047. Jerry Colonna: Why Better Humans Make Better Leaders

08/03/23 • 67 min

TODAY'S GUEST

Jerry Colonna is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm whose coaches and facilitators are committed to the notion that better humans make better leaders.

For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others to lead with humanity, resilience, and equanimity. He’s been called the CEO Whisperer and the Coach with the Spider Tattoo, and has taken refuge in the Buddhist dharma tradition.

Previous to his career as a coach, he was a partner with JPMorgan Partners (JPMP), the private equity arm of JP Morgan Chase. And before that, had launched Flatiron Partners with partner, Fred Wilson. Flatiron became one of the most successful, early-stage investment programs in the New York City area.

Today, he lives in Boulder, Colorado.

EPISODE SUMMARY

In this conversation we talk about:

COVID, and how it exposed the interdependence, but also the inequality of American society.
Leadership in the context of the Ukraine war, and how when leaders don't address their vulnerable and wounded parts, that expresses itself in violence. We discuss that in the context of malignant narcissism with Putin, and also with Trump.
His childhood, and how he became keenly aware of how people around him are feeling.
His career in venture, and how he veered from that into coaching.
My therapy session, where he points his radical inquiry, his coach mind, at me.
My tendency to hide, to not want to be very active on social media, at least not publicly on Twitter.
My fear of being judged, and my fears of not being seen or appreciated.
What it means to bring your whole self to every challenge in your life, at work, and at any other moment.
How everything is an opportunity for self growth, and to practice that.
His reboot system and method, and his book.
How everybody in life is basically looking for love, safety, and belonging.

We had this conversation in mid-March 2022, and that was two years into the worldwide outbreak of COVID, and a couple of weeks into Russia's invasion of Ukraine. I was excited and nervous to talk to Jerry, who's famous for making podcasters cry. We also had a brief chat months before preparing for this interview and I already had a taste of his radical inquiry approach to coaching.

So as expected, this did not end up being a regular interview. While we got to explore his history and his ideas and his childhood a little bit, Jerry turned his radical inquiry on me as expected. And you'll get to hear a pretty detailed coaching/therapy session on this podcast and dive deeper into my fears and insecurities along the way. I have to say, I found it deeply therapeutic, both at the time, and now weeks later when I relisten. This was a very different, very meaningful process for me, and I hope that you'll find it beneficial as well. It definitely affected the way that I approach putting myself out there and allow myself to be more visible on social media.

Shortly after this interview was recorded, I definitely did start being more vocal and an amazing thing happened. As I started being more vocal on Twitter and other platforms, we got more and more downloads for this podcast and the podcast started growing very, very rapidly. And so I owe a big thank you to Jerry for challenging my assumptions and helping me pinpoint these insecurities. Jerry assured me that this is helpful to other people to hear. So I really hope that will prove true, and that you'll find this episode really helpful to you in your journey as well.

This conversation with Jerry is one of a dozen or so weekly conversations we already have lined up for you with thinkers, designers, makers, authors, philosophers, entrepreneurs, and investors who are working to change our world for the better. So follow this podcast on your favorite podcast app, or head over to remakepod.org to subscribe.

And now let's jump right in with Jerry Colonna.

TIMESTAMP CHAPTERS

[6:58] Life During Covid

[13:23] The War in Ukraine

[20:51] Early Childhood Empathy

[24:25] A Journey to the Venture World

[32:54] A Therapy Session

[52:17] Business as a Tool for Growth

[57:44] Bringing Your Whole Self

[1:00:20] The Reboot Approach

[1:05:01] A Short Sermon

EPISODE LINKS

Jerry's Links
- 🌎 Reboot.io
- 📘 Reboot: Leadership and the Art of Growing Up
- 💼 LinkedIn:

TODAY'S GUEST

Today, he lives in Boulder, Colorado.

EPISODE SUMMARY

In this conversation we talk about:

COVID, and how it exposed the interdependence, but also the inequality of American society.
Leadership in the context of the Ukraine war, and how when leaders don't address their vulnerable and wounded parts, that expresses itself in violence. We discuss that in the context of malignant narcissism with Putin, and also with Trump.
His childhood, and how he became keenly aware of how people around him are feeling.
His career in venture, and how he veered from that into coaching.
My therapy session, where he points his radical inquiry, his coach mind, at me.
My tendency to hide, to not want to be very active on social media, at least not publicly on Twitter.
My fear of being judged, and my fears of not being seen or appreciated.
What it means to bring your whole self to every challenge in your life, at work, and at any other moment.
How everything is an opportunity for self growth, and to practice that.
His reboot system and method, and his book.
How everybody in life is basically looking for love, safety, and belonging.

And now let's jump right in with Jerry Colonna.

TIMESTAMP CHAPTERS

[6:58] Life During Covid

[13:23] The War in Ukraine

[20:51] Early Childhood Empathy

[24:25] A Journey to the Venture World

[32:54] A Therapy Session

[52:17] Business as a Tool for Growth

[57:44] Bringing Your Whole Self

[1:00:20] The Reboot Approach

[1:05:01] A Short Sermon

EPISODE LINKS

Jerry's Links
- 🌎 Reboot.io
- 📘 Reboot: Leadership and the Art of Growing Up
- 💼 LinkedIn:

Previous Episode

006. Kathy Davies: Design Your Life to Get Unstuck

TODAY’S GUEST

Kathy Davies wears many hats - she’s a Design Lecturer at Stanford University. She's the Managing Director of the Stanford Life Design lab, where she and her team have trained 150 universities globally to use the life design processes on their campuses to help students design, prototype, and test the right career paths for them.

She is also a Cofounder and CEO at DYL Consulting where she uses design thinking and life design principles to build a better world.

EPISODE SUMMARY

In this episode we discuss:

[02:56] Challenges during the pandemic, transitioning into virtual classes and workshops.
[18:34] Kathy's early desires to connect, and to combine science with art in her work.
[29:23] Kathy's engineering experience.
[33:14] Getting into Design Thinking at Stanford.
[48:59] The journey into Life Design.
[1:02:22] Why is it so hard for us to figure out what we want to do in life?
[1:07:31] The Life Design process.
[1:19:39] Life Design for women.
[1:30:02] The future of Life Design, and its impact.

EPISODE LINKS

Kathy Davies' Links
- 🌍 Stanford Life Design Lab
- 🌍 DYL Consulting
- 🌍 Stanford Product Design Program
- 📘 Designing Your Life Book
- 🌍 Designing Your Life for Women
- 🗓 Designing Your life for Women Event Page
Other Things Discussed
- 🌍 Seth Godin's Akimbo Workshops
- 📺 How to Make Hard Choices, TED Talk by Ruth Chang

ABOUT US

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Next Episode

026. Rabbi Amichai Lau-Lavie: Community, Ritual, and Creativity

TODAY'S GUEST

Rabbi Amichai Lau-Lavie is an Israeli-born, Jewish educator, writer, and performance artist. He's the creator of Storahtelling, Inc. and the founding spiritual leader of Lab/Shul in NYC, an artist-driven, everybody friendly, God-optional, pop-up experimental community for sacred Jewish gatherings.

Amichai is a member of the Global Justice Fellowship of the American Jewish World Service, a founding member of the Jewish Emergent Network, serves on the Leadership Council of the New York Jewish Agenda, the Advisory Council of the International School for Peace - a Refugee Support Project in Greece, a member of the Advisory Council for the Institute for Jewish Spirituality, and is a faculty member of the Reboot Network.

Through all his endeavors, he brings a creative, inclusive, and vital energy to Jewish practice and Jewish life.

EPISODE SUMMARY

In this conversation we talk about:

How the Jewish concept of the set table served both as a happy early memory, and as an organizing principle for his later work.
How Covid 19 made rituals and online communities more important than ever.
His orthodox roots as the scion of an ancient and respected rabbinical dynasty, and his journey of self discovery through theater, drag, and art.
His creation of storytelling, a way to bring to life the ancient ritual of the reading of the Torah, and the Maven Method he developed to spread the practice further.
The emergence of Lab/Shul and the community around it.
The power of spiritual design and a well-designed practice in transforming our lives and our communities for the better.

We also discuss:

How is religion used as a tool in the service of humanity?
What happens if you bring scripture to the 21st century as a performance?
Why is the tribal wisdom of small circles within a bigger circle so important?

I've long believed that one of the most promising avenues to apply design skills and creativity to is in designing communities, social rituals, and spiritual practice that suits the modern world. And, as such, there's no one I can think of that exemplifies this better than Rabbi Amichai Lau-Lavie. I think this conversation, which is full of wisdom and fun, is a great introduction to exactly the type of spiritual design we need to see more of. So let's jump right in with Rabbi Amichai Lau-Lavie.

TIMESTAMP CHAPTERS

[3:52] Life During Covid

[10:17] The Wisdom of the Set Table

[22:31] The Birth of Storahtelling

[29:55] A Paradigm Shift from Patriarchy

[38:25] Rebirth of the Translator

[54:34] The Design of Lab/Shul

[1:00:19] Design Thinking and Virtual Practice

[1:11:54] Individualism vs Collectivism

[1:19:36] The Significance of the Tree

EPISODE LINKS