BRYAN & SHANNON MILES: Leading Through Change and Loneliness
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Mar 12, 2025
Bryan and Shannon Miles reveal the real challenges of entrepreneurship, including the loneliness that often accompanies leadership roles. They discuss the importance of prioritizing relationships while navigating the complexities of business and family life. With insights on decision-making, they emphasize finding balance and creativity by learning to say no. The couple shares valuable experiences from their journey in founding Belay and highlights the significance of mentorship and community in overcoming feelings of isolation as business owners.
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question_answer ANECDOTE
Vacation Opportunity
Bryan Miles shares how a vacation led to a pivotal business opportunity with Michael Hyatt.
A tweet during their trip resulted in a surge of leads for their company, Belay.
volunteer_activism ADVICE
Saying No
Reflect on big opportunities before accepting them, especially considering time constraints.
Get comfortable saying "no" or "no, not now" to avoid overcommitment.
insights INSIGHT
Abundance Mindset
Saying "yes" to everything can lead to burnout and ineffectiveness.
Focusing on abundance rather than scarcity can make saying "no" easier.
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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?
The Double Win