#19 Jerry Colonna

11/21/24 • 73 min

Jerry Colonna is a coach, writer, and speaker focusing on leadership, business, and radical self-inquiry. For over two decades, he has proposed that work should be nonviolent to the self, community, and planet. He is host of the Reboot Podcast and the co-founder of Reboot.io, a company founded on the belief that work does not have to destroy us but rather how we achieve our fullest potential.

Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial expertise has resulted in working with some of the largest firms in the U.S. In his work as a coach, he draws on his experience in Venture Capital (VC) as Co-founder of Flatiron Partners, one of the most successful, early-stage investment programs in the New York City area.

Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up and, most recently, REUNION: Leadership and the Longing to Belong.

I invited Jerry into a conversation because of his thoughtful use of questions. We will discuss one of his core questions, which I have used to navigate life and witnessed the power in the lives of others. His unflinching desire to see life's reality, step into all we can become, and call us into belonging is not for the faint of heart, but it results in being fully alive.

Jerry, who focuses on leadership and radical self-inquiry, shares his journey of using questions to navigate and understand the world. Jerry elaborates on his early career as a reporter, where his curiosity and questioning skills began to take shape, transitioning into his roles as a venture capitalist and now a coach. Through sharing personal stories, Jerry delves into the impact of his childhood, his experiences with depression, and his path to becoming a reporter who asked probing questions and tackling subjects that elicited deep emotional responses from business executives. He also discusses historical contexts and systemic issues stemming from fear and curiosity. Additionally, Jerry discusses the importance of remembering and acknowledging personal and communal histories to build better futures. The conversation is rich with insights into how powerful questions foster growth, belonging, and a deeper understanding of oneself and the world.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

Episode Notes

[00:48] Meet Jerry Colonna: Coach, Writer, and Speaker

[02:37] The Power of Questions: Jerry's Journey

[05:07] Liberation Through Inquiry: Jerry's Early Career

[06:48] Curiosity in Journalism: Memorable Interviews

[09:58] The Role of Questions in Personal Growth

[23:59] Exploring Systemic Belonging and Fear

[31:53] Reflecting on Ancestry and Social Responsibility

[40:38] Embracing Difficult Questions

[41:05] Struggles and Inspirations