Elevate with Robert Glazer Elevate Classics: Jerry Colonna on Building A Meaningful Leadership Legacy
Dec 11, 2025
In this enlightening discussion, Jerry Colonna, CEO of Reboot.io and bestselling author, dives deep into the essence of meaningful leadership. He shares how childhood experiences shape our leadership styles and the importance of inner work. Jerry reveals his journey from venture capitalist to coaching, highlighting the significance of compassion and resilience. They explore the pitfalls of seeking external validation and how true fulfillment comes from understanding 'enough.' This conversation emphasizes the necessity of inquiry and accountability in leadership.
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Boardwalk Turning Point
- Jerry ran away as a teen and spent a night under the Coney Island boardwalk, which became a turning point for him.
- He declared then that his current life would not be his life and used that intention to change course toward success.
Mentors Changed His Trajectory
- Mentors and teachers rescued Jerry multiple times, including a therapist and a professor who awarded a scholarship.
- Those interventions led to internships, promotions, and ultimately a career path into venture capital.
Grow Up To Lead Well
- Better humans make better leaders because leadership requires grown-up inner work.
- Compassion for people you disagree with is part of mature leadership, without becoming a doormat.
