Jerry Colonna

Guest: Jerry Colonna - Co-founder and CEO of Reboot. Jerry is a renowned executive coach and former co-founder of Flatiron Partners, one of the most successful early-stage investment funds. He is also an author and a partner at JPMorgan Chase. Key Takeaways: Radical Self-Inquiry: Ask yourself challenging questions like "How have I been complicit in creating the conditions I say I don’t want?" to evoke personal agency and uncover self-delusions. Equation for Leadership: Practical skills + Radical self-inquiry + Shared experiences = Enhanced leadership and resilience. This framework emphasizes self-awareness and shared experiences over technical skills alone. Impact of Unresolved Issues: Teams often fail not due to lack of talent or strategy but due to unresolved personal issues and patterns from childhood that manifest in group dynamics. Attachment and Suffering: Attachment to outcomes, such as success or material possessions, often increases suffering. Embrace goals for the joy of the journey rather than as a measure of self-worth. Legacy and Purpose: Consider what legacy you want to leave and how you want to be remembered, focusing on meaningful contributions rather than material success. Topics Covered: Radical self-inquiry, leadership development, team dynamics, personal growth, attachment and suffering, legacy and purpose, impact of AI on work, growth mindset.