Larry Weeks

Reboot Part 1: Jerry Colonna On Crucible Moments and Starting Over

Jerry Colonna with Larry Weeks

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When we surface subroutines, when we surface belief systems, we unleash a certain kind of potential, a certain kind of energy that enables us to do the one thing that a leader must do every day – be creative – Jerry Colonna

Jerry Colonna is often referred to as the ‘CEO whisperer.’ Jerry is the co-founder of, an executive coaching and leadership development firm dedicated 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 lead with humanity, resilience, and equanimity.

Prior to his career as a coach, Jerry was a partner with JPMorgan Partners (JPMP), the private equity arm of JPMorgan Chase. Previously, he led New York City-based Flatiron Partners, which he founded in 1996 with partner Fred Wilson, which became one of the nation’s most successful early-stage investment programs. He is also the author of Reboot: Leadership and the Art of Growing Up, which is also the touchstone for our conversation.

There is something about Jerry.

In 2017, WIRED published a piece on Jerry wherein this was written titled “This Man Makes Founders Cry.” I don’t know if it’s how he talks or looks at you, but when talking with him, I felt some sort of sympathetic energy field; it was like a psychic hand on the shoulder. When we spoke, I was dealing with a monster of a cold, coupled with Jerry’s superpower, turned this conversation into a coaching session of sorts.

Jerry talks about leadership and crucible moments, moments that can be transformative, leading to a new or altered sense of identity. These moments often put our character to the test. 

Crucible moments can take the form of a career setback, a personal tragedy, or a major life transition. They are often characterized by feeling “sponged out,” as Jerry puts it, feeling uncertain and vulnerable. However, if faced and reflected on, these moments can lead to profound insights, greater self-awareness, and, maybe, a better place overall. 

If you are in any state of upheaval or change or know someone who is, please listen. Not just for the excellent advice, but there is something beneficial about hearing this level of empathy in someone’s voice.

On the show, we discuss these topics and more …

  • State of leadership currently
  • Why Jerry has a reputation for founders cry
  • Jerry’s story, leaving JP Morgan
  • How leaders can deal with uncertainty
  • The importance of soft skills coupled with hard skills
  • Separating genius from personality
  • Breaking open vs. shutting down
  • What “rebooting” means
  • What do first when you’re laid off
  • Mountain equanimity
  • Work as an opportunity to become better humans



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