The Power of Radical Self-Inquiry for Modern Leaders With Jerry Colonna

Jerry Colonna is the CEO and Co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to helping leaders grow through the practice of radical self-inquiry. A former venture capitalist, Jerry is a renowned executive coach and the author of two acclaimed books, Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. Known for his candid storytelling and exploration of personal and generational challenges, Jerry draws on his experiences as an immigrant, entrepreneur, and leader to help others uncover unconscious patterns and build authentic connections. In this episode… What if the beliefs, fears, and resilience that shape our lives today are not just personal traits, but echoes from generations past? Understanding how ancestors faced change, poverty, and struggles with belonging can transform the way we lead and live. Could reconnecting with our family history reveal where — and to whom — we truly belong? Jerry Colonna, a renowned executive coach and author, tackles these profound questions by tracing his family's immigrant journey and exploring how generational experiences inform our sense of self. Using stories of his entrepreneurial grandfather and the hardships his own parents faced, Jerry reveals how both inspiration and trauma cascade through generations, influencing our choices, leadership styles, and even our capacity for resilience. He shares his personal quest to bridge the disconnections in his own lineage — including a revelatory trip to Ireland to reclaim lost roots, demonstrating how true self-understanding only comes when we look beyond ourselves to our collective past. Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Jerry Colonna, CEO and Co-founder of Reboot.io, about the legacy of generational trauma, belonging, and leadership. Jerry shares candid reflections on family resilience, the illusion of self-reinvention, and how embracing your roots can strengthen both heart and leadership.