Jerry Colonna
Jerry Colonna

“The best way to overcome the inevitable loneliness of life at the top may be to connect and mindfully attend to the process that’s already underway – the unconscious sharing that undergirds every relationship.”

Jerry Colonna

Founder, Coach & Facilitator

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 far from the streets of Brooklyn where he was born and raised. He is the father of three amazing humans, each of whom cares deeply about the love, safety, and belonging of others.

Podcast Episodes featuring Jerry

#107 – Reboot: Leadership and the Art of Growing Up – with Jerry Colonna

Episode 107 // June 18, 2019

#107 – Reboot: Leadership and the Art of Growing Up – with Jerry Colonna

In this conversation, Jerry delves into why he wrote the book, opening up about how his life-long practice of journaling influenced the book’s format, and what he hopes those who’ve read the book will gain from their experience.

Lenny's Podcast | Jerry Colonna

Lenny's Podcast | Jerry Colonna

True leadership begins with radical self-inquiry. Jerry shares why team dysfunction often stems from unresolved personal issues, especially those of the leader who holds power.

Tim Ferriss and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck

Tim Ferriss and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck

In his third appearance on The Tim Ferriss Show, Jerry and Tim discuss self-awareness, personal growth, and the complexities of human connection.

#171 – The Great Midlife Edit – with Chip Conley

#171 // April 30, 2024

#171 – The Great Midlife Edit – with Chip Conley

Jerry and Chip Conley ponder the role of an elder and the importance of embracing uncertainty, impermanence, and transition in life. The conversation touches on the significance of emotional intelligence, the three stages of transition, and leaving a positive legacy for future generations.

On Work, Friendship, and Embracing Impermanence | Parker Palmer & Jerry Colonna

On Work, Friendship, and Embracing Impermanence | Parker Palmer & Jerry Colonna

Jerry sits down with friend and mentor Parker Palmer to discuss work and embracing impermanence.

Can You Really Bring Your Whole Self to Work?

Can You Really Bring Your Whole Self to Work?

We still work with the old idea that we should check the messy parts of ourselves at the door of our professional lives. But Jerry Colonna says doing so cuts us off from the source of our creativity. It’s only after we sort through the material of our personal lives that we can become better leaders.

Check Out Jerry's Written Work

The Mask, the Wound, and the Work

The Mask, the Wound, and the Work

We lead best from the places we once feared most. Our leadership becomes an offering, not a performance. Our companies become containers for connection, not compensation for self-doubt. And our work becomes a gift to the next generation.

How Self-Awareness Became The Ultimate Edge

How Self-Awareness Became The Ultimate Edge

In this feature, Jerry Colonna discusses overcoming imposter syndrome, separating self-worth from company success, creating cultures of radical honesty, and the daily practices that prevent founder burnout.

Why Isn’t There More Talk About Ethics in Leadership?

Why Isn’t There More Talk About Ethics in Leadership?

You want to lead well and do the hard things without compromising your values. But there’s no map to tell you how to get there.

What Leaders Can Learn From a Ben & Jerry’s Co-Founder on Putting Your Values First

What Leaders Can Learn From a Ben & Jerry’s Co-Founder on Putting Your Values First

Leaders, it’s never too late to reclaim your seat or to speak out against the things that stifle your voice. In the end, the lives you touch and the company you built are what matter.

For One Who Is Tired of the Fire

For One Who Is Tired of the Fire

Burnout is not a badge of honor. It is not evidence of worth. It is a signal. A signal that you are not meant to be consumed.

An Elder’s Compass: A Guide for Would-Be Coaches

An Elder’s Compass: A Guide for Would-Be Coaches

Coaching isn’t the answer to the question of “What should I do with my life now that my company is no longer operating?’ It is a lifetime’s work. It is a lifetime commitment to being of service.