Riley Gibson of Silvernest: “Disruption is essential and inevitable, but it’s not always necessarily good”

The two pieces of advice that have always stuck with me are to stay curious and remember to focus more on what you have than what you don’t. Having young children has driven both of these lessons home as I watch them see the world for the first time and learn new things every day. […]

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The two pieces of advice that have always stuck with me are to stay curious and remember to focus more on what you have than what you don’t. Having young children has driven both of these lessons home as I watch them see the world for the first time and learn new things every day. It is a good reminder to keep learning and keep trying to see things as if it is the first time. It’s also important to stay focused on keeping stock on what you have in a world at a time when it is easy to fixate only on what you don’t.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Riley Gibson.

Riley 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.

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?

My dad is an entrepreneur in the tech space and my mom is an artist. I always felt this tension between going the ‘business or engineering’ route or more of the ‘artistic and creative’ route. I thought for the longest time growing up that it was an either-or proposition. Then, I started reading about IDEO and industrial design and taking a design approach to creatively solving problems. It was like a lightning bolt when I realized that those paths could be convergent. I ended up studying entrepreneurship and really focusing on the process of design and design thinking.

Since then, I have worked at agencies, started my own tech company and worked in marketing technology in various leadership roles. This background has given me a broad view of the various business functions, but in each role, I have fallen back on design as an approach to solving problems and it’s proven incredibly valuable. I have also had the good fortune of working alongside some brilliant people along the way.

But something always felt like it was missing. I was doing good work with great people, but got to a point where I was wondering how what I was doing really mattered in the bigger picture. It was during this time that my brother started an incredible mission-driven company called Recursion Pharmaceuticals. They actually have a wall in their office with photos of kids with rare genetic diseases that they are working on finding cures for. It was really in watching my brother where I realized my next step was either finding or starting a company where success meant truly impacting the lives of thousands or hundreds of thousands. When I met Wendi Burkhardt and the team at Silvernest and heard their mission, I knew it was something I had to work on.

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

I think sometimes when we hear the word disruptive, we think of new-to-the-world ideas or groundbreaking technology. Silvernest is taking a very familiar concept — living with roommates — and bringing it to a new stage of life where people often find they have extra space, are socially isolated and are looking for choices to help them earn extra money in retirement. The real disruption for us is in how you reshape the perception of retirement and present modern alternatives that help form mutual opportunity and promote financial stability.

We’ve also using technology to advance the homesharing movement by making the process easier and more protected through compatibility-based matching, background checks, lease creation, insurance coverage and payment processing. Compared with traditional housing listings, it’s proven to be a much more attractive option for aging adults interested in cohabitating.

On a macro level, homesharing addresses increasing crises in our rapidly aging society, such as access to stable and affordable housing and the detriments of isolation. It also benefits the nation’s most crunched housing markets by opening up more affordable room rental options and lessening the need to build more housing inventory.

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 I was starting my first company, I was a year out of college. I got a meeting with Brad Feld who is a very influential VC in Boulder and around the country. When I sat down with him, he asked if I had something he could briefly read about my company and I handed him a document. In it, I talked about building a SaaS company, but had spelled it SAS. It was like this bright window directly into my inexperience in building a software company. He was so nice about it and pointed out the error and ended up connecting me with some incredible entrepreneurs that had deep experience growing SaaS companies. The introductions and conversations that came out of that meeting did more to challenge our thinking and help us work through the business and model than any amount of investment. I think Brad quickly and correctly saw that what we were lacking was not money, but experience and a support network.

I look back on that tiny moment and that tiny but symbolic mistake and it always reminds me that the idea is worthless without execution. Very few good ideas overcome lack of experience, process and a relentless focus on execution, no matter how much funding they get. You won’t know everything, but it is so important to identify your gaps and weaknesses to build a team of mentors, advisors and a board that fill in those gaps and helps you execute.

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?

I am very lucky to come from a family of entrepreneurs, and my father, brother and mother have all been constant sources of mentorship along my path. I remember one particularly pivotal conversation I had with my brother early on a Christmas day as we were on a walk together. He shared how a lot about his mission was to build a truly enduring company that would be thriving a hundred years from now. The way he framed the mindset of building a company has always stuck with me. Amid the pressures of today, it’s easy to lower your gaze and become shortsighted about decisions and what is being built. The exercise of stepping back to understand what you want to build, as well as how that could outlast you or a generation, gave me new perspective.

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?

Disruption is essential and inevitable, but it’s not always necessarily good. Whether disruption in a particular industry is beneficial depends on the perspective of the people, as well as the time period within which you measure its impact. Overall, progress comes with winners and losers, and so disruption can often have a destructive side. That said, if you look at it from a long-term view, the good that has come from disruption is undeniable. The companies I really admire are those that carry a greater purpose and set of foundational principles that are unchanging through time, but that are willing to disrupt themselves and change everything about how they deliver on their purpose.

I do foresee this question around the merits of disruption taking on a new level of importance as we look to the next century. Disruptive technologies such as CRISPR, AI and social media will have immeasurable positive impacts on humanity, but these types of disruptions are so fundamental and widespread that the negative consequences of misuse are things we can’t quite comprehend today. Just look at what is happening with deepfakes, the assault on facts and the mental health crisis in young teens from social media. I think humanity will need to lean hard into a set of values and principles that will help us navigate our way through these changes.

Can you share some of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

The two pieces of advice that have always stuck with me are to stay curious and remember to focus more on what you have than what you don’t. Having young children has driven both of these lessons home as I watch them see the world for the first time and learn new things every day. It is a good reminder to keep learning and keep trying to see things as if it is the first time. It’s also important to stay focused on keeping stock on what you have in a world at a time when it is easy to fixate only on what you don’t.

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

I’m very passionate about the challenges and opportunities around longevity and how we help our older populations age with dignity and choice. I think Silvernest is just getting started as we think about new ways and means of creating mutual opportunity by bringing people together through technology.

We’re also exploring more partnerships with various government entities, non-profits and other organizations to broaden the reach of homesharing and ensure it’s an option for anyone looking to obtain additional income, companionship and assistance finding a compatible housemate. We believe homesharing will be a natural part of every community, and we’re working determinedly to make that happen

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?

Atul Gawande — Being Mortal: The last chapter of Being Mortal reframed a lot of my thinking and motivations for life. After finishing the book, I spent a good amount of time really examining what was important to me vs. what seemed important. What are those things that are going to enable me to die fulfilled and without regret?

Ray Dahlio — Principles: There is a lot in this book I don’t quite agree with, but some of the larger themes really shaped my thinking around building a company. For instance, the importance of seeking truth, of writing things down and of creating principles that can act as a system for making decisions.

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

I think the most influential quote for me comes from Robert Frost: “two paths diverged in a yellow wood, and I took the one less travelled by.” Whenever faced with a big decision, I think about this and it has helped me take a lot of big risks that have made all the difference.

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 am working every day to build a movement around how the sharing economy can benefit our mental health, mobility, financial stability and connectedness. Making homesharing ubiquitous and a more modern approach to aging in place is a big piece of this. Just imagine if 1 million people opened their extra space to others. That could mean 850 million dollars a month in extra passive income for a population that often struggles to make ends meet as life expectancy grows and savings dwindles. That could mean 350 million dollars in monthly savings on housing costs from generating more affordable housing options. This would mean people being able to live closer to where they work, and untold savings in healthcare costs by reducing social isolation.

How can our readers follow you online?

I would welcome the chance for them to follow and interact with me and Silvernest on any of my social channels. You can find us on Twitter at @RileyGibson and @SilvernestLife, on LinkedIn at and, and Facebook at

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