Riley Gibson – Will Older Adults Homesharing Like the “Golden Girls” Be Trending?

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Riley Gibson
Riley Gibson

Riley Gibson
President, Silvernest

Riley Gibson is the president of Silvernest, a unique online homesharing service designed to pair boomers, retirees, empty nesters and other aging adults with compatible housemates. He is responsible for overseeing the company’s strategic vision and day-to-day execution, driving innovation and growth for its technology platform, and creating housing solutions that serve as a model for the future.

Prior to assuming the role of president, Riley was Silvernest’s senior vice president of product, responsible for running a high-performing team through all aspects of the design and development process, as well as defining the go-to-market strategy. 

Riley is a visionary with an optimal combination of business leadership and technological skill. He joined Silvernest to pursue a long-term interest in applying design and technology to solve the nation’s mounting issues surrounding aging and longevity. 

Riley was previously with Kapost, where he led product and design and, following its acquisition by Upland Software, was tapped for a senior position in its $75 million marketing tech business unit. Before that, he co-founded and served as CEO of Napkin Labs (acquired by Chaordix), which built open innovative software for some of the world’s biggest consumer brands. 

Riley has been a contributing author to Fast.Co Design, Harvard Business Review and Inc. magazine, and has a passion for bringing technology and design together to rewrite the rules in mature industries.

Topics of Discussion:

  • Tell us more about the mission of Silvernest and what need you’re looking to fulfill
  • Can you explain how Silvernest homesharing works (walk through process from start to housemate)?
  • What are some specific benefits for homeowners, housemates and the community as a while?
  • Who is homesharing a good choice for and what do people like about it? 
  • Boomers sharing a house isn’t a new concept – thinking about “Golden Girls” 30 years ago. Why is it trending now? Is anything different?
  • Can you share some success stories?
  • Do you see many intergenerational pairings on your platform or is it mainly boomer roommates?
  • Understanding that your solution is for the aging population, what impact have you had in providing this demographic with an affordable housing option?
  • Previously, retirement was about safety, security and hopefully comfort. Are today’s aging adults looking for more? Are they reinventing retirement living?

Riley’s Links:



Hanh: 1:24
Riley Gibson is the president of Silvernest. It’s a novel online home-sharing server, that pairs baby boomers, retirees, and empty nesters with other compatible aging adults. So I’m excited to talk to Riley today about this interesting new solution to prevent the loneliness epidemic facing todays seniors. So Riley, thank you so much for joining me today Boomer Living.

Riley: 1:49
Appreciate it.

Hanh: 1:50
Okay. So can you start by telling us more about the mission of Silvernest and what need are you looking to fulfill?

Riley: 1:59
Yeah. So when I think about Silvernest and our mission I really think about this idea of thriving in place. I think a lot of the industry talks about aging in place, but that seems so narrow and passive and I think, especially for the 50 plus demographic, um there’s so much in terms of connecting fighting social isolation. Our worlds tend to get narrower and narrower, and I think Silvernest really represents another choice, another alternative to be able to stay in your home, increase your income, connect with others and really expand your world. So that’s, again, I think about that concept of thriving in place and how we help connect people to fight social isolation and also just increase income so people have more options later in life.

Hanh: 2:46
Great. I imagine loneliness is a big one. What are the biggest problems Silvernest wants to solve in addition to loneliness you know what else are you helping your users with?

Riley: 2:59
Yeah. So, as you mentioned, the loneliness piece is one. We are also helping with, on one side, creating more affordable housing options for a large demographic, typically home sharing. The cost is 60 to 70% of renting your own place or senior living options. And then, on the other side, we typically see our users are, have less in terms of retirement savings and I think this is a general trend. People entering 65 plus have less and less in savings for retirement, they’re living longer. So the idea the option to be able to turn on $10,000, $15,000 in passive income over the course of the year through home sharing really expands your options in retirement. So, I think it plays into the health side and also the financial stability side in terms of what sharing can offer.

Hanh: 3:49
Let’s go to a little deeper dive of what this entails. So explain how Silvernest home sharing works from a user perspective. What’s the process like from start to finding a housemate?

Riley: 4:01
Yeah. This is obviously constantly evolving for us and something we want to perfect and work on every day. This is our mission to make this experience great, but we have two sides of the marketplace. So you’re either a homeowner and our typical user is 50 to 70, oftentimes they’re divorced or recently had a death of a spouse, so again, they’re fighting that social isolation issue. They can come into Silvernest Get a background screen, post their listing and then we have a unique compatibility matching score that looks for housemates that fit their preferences in terms of what they’re looking for, living style et cetera. And then you can securely message users through our platform and then we actually facilitate the whole lease process and rent process. So we’re trying to make the whole home sharing experience as simple, as seamless as possible. But one thing I’m really excited about is I’ve really challenged us in the team to think about that idea of thriving in place and how we can, yeah, increase the value to our users there. So we’ve really adopted this philosophy of home-sharing harmony and how we can wrap our experience in more kind of services or content or things that help people, you know, connect with their housemate, whether that’s icebreaker questions in the first week or common issues or home sharing agreement to really set standards between the housemate and the homeowner. So really trying to do more to facilitate, not just that matching process, but the whole experience of home sharing.

Hanh: 5:35
So, then what are some benefits, specific benefits for homeowners house mates and the community as a whole?

Riley: 5:43
Yeah. So getting to the community East side, I think, you know there, the good news is there are a lot of options if you are, struggling financially, but you own a home, whether that’s mortgage options or whether that’s Airbnb or others, but some of those come with downsides as well as everything does. I think community-wise home sharing is great because you can typically have a longer term roommate, you don’t have people coming in and out constantly. Our leases are typically nine months to a year. I often meet with people who have been living with the same person for two, three years. So I think in terms of a community, I think there’s a lot of value in terms of more stable home sharing arrangements, and also I think there’s, we see a lot of intergenerational pairings, so it’s not always two older adults living together. We’ve worked with Teach for America, for example, to bring young people who are entering that program who need uh, for more affordable housing options, connect them with older adults And I think things like that can facilitate, um a kind of richer community. So that, I think there’s a lot of benefits on the community side. And then for users, obviously we’ve already talked about the financial benefits, the fighting social isolation, being able to connect with a roommate. I, there’s one story I always come back to, I was talking to a user and I asked her, you know “Why home sharing? How did you come across this?” And she told this story about how, her husband pass away. She felt more isolated, just like her world was getting smaller and she was actually working with a life coach at the time who asked her to just reflect on some of the happiest times that she could remember. And one of those was in college with four roommates just being able to have a glass of wine or just, randomly connect with her roommates through the weekend. That, that was something that was a really powerful experience for her. And so it was this light bulb that there’s nothing blocking her from doing that now. She has a home, she has multiple spare bedrooms with carefully selecting the right roommates, she can really recreate that experience. And that I think was a really cool, powerful story of just the benefits, more of the aspirational benefits of just being, to being able to connect and widening your world.

Hanh: 7:55
Yeah, no, it’s true. I think, as we progress in the later parts of life regardless of the level of acuity or relationships that we have with our loved ones, if we’re blessed enough to have those folks in nearby, or perhaps if we’re not, but I’m hopeful that whether it’s a society, family, friends, I don’t want to say fill that gap, but it’s providing a continuation of life, right? A continuation of life where, like you said, “It isn’t over.” If you have a loss of a spouse, a loved one, perhaps your community, your relatives, whomever that is, a roommate, for instance, can, can be instrumental a continuation of your life that did allows you to do some of the activities that you once did. So I think it’s wonderful. It’s really all about continuing to live and live to the max that you can whether it’s senior living, middle age, it’s about living and maxing out your life. So I think it’s a great idea.

Riley: 8:54
Thank you. Yeah, I, someone a lot smarter once said to me, life is a lot wider than it is long, and that really stuck with me and I think oftentimes as we think about senior living, this category, there’s been a focus on longevity and length of life that is this mentality of “Do no harm”, I think is great. We’ve lengthened our lives, but I think we’ve lost a bit of focus on widening our lives, aspecially in those later parts. And so I’m proud to be part of something that is really thinking about how we give people options when they’re often at a stage of life when doors feel like they’re closing or they’re becoming less connected. I think as a society, we need to get more creative and innovative about how we help people live a wider life and you experience more. I think this stage of life can be the greatest stage of growth not something where we’re just stagnant and aging in place. Yes.

Hanh: 9:50
Absolutely. I agree. I love the idea of continuing of life regardless of your relationship with your loved ones, a loss of a spouse, perhaps, or children that are farther away, a decline of acuity, for instance, regardless of where you are in there. I love to be in an environment that lends itself for me to continue to live and thrive and engage and live with a purpose. So, I hope that is the direction that we’re all are heading to and I believe we are, and I am hopeful that we’ll continue to be. This solution is only targeted to certain groups of people, not for everybody. So who is home sharing? a good choice for and what do people like about it?

Riley: 10:34
Yeah. As a brand, as a company, we obviously very much focused on the 50 plus market, but I think we see more and more opportunity in terms of intergenerational pairings, things like that. We’re definitely not exclusive in terms of who can leverage the platform. But we see often on the homeowner side, as I mentioned, they’re typically 50 plus folks who have home have extra space, again, kids have gone off to college, they own their home, but are, would like more in terms of financial flexibility, financial stability. I think that is, is a great example where home sharing can can be a great option to just boost passive income, again, create that connection. So that’s typically you see who we see on the homeowner side and then the housemates side or the renters side we see a much broader set of individuals that I think this is a good option for. There’s, we know across the country, affordable housing and more affordable housing options are a huge issue. So I think it is a great option for people who, are looking to live closer to work. We see a lot of people who are in service year programs or, Teach for America, for instance where this is a great option to be able to come in and have access to a great living situation, closer to where they’re working. So, I think there’s a lot more kind of option on the renter side for where this can be a good fit.

Hanh: 11:57
Older adult sharing a house isn’t a new concept. Just think about the “Golden Girls” 30 years ago. So why do you think it’s trending right now and is there anything different?

Riley: 12:07
Honestly. Yeah, it’s always been a bit perplexing to me why it seems like a new idea, again, as you mentioned, “Golden Girls”, it, as you graduate college, it’s expected that you’ll live with a roommate. That’s how you get by and get your start. So, it’s always been surprising to me that when you talk about home sharing at this stage of life, there’s this light bulb of, “Oh, I’ve never thought of that as an option.” I’m not sure why that is, but our mission is to normalize that as much as possible. And I think, it’s obviously everyone has their kind of progression of life and expectation and, I think home sharing is, feels unexpected sometimes of it as an option, you think about moving into just senior living or other options. But I think that’s our goal. That’s our mission is to make it feel as normal as it was when you graduated from college and just expected to have a roommate. But it’s, yeah, it’s always been interesting to me that it feels like such a new thing. And there’s this light bulb moment when you talk to people about the idea, the concept, cause it’s been around for so long it’s it’s not a new idea.

Hanh: 13:11
Can you share some success stories that you’ve seen with Silvernest?

Riley: 13:15
Yeah. So I think I, that is one of the coolest parts about, being in this role and working with this company is just, as you talk to users, all the different stories that you hear. You know, there’s a lot of stories of, as I mentioned, someone losing a spouse, just feeling depressed, loss of income with that event and just their life isn’t moving in the direction they expected. And I love hearing the stories where then finding a roommate, whether it’s through Silvernest or other programs or moving in with a friend, that became this sort of light bulb that, I think changed their life and allowed them to be more social, gave them more income to start to go on trips that they couldn’t have afford before. I think those are such cool stories where people, again, to come back to that concept of widening your life, someone starts to home share, and then they have so many more options in terms of the things they can do and the people they can do them with.

Hanh: 14:12
Great. So, do you see many inter generational pairings on your platforms or is it mainly baby boomers and parents and grandparents, roommates?

Riley: 14:22
Yeah. So, I think it’s increasing more and more. and so, I think about 20% to 25% of our pairings end up being intergenerational. but as I mentioned, more of what we’re doing in terms of partnerships and other programs are really focused on, nonprofit service year programs getting those individuals who typically are younger, giving them more affordable housing options. So, we really see more intergenerational pairings as a cool growth opportunity. And I think there’s so many benefits of intergenerational pairings. I think sometimes in senior living we have this eggs, age segregation that I, can be unhealthy at times and I think you get stuck again in, in your world. And so I really think there’s a lot of advantages to having more intergenerational pairings. Through our platform you can cite whether you want help around the house and things like that. So you can, be more independent if you have a, someone that’s younger who can help with chores, yard, work, things like that. So again, it just unlocks a lot of opportunities. But as to answer your question, it’s about 20% to 25% that are intergenerational currently.

Hanh: 15:31
Okay. Understanding that your solution is for the aging population, what impact have you had in providing this demographic with the affordable housing option?

Riley: 15:41
Yeah. So, there’s lots of ways to measure that. I think one of the ways we measure is just sort of the income, the extra income that we can bring our users and also the savings in terms of housing that we can bring. And we have this ambitious goal for ourselves that by 2030, we want to have, be facilitating a million home shares and that would bring approximately $800 million a month in terms of extra income that this demographic would be earning and about $300 million a month in terms of saving or more affordable housing options. So I think, we want to set our sights high and I think home sharing just in terms of purely the financial side of it can bring incredible benefits, just to extra income and savings for more affordable housing options.

Hanh: 16:29
So previously, it was about safety, security, comfort, are today’s aging adults looking for more and are they reinventing retirement living do you think?

Riley: 16:40
I certainly think so. And I think the market is behind on delivering that, but, you know, I luckily see so much innovation in the space. Every day there’s new, cool ideas that I see coming to market that are really, I think, bringing new opportunities to connect this demographic to lifelong learning opportunities, new housing options, we’re not the only one bringing sort of new housing options to market. So I think this demographic the boomer population will completely reinvent the aging experience. But I think the market is catching up and is a bit behind, I think we’ve, over-focused on, on other generations and bringing innovation and technology and services to that group. So I’m really excited to see what the next 10 years will bring and I think things will look very different to what they do today.

Hanh: 17:29
Yeah, I think so too. I think COVID has obviously had its tragedies, but it’s also opened up many innovation across many sectors, I think, especially senior living. So I am excited as well. So now, what do you think is your biggest strength that enables you to have a unique, impactful effect on older adults, maybe something that isn’t well known about you?

Riley: 17:50
I think one thing that is a challenge, but also, a benefit or a strength is just, we are a younger team and I think we have, a lot of experience just in terms of creating figital solutions technology. The hard piece about that is, oftentimes we make assumptions in terms of what, what would make sense to a user in terms of our experience that doesn’t necessarily make sense to this demographic. So I think, one of our strengths is how we can bring new technology, new interfaces, and new offerings to this demographic. But I think we need to really be careful on how we test that from a user perspective, to make sure that it is as accessible as possible. Oftentimes I think we can make, again, assumptions in terms of what will be a logical flow that isn’t always true. So that, I think another piece of that is just having a true kind of “Don’t Know Mind” of really approaching everything as if we’re looking at the interface for the first time and involving our, our customers and our users and helping craft and build that experience so that it makes as much sense as possible, as intuitive as possible. And that’s something we will always be working on that’s never finished.

Hanh: 19:05
So, do you think working closely with older adults has changed you in any way?

Riley: 19:09
For sure. I, again, I think the simple answer there is you can, before this, I worked in marketing technology running product and design and, you can get very focused on the new, the cool and how to bring new things to the interface, how to leverage the newest pieces, um, of technology. I think moving to this space has really refocused and reset myself and the team on just creating the best possible outcome. And really again, involving our users and helping us understand, what makes the most sense, what is the best in terms of the experience? So I think it is, it has, opened my mind and really helped focus me on just really crafting experiences for an outcome and not getting caught up in just the new, the cool, the best necessarily.

Hanh: 20:02
I’m thankful for this opportunity to learn more about you and your company. Do you have anything else that you would like to share?

Riley: 20:09
I Appreciate the time. This was great. Thank you.

Hanh: 20:12
All right. Take care.

Riley: 20:13
Yeah. Thank you so much. It was nice to meet you.

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