BRYAN & SHANNON MILES: Leading Through Change and Loneliness episode artwork

EPISODE · Mar 12, 2025 · 57 MIN

BRYAN & SHANNON MILES: Leading Through Change and Loneliness

from The Double Win · host Michael Hyatt & Megan Hyatt-Miller

Entrepreneurship promises freedom—but it also comes with a unique set of challenges that many don’t talk about. In this episode, The Double Win Show welcomes Bryan and Shannon Miles, co-founders of Belay and the nonprofit O’nr, to pull back the curtain on what it really takes to build a thriving business without losing yourself in the process.From hiring their first virtual assistant in 2011 (who later became CEO!) to navigating the emotional weight of selling a business, Bryan and Shannon share their hard-won lessons on leadership, transitions, and making decisions that align with your values.Memorable Quotes“Here’s the magic phrase: ‘In order to be faithful to my existing commitments, I have to say no.’”“I am responsible for myself and my leadership. And I know that if I extend myself too far, I’m not the best version of who I want to be.”“If I’m saying yes to everything and I’m overcommitting and my schedule is absolutely full, there’s no space for creativity. There’s no space for dreaming. There’s no space for new ideas or realizations.”“A lot of business owners are lonely, actually isolated.”“As leaders, part of our job is just kind of to help people settle and know they’re safe.”“Stewardship is just simply managing something for a season of time… While we’re there with our employees and leaders, we’re stewarding our relationships with them.”Key TakeawaysThe Loneliness of Leadership. If you’re feeling isolated as a business owner, there’s good news: You’re not the only one.The Skill of Saying No. Implement this mental shift to help you stop overcommitting without the guilt.Getting Buy-In For Change. What leaders get wrong when making major business changes—and what to do to help your team ride the wave.Living Your Priorities Today. Why Bryan and Shannon took a vacation nine months after starting a business—and the opportunity that followed.The Operator/Owner Difference. Are you owning a business or trapped in it?ResourcesBelay SolutionsO’nrNoFo BrewWatch on YouTube at:  https://youtu.be/pGdaYmIJPHkThis episode was produced by Sarah Vorhees Wendel of VW Sound

Entrepreneurship promises freedom—but it also comes with a unique set of challenges that many don’t talk about. In this episode, The Double Win Show welcomes Bryan and Shannon Miles, co-founders of Belay and the nonprofit O’nr, to pull back the curtain on what it really takes to build a thriving business without losing yourself in the process.From hiring their first virtual assistant in 2011 (who later became CEO!) to navigating the emotional weight of selling a business, Bryan and Shannon share their hard-won lessons on leadership, transitions, and making decisions that align with your values.Memorable Quotes“Here’s the magic phrase: ‘In order to be faithful to my existing commitments, I have to say no.’”“I am responsible for myself and my leadership. And I know that if I extend myself too far, I’m not the best version of who I want to be.”“If I’m saying yes to everything and I’m overcommitting and my schedule is absolutely full, there’s no space for creativity. There’s no space for dreaming. There’s no space for new ideas or realizations.”“A lot of business owners are lonely, actually isolated.”“As leaders, part of our job is just kind of to help people settle and know they’re safe.”“Stewardship is just simply managing something for a season of time… While we’re there with our employees and leaders, we’re stewarding our relationships with them.”Key TakeawaysThe Loneliness of Leadership. If you’re feeling isolated as a business owner, there’s good news: You’re not the only one.The Skill of Saying No. Implement this mental shift to help you stop overcommitting without the guilt.Getting Buy-In For Change. What leaders get wrong when making major business changes—and what to do to help your team ride the wave.Living Your Priorities Today. Why Bryan and Shannon took a vacation nine months after starting a business—and the opportunity that followed.The Operator/Owner Difference. Are you owning a business or trapped in it?ResourcesBelay SolutionsO’nrNoFo BrewWatch on YouTube at:  https://youtu.be/pGdaYmIJPHkThis episode was produced by Sarah Vorhees Wendel of VW Sound

NOW PLAYING

BRYAN & SHANNON MILES: Leading Through Change and Loneliness

0:00 57:35

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

Frequently Asked Questions

How long is this episode of The Double Win?

This episode is 57 minutes long.

When was this The Double Win episode published?

This episode was published on March 12, 2025.

What is this episode about?

Entrepreneurship promises freedom—but it also comes with a unique set of challenges that many don’t talk about. In this episode, The Double Win Show welcomes Bryan and Shannon Miles, co-founders of Belay and the nonprofit O’nr, to pull back the...

Is there a transcript available for this episode?

Yes, a full transcript is available for this episode. You can read the complete transcript on the episode page.

Can I download this The Double Win episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!