Holder of Stories of the Heart: On radical self-inquiry and being a good leader in unsettling times with Jerry Colonna
What if the most radical question you can ask yourself as a leader isn’t about strategy or growth – but simply “How am I actually feeling?”
In this very personal episode, Ben sits down with Jerry Colonna, legendary executive coach, former venture capitalist, and author of Reboot and Reunion. Speaking just days after becoming a grandfather, Jerry brings the full weight of his wisdom as “Holder of Stories of the Heart”—a name that came to him during a water-only fast in the desert—to explore what it means to lead with humanity in increasingly inhuman times.
Resources & References
Reboot: [https://bookshop.org/p/books/reboot-leadership-and-the-art-of-growing-up-jerry-colonna/a4f1b124a9709914?ean=9780062749536&next=t] Leadership and the Art of Growing Up by Jerry Colonna
Reunion: [https://bookshop.org/p/books/reunion-leadership-and-the-longing-to-belong-jerry-colonna/3f3055c88c212fd2?ean=9780063142138&next=t] Leadership and the Longing to Belong by Jerry Colonna
Siddhartha [https://bookshop.org/p/books/siddhartha-a-novel-hermann-hesse/3fc4933ab2f01ae6?ean=9780553208849&next=t] by Hermann Hesse
Bell Hooks’ poems “When Angels Speak of Love” [https://bookshop.org/p/books/when-angels-speak-of-love-bell-hooks/d06b2d33b1c2bfeb?ean=9781451639759&next=t]
REM’s “It's the End of the World As We Know It (And I Feel Fine)” [https://youtu.be/Z0GFRcFm-aY?si=dpBIY6911yNWl--0]
Jerry’s essay on coaching from an elder's perspective [https://www.linkedin.com/pulse/elders-compass-guide-would-be-coaches-jerry-colonna-vzdec]
Connect with Jerry Colonna
Linkedin: https://www.linkedin.com/in/jerry-colonna-reboot/ [https://www.linkedin.com/in/jerry-colonna-reboot/?lipi=urn%3Ali%3Apage%3Ad_flagship3_pulse_read%3BYQenhXg3Tp2vK%2BSe44UDQA%3D%3D]
Bio:
Leadership through radical self-inquiry. This is the driving idea behind the work of Jerry Colonna. For over two decades, he has been dedicated to the proposition that work should be non-violent to the self, non-violent to the community, and non-violent to the planet.
Jerry is a coach, writer, and speaker who focuses on leadership, business, and the practice of radical self-inquiry. He is the Co-founder and CEO of Reboot.io, a company born from the rallying cry that work does not have to destroy us. Work can be the way in which we achieve our fullest self.
A graduate of Queens College, Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial know-how has made him a sought-after coach and leader, working with some of the largest firms in the country.
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. Later, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase.
As a partner with J.P. Morgan Chase, Jerry launched the Financial Recovery Fund with The Partnership for the City of New York, a $10 million-plus program aimed at creating grants for small businesses impacted by the attacks on the World Trade Center.
Along with a strong commitment to the nonprofit sector, Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up (2019) and REUNION: Leadership and the Longing to Belong.
Reboot was met with critical acclaim, stirring up a big question in the hearts and minds of people: "How have I been complicit in creating the conditions I say I don't want?" Jerry's second book builds on this question, asking us what benefit we get from the conditions we say we don't want.
Jerry is astounded by the fact that he lives on a farm outside of Boulder, CO near the foothills of the Rockies, and f
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