Where the Road Bends

#001: Jerry Colonna - The Art of Growing Up

Episode Summary

In this wide-ranging conversation, legendary executive coach, Jerry Colonna, and I talk about why stories unite us, what we can learn from depression, and the 'second adulthood.' We also explore what it feels like when you’re working on something that’s not your calling, how to resist the quiet and discomfort of being alone with oneself, and how to pick up the trail of your life to find clues for what’s next.

Episode Notes


Jerry Colonna – The Art of Growing Up (Reboot CEO & Co-Founder, Author, JP Morgan Partners, Flatiron Partners)

Episode Details

The first guest on Where the Road Bends is Jerry Colonna, the founder and CEO of Reboot.IO, Inc., an executive coaching and leadership firm committed to the notion that better humans make better leaders. He is the author of Reboot – the art of leadership and growing up. He is working on his second book expected to come out this year called Reunion.

He established his coaching practice in 2007. Prior to this work, Jerry was a Venture Capitalist focused on investing in early-stage technology-related startups. In 2002, Jerry became a partner with J.P. Morgan Partners (JPMP), the private-equity arm of J.P. Morgan Chase where he led the firm’s investments in companies such as ProfitLogic Inc. He joined JPMP from Flatiron Partners. With his partner, Fred Wilson, Colonna launched Flatiron in August 1996. Flatiron became one of the most successful, early-stage investment programs. Prior to going into Venture Capital, Jerry worked for ten years for CMP Media Inc. From 1985 to 1993, he served in a variety of roles at InformationWeek, including a three-year stint as its Editor.

Colonna also serves as Chair of the Board of Trustees at Naropa University. It is the only accredited Buddhist-inspired university in North America. He also serves as Chair of the Board of Trustees at the Tibetan Village Project, a not-for-profit, non-political organization dedicated to creating sustainable livelihoods for Tibetans through social entrepreneurship and educational opportunities. He is also a director at the Good Work Institute, whose mission is to educate and connect a network of local community members and actively support their collaborative efforts to regenerate their places. A graduate of Queens College, Jerry lives in Boulder, Colo.

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Where to find Steve Schlafman:

• Website: https://www.schlaf.co/  

• Twitter: @Schlaf

• Facebook: Steve Schlafman

• LinkedIn: Steve Schlafman

Where to find information on Reboot and Jerry Colonna:

• Website: Reboot.io

• Twitter:  @JerryColonna

• LinkedIn:  Jerry Colonna



·   This Week in Startups, June 25th 2013

·   Reboot, Leadership and the Art of Growing Up by Jerry Colonna

·   Let Your Life Speak: Listening for the Voice of Vocation by Parker J. Palmer

·   When Things Fall Apart: Heart Advice for Difficult Times by Pema Chodron

·   Faith: Trusting Your Own Deepest Experience Paperback by Sharon Salzberg

·   Prospective Immigrants Please Note by Adrienne Rich

·   Transitions: Making Sense of Life's Changes by William Bridges

·   Blaise Pascal Quote

·   The Shpilkes - Nervous energy, anxiousness, restlessness

·   Dante’s Inferno by Dante Alighieri

·   Jerry Colonna and Dan Harris: Leadership and the Art of Growing Up

·   Joseph Goldstein’s quote

·   The Paris Review Interview with James Baldwin

·   The Middle Passage: From Misery to Meaning in Midlife by James Hollis


In this episode, we cover:

(00:00) Jerry’s definition on what transition means

(00:25) Jerry’s background as a VC prior to becoming an executive coach

(02:09) How Steve and Jerry met and things that stood out

(03:30) Resonance in each other’s story

(05:40) Jerry’s best and worst days at the height of the dot com era

(07:45) What it feels like when you are working on something that is not your calling

(08:24) Jerry telling Fred Wilson that he couldn’t commit to building another fund

(10:18) Reassessing yourself at the 10-year cycle of working in Venture Capital

(10:57) Impact of 9/11 in reevaluating and reassessing how Jerry wants to live his life.

(12:31) Entering your forties is a transitory period

(12:50) 2/2/2002 – Battling the Black Dog of Depression – Suicide attempt in New York City

(13:50) Taking suicidal thoughts seriously

(14:26) Getting assistance from a therapist

(15:20) A trip to Canyon Ranch; Three books that saved Jerry’s life

(16:20) Meeting and becoming friends with authors

(17:18) Impact that gifts / books can have when you least expect it; the magic of being human

(18:04) Steve’s working on invisible portals into new worlds; A poem by Adrienne Rich

(19:00) Jerry quits JPMorgan Partners at the risk of losing his identity

(21:12) How Jerry found his way to what he wanted to do

(21:30) What the Buddha would have said if he was from Bushwick, Brooklyn

(23:10) Deconstructing Meditation - Resisting the quiet and discomfort of being alone with oneself

(24:03) “All of man, everyone’s problems could be solved if they could sit still”

(25:30) How society defines success – makes being still makes it uncomfortable

(26:30) The Shpilkes – Sitting still is making contact with your true self

(27:28) Society conspiring against sitting still

(28:20) Building your experience through language; name your feelings

(29:45) How frequently little boys cry <> How infrequent adults do

(30:15) Demar Hamlin heart attack in Cincinnati – breaking the myth of men not crying

(31:40) How to pick the trail for your life; where to find the breadcrumbs for what’s next

(33:06) Literature is about transition

(33:36) Resonance of stories - part of the process of growing and growing up

(35:15) Introspection of Steve’s life thread

(37:21) Go back in time into your ancestor’s lineage  

(37:57) Dan Harris – Ruben Museum Conversation

(39:35) Anything can happen at any time a quote by Joseph Goldstein

(41:40) Common themes that give energy and meaning and lead to being fully alive

(42:20) The passing of Jerry’s father – finding realignment

(42:50) Gratitude for meaningful conversations and getting paid to do it – A look into Jerry’s life

(44:02) Passage in new book; referencing James Baldwin and Joseph Campbell

(45:40) Transitions are moments to discover what matters to you and defining that

(46:10) – Teenage years, 20s, and 30s – Transition happens because it becomes unbearable

(48:30) The second adulthood stage

(49:20) – Feeling like you’re in the right body.

(49:55) – Feeling filled to the brim; Steve is young in his second adulthood

(50:50) – End; Sponsor the show, sign up for the newsletter at wheretheroadbends.fm;

Production by Julia Jepsen. For inquiries about sponsoring the podcast, email s@schlaf.co.