Brian Doyle is a former Air Force pilot who commanded 31 combat missions before moving into the business world, working at GE Capital, and eventually becoming CEO of Holden Advisors. Today, he helps $100M–$5B companies increase profitability by building pricing strategies that actually get implemented—and embraced—by sales teams.

In this episode, Brian shares how lessons from the cockpit translate to leading in business, from staying calm under pressure to keeping your “cross check” on all parts of the operation. He opens up about navigating COVID just weeks into his CEO role, the dangers of relying too heavily on one client, and why process and discipline are just as important as big ideas.

Brian also talks about bridging generational gaps inside organizations, building trust between sales teams and leadership, and using EOS to keep everyone aligned. Whether it’s negotiating with giants like Amazon or helping companies understand their true value, he explains how to create pricing power without losing customers.

Join us for a candid look at leadership, strategy, and execution from someone who’s flown through turbulence—both in the air and in business—and come out stronger.

In this episode, we talked about:

• How 31 combat missions as an Air Force pilot shaped Brian’s leadership and decision-making.
• Why Holden Advisors blends value-based pricing strategy with hands-on implementation.
• Lessons from rapid growth tied to a single major client.
• Pivoting to virtual delivery weeks into his CEO role.
• Using a pilot’s “cross check” to avoid business blind spots.
• Leveraging EOS to align big ideas with disciplined execution.
• Bridging gaps between sales teams and leadership.
• Adapting communication styles for Millennials and Gen Z.
• Negotiating with giants like Amazon while protecting pricing.
• Connecting with younger generations in a changing workplace.

Brian Doyle's Social Links:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/brianadoyle

Company Website: https://holdenadvisors.com

Links:

Stealth Consulting: https://stealthconsulting.com/

Follow Wesley Mathews on LinkedIn: https://www.linkedin.com/in/wesleymathews/

Skypayments: https://www.skypaymentsgroup.com/