047. Jerry Colonna: Why Better Humans Make Better Leaders
RemakeMay 05, 2022x
01:07:05154.02 MB

047. Jerry Colonna: Why Better Humans Make Better Leaders



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.




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.




[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