What does it take to become a fearless leader and sustain performance over decades? In this episode of the Strategy and Leadership Podcast, Anthony Taylor speaks with Brendan P. Keegan, entrepreneur, philanthropist, author of Dare to Disrupt: The 8 Pillars of Transformation, and co-owner of Andretti Global. Brendan’s mission is to create one million fearless leaders, and he brings 25 years of experience as a CEO across six companies to share what it means to lead with courage, build culture, and invest in yourself.
Watch or listen to the full episode below and discover practical insights that CEOs and executives can apply to inspire lasting growth and resilience in their organizations.
Watch the Full Episode:
Key Topics Covered
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Why fearless leadership starts with “the courage to fail and the faith to succeed.”
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How to create a culture that embraces curiosity, accountability, and continuous improvement.
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The role of personal investment in sustaining long-term leadership performance.
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Lessons from sports and business on growth, resilience, and high performance.
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How Brendan’s mission to build one million fearless leaders shapes his work today.
The Courage to Fail, the Faith to Succeed
Brendan Keegan has lived his philosophy of fearless leadership throughout his career. He describes it as having “the courage to fail and the faith to succeed”. From running for class president without popularity to stepping into CEO roles before feeling fully ready, he emphasizes that leaders must embrace the possibility of failure as part of growth.
“Most times, if you put your goals out there, go after them, and learn from your missteps, you’ll end up accomplishing more than you thought possible,” Keegan explains.
Culture as the Foundation of Performance
Keegan highlights that culture is the true differentiator for organizations seeking sustained success. “By far the absolute number one thing is culture. You have to breed a culture that embraces failure, that asks why, and that’s intellectually curious,” he notes.
He stresses that leadership, people, and culture form the first three pillars of his transformation model, and without getting these right, companies cannot sustain long-term greatness — even if they have strong products or strategies.
Investing in Yourself to Lead Others
Keegan believes that leaders must invest in themselves to show up fully for their teams, families, and communities. Once believing that putting himself last was good leadership, he realized that neglecting his health, growth, and energy ultimately hurt those around him.
“Early in my career, I thought putting myself last was leadership. But if you’re malnourished and don’t have the energy to bring food to the table, you’re actually hurting others,” he reflects.
His practices include continuous learning (such as diving into AI years before it became mainstream), maintaining healthy routines, and setting up structured mornings to secure early wins each day.
Lessons from Sports and Sustained Excellence
Drawing inspiration from Tom Brady’s relentless pursuit of improvement, Keegan argues that leadership is a lifetime journey, not a one-season performance. Just as Brady refined his skills even after winning multiple championships, leaders must keep evolving to perform over decades.
“You want to be great not just for one role or one company, but consistently over time. That only happens by investing in yourself and building the right environments around you,” Keegan explains.
“Fearless leadership is having the courage to fail and the faith to succeed.” – Brendan Keegan
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About Brendan Keegan
Brendan P. Keegan is an entrepreneur, philanthropist, and co-owner of Andretti Global. With over 25 years as a CEO across six companies, he now focuses on his mission to build one million fearless leaders. He is the author of Dare to Disrupt: The 8 Pillars of Transformation and founder of The Fearless Experience newsletter, with more than 150,000 subscribers.
Connect with Brendan:
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Website: https://brendanpkeegan.com/
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LinkedIn: linkedin.com/in/brendanpkeegan
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Instagram: @bpkfearless
