67. Jerry Colonna: How Ancestral Wisdom & Radical Self-Inquiry Can Transform Your Leadership Journey

Today's guest is Jerry Colonna, a leading executive coach who is also the co-founder and CEO of Reboot, the executive coaching and leadership development company, host of the Reboot Podcast, and author of REUNION: Leadership and the Longing to Belong and Reboot: Leadership and the Art of Growing Up.

Drawing on his wide variety of experiences, including his years as a partner with JPMorgan Partners and co-launching Flatiron Partners with Fred Wilson, Jerry shares how he helps clients design a more conscious life and make the changes needed to improve their performance and satisfaction. He explores how our willingness to look honestly at ourselves directly shapes our capacity to lead, to help others, and to be truly present.

Jerry reveals his approach to presence and self-trust, emphasizing that the deepest coaching (and leadership) doesn't come from mastering techniques or performative frameworks. It emerges when we drop the tactics entirely and lean into being fully with another person. He outlines how our unresolved "demons," if left unprocessed, get projected onto the people we lead and coach, and why anyone in a position of power carries a moral responsibility to do their own inner work first. Through candid stories, from his years in psychoanalysis to a vision quest that gave him the name "Holder of Stories of the Heart," Jerry shares his core belief that better humans make better leaders, and that self-inquiry and business results are not in opposition but must be pursued together.

Whether discussing the "hungry ghosts" left behind by disconnected ancestry, the difference between niceness and true kindness, or his own struggle with a harsh internal critic even at 63, Jerry offers a refreshing perspective on leadership that prioritizes authenticity and kinship over ego, control, and "dirty fuel" like fear of failure. The conversation culminates in a powerful reframe: rather than asking "who should I model myself after," the real work is asking who you choose to become, taking in wisdom from your elders while refusing to outsource your own identity to anyone else.