Riley Gibson

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.

Where did the idea for Silvernest come from?

It was the brainchild of Silvernest’s original co-founders. One suddenly lost her father, and her newly-widowed mother was left with the loneliness of her suddenly empty home, so she invited a friend to live with her. That sparked the original idea for a homesharing platform, and the other co-founder helped bring the company to life.

What does your typical day look like and how do you make it productive?

I have learned that my brain is better at certain things at different parts of the day. I like to start early. I need a lot of space to think and process, so I try to protect chunks of interrupted time in the morning where I can really achieve flow. I also try my best to cluster meetings together, so I avoid the 15 or 30 minute in-between times where it is hard to get deep into a task. Finally, late afternoons are the best for me to turn on some music and crank on lots of little tasks and more administrative work.

How do you bring ideas to life?

I’m a student of design thinking and quickly translating ideas into something testable to learn from. It took me a while to learn that ideas are most often wrong in ways that you don’t understand at the beginning, so success is more about the feedback and iteration than the actual idea.

What’s one trend that excites you?

I think we all get carried away with tech, startups and innovation that are geared toward the younger generations, and tend to overlook other age groups. I’m excited about longevity tech and how design and innovation can be applied to some more real and human problems among our aging population to improve their lives.

What is one habit of yours that makes you more productive as an entrepreneur?

I think curiosity is core. I like to read and learn about seemingly random spaces and things, but that often helps me learn and apply lessons from analogies to what I am focused on.

What advice would you give your younger self?

Learn to love process. I definitely fell victim to overfocusing on raw ideas and underappreciating the process and the difficulty of execution.

Tell us something that’s true that almost nobody agrees with you on.

Airplane food is delicious.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Write things down. I think we get so caught up in Powerpoints and presentations where half-thought ideas can thrive. I’ve found the discipline of writing things down forces you to think through details and logic to another level.

What is one strategy that has helped you grow your business?

Placing a focus on clearly articulating a mission and a purpose that has a clear and lasting positive impact. It helps attract the kind of people that want to leave a legacy, and it’s a powerful motivator.

What is one failure you had as an entrepreneur, and how did you overcome it?

It’s hard to pick just one. I think some of my failures early on can be attributed to falling into my own ‘reality distortion field’ and creating and telling a positive story enough times that you start to believe it. When that happens, you start to not face some hard truths and realities about the business. It’s always important to have your eyes on where you are going, but I think fostering a culture where surfacing realities and having a solution-oriented mindset is important.

What is one business idea that you’re willing to give away to our readers?

I have always wanted a mobile app that lets me take a video of my house and all my things and through spatial recognition converts it into an organized catalog for insurance

What is the best $100 you recently spent? What and why?

The 99 cents I spent on a stargazing app for my iPad was the best money I have ever spent.

What is one piece of software or a web service that helps you be productive?

I’m a big fan of MIRO. I use it to facilitate workshops and get the team thinking through problems collaboratively. It is so flexible, and I love that they have opened up a community where workshop and whiteboard templates can be shared. Again, it’s all about the process, so you can learn a lot from different exercise templates like journey mapping, empathy mapping, rapid brainstorming, etc.

What is the one book that you recommend our community should read and why?

I recently read Principles by Ray Dalio. There is a lot I don’t agree with, but some of the concepts I have found very useful. It also reinforced this idea of writing things down.

What is your favorite quote?

“Life is wider than it is long”

Key Learnings:

• Write things down. It forces you to think more deeply and enables others to understand your logic before you ask for their input.
• Ideas are fun, but not worth much. Learn to love process and converting ideas into something that can elicit a reaction that you can learn from as quickly as possible.
• Sometimes reading and researching things completely unrelated to your business can feel like a poor use of time. But, seeking out and learning from analogues and widening your mental perspective is time well spent.