Jerry Colonna

Catch Jerry on Do Radio: Tomorrow's World with Jon Kaye 13-20th October 2025

Jerry is the co‑founder and CEO of Reboot, a leadership coaching company built on the belief that better humans make better leaders. Before that, he was a venture capitalist in New York, co‑founding Flatiron Partners and later working with JPMorgan Partners.

He walked away from that world to explore something deeper: what it means to lead with humanity. His work blends coaching, Buddhist philosophy, and tough emotional honesty. He’s helped startup founders, CEOs, and creatives alike face the parts of themselves that get in the way of good business practices.

He’s also the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong, both part memoir and part manifesto for anyone trying to lead without losing themselves.

Jerry now lives on a farm in Colorado.

Show Notes:

In this conversation, Jon Kaye and Jerry Colonna explore the intersection of technology, personal growth, and the challenges of modern communication. Jerry shares his journey from private equity to becoming a coach, emphasising the importance of aligning one's inner self with one’s outer actions. They discuss the impact of technology on society, the need for critical thinking, and the responsibility that comes with power in the digital age. The conversation highlights the struggles many face in finding fulfillment in their careers and the societal pressures that contribute to mental health issues. In this conversation, Jon Kaye and Jerry Colonna explore the complexities of adolescence, the challenges of information overload, and the importance of fostering community in a fractured world. They discuss the moral responsibilities of leadership, the fight against misinformation, and the hope that technology can bring in connecting people. The dialogue emphasises the human element in technology, the significance of art in creating connections, and the impactful books and quotes that shape their lives.