About Jerry Colona: Jerry is a coach, writer, and speaker who focuses on leadership, business, and the practice of radical self-inquiry. He is the Co-founder and CEO of Reboot.io, a company born from the rallying cry that work does not have to destroy us. Work can be the way in which we achieve our fullest self. In this deeply reflective conversation, Jerry Colonna — former VC, author of Reboot and Reunion, and one of the world’s most respected CEO coaches — explores the inner journey every entrepreneur must eventually face.
What begins as a discussion about his now-famous out-of-office message becomes a profound exploration of peace, equanimity, grief, identity, and the universal human impulse to return to our true selves. Jerry shares how the high-flying identity of “Prince of New York” once overshadowed the quieter, truer part of him — the poet, the contemplative, the man seeking wholeness rather than achievement.
Through stories of depression, breakdown, meditation, ancestors, and impermanence, he illustrates how inner turbulence and outer success often coexist — and why the real work is learning to return, again and again, to what matters.
https://www.reboot.io/about/coaches
About the Host:
Paul Ryan Paul Ryan is an entrepreneur, mentor, and host of The Inner Entrepreneur. As the creator of The One-Hour CEO and The Life Code, Paul helps business owners design lives of fulfilment, clarity, and balance. His work blends entrepreneurship, personal growth, and purpose.
Work With Paul:
If you're ready to build a business and life that’s aligned, intentional, and deeply fulfilling, explore The Life Code and The One-Hour CEO — coaching and tools for high-performing entrepreneurs.
Connect with the host: www.pauljryan.net https://www.linkedin.com/in/paul-ryan-9a98774/
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