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

1. “Here’s the magic phrase: ‘In order to be faithful to my existing commitments, I have to say no.’”
2. “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.”
3. “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.”
4. “A lot of business owners are lonely, actually isolated.”
5. “As leaders, part of our job is just kind of to help people settle and know they’re safe.”
6. “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

1. The Loneliness of Leadership. If you’re feeling isolated as a business owner, there’s good news: You’re not the only one.
2. The Skill of Saying No. Implement this mental shift to help you stop overcommitting without the guilt.
3. 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.
4. Living Your Priorities Today. Why Bryan and Shannon took a vacation nine months after starting a business—and the opportunity that followed.
5. The Operator/Owner Difference. Are you owning a business or trapped in it?

Resources

• Belay Solutions
• O’nr
• NoFo Brew

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

This episode was produced by Sarah Vorhees Wendel of VW Sound

We all know that habits shape our lives. But which habits actually matter? In this episode of The Double Win Show, Michael and Megan sit down with Dr. Andrew Abella, founding dean of the Bush School of Business and author of Superhabits, to discuss a framework for building a flourishing life. Andrew shares how ancient wisdom, backed by modern science, reveals the core virtues that drive success—and how anyone can develop them. If you’ve ever wondered where to start when it comes to personal growth, this episode is your answer.

Memorable Quotes

1. “Cultivating self discipline is not about stifling a desire. It’s about redirecting it gently into a more productive direction.”
2. “There is a specific set of habits that is far superior.”
3. “Vitrues are specific habits of excellence.”
4. “Every [virtue] all of us have inside us. They just need to be activated… by practicing them.”
5. “There’s a freedom that comes from growing in self-discipline, because instead of being a prey to whatever desire that you have, you’re in charge.”
6. “For an adult who’s looking at harmless social media, the problem is you are wasting your desire to know on stuff that is not going to help you.”

Key Takeaways

1. The Four Pillars of Success. Prudence, justice, courage, and self-discipline form the foundation of a flourishing life, shaping how we think, act, and grow.
2. The “Which Habit?” Problem. Most habit books focus on how to build habits, but the real challenge is knowing which habits will lead to lasting success.
3. The Power of Restraint. Simple acts of restraint—like pausing before reacting or delaying instant gratification—build your no muscle for the other areas of life.
4. The Role of Leisure. True rest isn’t about doing nothing—it’s about engaging in activities that refresh the mind and restore creativity.

Resources

1. Superhabits by Dr. Andrew Abela
2. Superhabits Substack
3. GrowVirtue (The SuperHabits App)
4. The Anatomy of Virtue Graphic
5. Andrew Abela’s LinkedIn

Watch on YouTube at: https://youtu.be/RAJeu68fIJ4

This episode was produced by Sarah Vorhees Wendel of VW Sound

In this episode of The Double Win Show, Michael and Megan sit down with bestselling author Jay Papasan to talk about the secret to extraordinary success: focus. Jay unpacks why most people struggle with distraction, how to create an environment for deep work, and why small, consistent actions lead to massive results over time.

Memorable Quotes

1. “Our focus muscle depends on how long we’ve been using it and how much distraction we have to deal with every day.”
2. “If it’s important enough, it belongs on my calendar.”
3. “When you get really good at your one thing, you don’t just get many results. Your impact gets larger and larger over time.”
4. “Extraordinary starts this way: It starts small and it grows so much faster than we can imagine.”
5. “There’s two groups of people in life: doers who don’t have space to dream and dreamers who don’t have space to do.”
6. “It creates anxiety and fear because it matters. We don’t want to fail at the things that matter most to us.”
7. “Our culture rewards busy people who move fast and get things done.”
8. “It should always be situational. When do we need to be fast? When do we need to be slow?”
9. “If you’re going to do something extraordinary, it’s not going to be because you did millions of things. It’s going to be because you did that thing and the handful of things that matter around it extraordinarily well.”
10. “Everything in life that matters happens pretty slowly.”

Key Takeaways

1. The Focus Bunker: How to design a workspace that protects your attention so you can do your best work
2. The Domino Effect: The science behind tiny actions that lead to exponential growth
3. The Myth of Busyness: Why getting a lot done doesn’t mean you’re moving forward (and what does)
4. The Value of Slow: How taking your time can actually speed up your success—and why the best things take time
5. Rituals for High Performance: Small habits that make big results inevitable (and how you can implement them today.)

Resources

• The One Thing by Gary Keller & Jay Papasan
• The One Thing Podcast

Watch on YouTube at: https://youtu.be/UnMEk4qAJcw

This episode was produced by Sarah Vorhees Wendel of VW Sound