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 Takeaways

The 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?

Resources

Watch on YouTube at: https://youtu.be/pGdaYmIJPHk

This episode was produced by Sarah Vorhees Wendel of VW Sound

BRYAN & SHANNON MILES: Leading Through Change and Loneliness

The Double Win