a lot of ways that I personally do it. Number one, make sure that you’re getting exercise regularly. Be in the right mental state to make decisions. Use decision-making frameworks that makes sense for the business. I recently listened to a podcast that shared about a decision-making framework for startup founders, that there are two different types of decisions. There are decisions where the door closes behind you after you make the decision there’s no going back. Then there’s the decision where it’s like a rotating door, and you can just go right back in the same door you came from. It’s a much easier decision to make. Those types of decisions, with rotating doors should be made very quickly. Decisions in the startup world have to be made very quickly, especially as you’re teeing up for scale. The decisions where you can’t go back should be a lot more thoughtful and given more time. I try to look at everything in context, is it a long term-decision that we have to really think hard about? Or is it a decision that we could just easily pull back if it’s the wrong one? There’s plenty of decisions we make that are wrong, and that’s okay. You have to be willing to accept that you’re going to be wrong half the time, or maybe more than half that time. Depending on your luck, maybe less than half the time. Preparing for scale, you need to be healthy. You need to have the right support system in place, and that is support at home and on the business side. Make sure that you surround yourself with advisors that make sense for the business. One of the most challenging things for me, is getting really fantastic advice from lots and lots of people. I think that we saw this going through the Techstars program. We met a tremendous amount of really smart people that all had their own opinions about everything. And then when you go through the fundraising process, you meet a lot of really smart investors that have their own opinions about everything. And it’s challenging to take all of that feedback in and then try and make decisions. Part of it is using that decision-making framework. The other part is keeping your ears open to people that might know more than you in order to help make good strategic decisions for the future of the business. There are people that maybe have never built this specific business before, but there’s pattern recognition. If you’ve seen 100s or 1000s of businesses, you can see trends. And so, keeping your eyes and ears open for those things, and being willing to listen, test, try and iterate is really important when you’re preparing and in the process of scaling.
  • KK:

    I really like that you start with yourself and your health and that you have to take care of yourself. I see a lot of founders that forget about that and that’s when everything starts to crack is when the founders are not really there mentally or physically. Please everyone, remember to sleep, eat well, exercise, and then go and work and build your company. My last question, what’s a piece of advice you would give to a person who’s just starting their company?

  • JR:
    That’s a loaded question. If I had to pick one thing, build a company that you really care about. If you don’t care about it that much, and you’re just doing it because you think there’s a big opportunity, good luck. You have to really truly, honestly, believe it in the depths of your soul. Because it is hard. It is really, really hard and it takes a lot out of you. If you’re not really passionate about what you’re building, you can’t give it the grit and hustle. You can’t give all the business needs, especially in the early days. If you don’t have that passion and driving fire inside to keep trying to figure out this problem you’re trying to solve, then pick something else. I’d say just be true to yourself.
  • KK:

    Okay, so now we go back and say, ‘Okay, you have to sleep, eat, exercise, and then be passionate about what you’re doing’. And that’s how you start basically.

  • JR:
    Yeah, I think that’s a good starting point.
  • KK:

    I think it’s a good final point as well. Thank you, Jake, for being here and sharing your experience. Good luck with your next business, or businesses.

  • JR:
    Great, thank you so much. It was such a pleasure doing this and I’m excited for the next one.

Thank you for listening. If you want to learn more about Jake and UpsideHōm, visit www.upsidehom.com. You’ll find the link in the podcast description. 

If you enjoyed our conversation, subscribe wherever you’re listening from to get updates on the newest episodes. 

Kasia

Summary

Finding your customers pains, product market fit and prepare for scale of a new startup can be daunting. On today’s episode, Kashia explores the widespread concern of loneliness, isolation and unaffordable housing options for older adults with UpsideHōm’s CEO and founder, Jake Rothstein. With a mission to enhance the quality of life for older adults everywhere, UpsideHōm provides solutions to tackle these challenges at scale.

Jake takes us through his personal journey of how he discovered the pains for seniors, the importance of building customer trust and the process to ensure the company is constantly up to date with the ever-changing customer’s needs.
With two successful business launched, Jake shares how important the foundation at start-up is key to early success. New businesses do not have historical data to guide them on decision making. An experienced team ensure your company is ready to scale at the right time with a clear mission, vision and value proposition.

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