He’s Fortune 500 CEOs’ Biggest Secret Weapon (The CEO Whisperer)

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Jerry Colonna is an executive coach, author, and co-founder of Reboot, a coaching and leadership development firm focused on helping entrepreneurs and executives grow through radical self-inquiry. Formerly a venture capitalist with Flatiron Partners, Jerry transitioned into coaching to support leaders in navigating the emotional complexities of leadership. He is the author of the acclaimed book Reboot: Leadership and the Art of Growing Up, which blends personal reflection with professional development. Known for his compassionate yet unflinching coaching style, Jerry continues to influence a new generation of founders and CEOs who believe in leading with authenticity, courage, and heart.

Connect with Jerry! https://www.instagram.com/jerry.colonna/?hl=en
Connect with Ryan! https://twitter.com/RyanJAyala
Connect with Us! https://www.instagram.com/alchemists.library/

Chapters:
00:00 Introduction & Jerry’s Journey to Coaching
01:00 Radical Self-Inquiry & Moral Courage
05:04 Iteration, Growth & Identity
10:17 Depression, Doubt & The Lying Mind
16:12 The Danger of Grandiosity vs. True Confidence
22:06 Masculinity, Role Models & Responsibility
30:02 Redefining Success & Being a Good Man
37:12 Empathy, Mentorship & Leaving a Legacy
43:36 Clean Your Room: Self-Discipline as Leadership
46:05 Redefining Leadership & Followership
50:05 Balancing Compassion & High Standards
56:04 The Buddha of Baseball & Building Extraordinary Teams

Connect with Us!
https://www.instagram.com/alchemists.library/
https://twitter.com/RyanJAyala