Holder of Stories of the Heart: On radical self-inquiry and being a good leader in unsettling times with Jerry Colonna

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Feb 25, 2026

Jerry Colonna, executive coach and former venture capitalist who helps leaders practice radical self-inquiry. He recounts becoming the “Holder of Stories of the Heart” and explores asking “How am I actually feeling?” He discusses owning childhood patterns, relinquishing power to create belonging, sitting with others’ suffering, resisting cynicism, and why kindness and human presence matter in times of upheaval.

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ANECDOTE

Desert Fast That Named His Work

Jerry Colonna recounts a 2008 water-only fast in the desert where he heard the name Holder and became "Holder of Stories of the Heart."
That title frames his coaching: holding people's emotional stories to help them become better leaders and humans.

INSIGHT

Ask How You Actually Feel

Radical self-inquiry means asking "How am I actually feeling?" without pretense or mask.
Colonna calls it radical because socialization trains us to avoid deep questions that threaten safety and belonging.

ADVICE

Ask How You’ve Been Complicit

Do ask: "How have I been complicit in creating the conditions I say I don't want?" to reveal patterns formed to stay safe and belong.
Use 'complicit' (not 'responsible') to invite curiosity over guilt in examining childhood-derived behaviors.

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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: Leadership and the Art of Growing Up by Jerry Colonna

Reunion: Leadership and the Longing to Belong by Jerry Colonna

Siddhartha by Hermann Hesse

Bell Hooks’ poems “When Angels Speak of Love”

REM’s “It's the End of the World As We Know It (And I Feel Fine)”

Jerry’s essay on coaching from an elder's perspective

Connect with Jerry Colonna

Linkedin: https://www.linkedin.com/in/jerry-colonna-reboot/

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 an

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