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

Send us Fan MailJerry 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/RyanJAyalaConnect 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 TeamsConnect with Us!https://www.instagram.com/alchemists.library/https://twitter.com/RyanJAyala