Jerry Colonna changed my life as a leader.
I first met Jerry at his CEO Bootcamp in the Colorado Rockies in 2015. As a newly minted CEO, I joined a small group of founders hosted by Jerry and his team on a stunning ranch. It was my first coaching experience.
Those five days profoundly shifted my trajectory as a leader. It's difficult to capture exactly what happened there, but I began learning how to lead from the heart, not just the head.
Jerry and I became friends. His books, Reboot and Reunion, have deeply touched me and many of my friends. When I stepped down as CEO of Makers in 2020, I chose to train as a founder coach myself, inspired by his impact.
Later, Jerry generously wrote the foreword to my book, Startup CEO Succession, sharing reflections from our journey together. In this special conversation, we explore CEO successions, why pursuing wholeness matters more than chasing happiness, and why inner work is a lifelong adventure.
Enjoy the episode!
Timestamps
(Clickable on Youtube)
00:00 Introduction
02:32 Over-Identification with Work
07:23 True Self and False Self
15:00 This Suffering is Avoidable
27:28 "I'm 61. It took 60 years, you know?"
33:59 Wisdom Practices
40:04 Love, Safety and Belonging
48:22 Letting Go vs Giving Up
53:10 Standing Still When Your Hair Is On Fire
56:14 Challenges That Are Not Ours To Face
01:00:25 Successful CEO Transitions
01:09:07 Final Reflections
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