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The Reboot Podcast

The Reboot Podcast

Reboot.io 254 episodes Latest May 11, 2026

The Reboot podcast explores the emotional and psychological challenges of startup leadership. Host Jerry Colonna interviews entrepreneurs, CEOs, and startup leaders about their wins, losses, and personal journeys. The show aims to reveal the heart and soul behind building a company.

Episodes

#185 - What If You're Already Enough? - with Grace Belangia & Jerry Colonna Jun 9, 2026 51:39 What does it mean to truly be "okay with being okay?" For many of us, the pursuit of growth, success, and improvement is relentless, often leaving little room for simply accepting ourselves as we are. But what if the real work of adulthood is learning to quiet the inner gremlins, embrace our own enoughness, and build belonging from the inside out? In this episode, Grace Belangia joins Jerry on the
#184 - The End of Suffering Pt. 2 - with Sharon Salzberg, Parker J. Palmer & Jerry Colonna May 11, 2026 50:51 What does it mean to be responsible to suffering, not just the pain we carry within ourselves, but the vast, daily hurt we witness in the world around us? In this rich continuation, Jerry is joined by two dear friends, Sharon Salzberg and Parker J. Palmer, to explore our collective responsibility to one another in fractured times. Together, they examine how the root of so much suffering, personal
Wisdom for Work #31 - Navigating the Neutral Zone: Embracing Change & Transition Apr 7, 2026 41:26 When life upends our expectations, the space between what was and what's next—the neutral zone—can feel like wilderness. It's a time of uncertainty, discomfort, and profound possibility. Yet, how we navigate these transitions shapes not just the trajectory of our personal lives, but the culture and resilience of our organizations. In this episode, Ray Foote joins fellow Reboot Coach Ali Schultz fo
#183 - The End of Suffering - with Sharon Salzberg & Jerry Colonna Mar 4, 2026 01:03:07 When suffering surrounds us, personal, collective, and historical, how do we make meaning without being defined or hardened by pain? In this candid and compassionate conversation, Jerry Colonna invites his teacher and dear friend, Sharon Salzberg, to explore "the end of suffering" and the transformative power of wise hope, compassion, and agency, especially in turbulent times. Rooted in Buddhist w
Extras #27 - Reflection & Intention for the New Year - A Meditation Practice with Marty Janowitz Dec 18, 2025 09:25 One gentle exhale before the blank page of a new year unfolds. Take a moment to settle, reflect, and set intentions with this guided meditation recorded by Reboot Coach Marty Janowitz. You may find this centering practice valuable as you reflect on all that has happened in the past year and set intentions for the year to come. At Reboot, we often use meditation to sit with thoughts, feelings, and
#182 - What AI Therapy Misses: The Power of Human Presence - with Dr. Jud Brewer & Jerry Colonna Dec 16, 2025 01:11:05 What is lost when technology tries to imitate human care? On this episode of The Reboot Podcast, Jerry Colonna sits down with Dr. Judson Brewer, psychiatrist, neuroscientist, and author, to explore the hidden risks and surprising possibilities of AI-powered therapy. Together, they reflect on Dr. Brewer's essay, "The Hidden Danger of AI Therapy," and discuss how chatbots, designed to please rather
#181 - Building The Company That 15-Year-Old You Needed - with Oliver Ravn & Jerry Colonna Nov 25, 2025 51:07 What does it mean to find strength in the midst of suffering, and how can our deepest wounds serve as the roots of profound connection, leadership, and healing? In this episode, Jerry Colonna is joined by Oliver Ravn, CEO and founder of Chronicare, a purpose-driven startup dedicated to building disease-specific peer communities for those living with chronic illness. Oliver reflects on his personal
#180 - Navigating Darkness, Perfectionism, and Purpose as an Entrepreneur - with Melissa Bernstein & Jerry Colonna Oct 23, 2025 53:30 At the heart of entrepreneurship lies not just innovation and ambition, but a deeper journey of self-discovery, resilience, and embracing our most authentic selves. Entrepreneurship, often glamorized for its successes, can just as easily lead us into the depths of uncertainty, loneliness, and self-doubt. Yet, as we face these challenges with open hearts, we discover the possibility for profound tr
#179 - The Work of Getting Free: Redemption, Gratitude & Hope - with Shaka Senghor & Jerry Colonna Sep 9, 2025 01:01:13 In this powerful episode of The Reboot Podcast, Jerry sits down with Shaka Senghor, author, mentor, and leading voice in criminal justice reform, for a tender conversation about transformation, freedom, and what it truly means to be redeemed. Together, Jerry and Shaka explore what it actually means to be free. They discuss how the deepest forms of imprisonment are not always physical, but are inst
Wisdom for Work #30 - The Art of Influence: Building Trust & Connection at Work Aug 14, 2025 36:33 Influence is a force that weaves its way through every layer of our organizations and lives. Yet its true essence, what gives it power and meaning, often lies beneath the surface, quietly shaping outcomes not through authority or force, but through trust, connection, and presence. In this episode, Ali Schultz sits down with fellow Coach Courtney Joyce for a deep and candid conversation about what
#178 - Discovering What Matters in a Distracted World - with Soren Gordhamer & Jerry Colonna Jul 10, 2025 55:12 In a world saturated with distraction and the persistent pull of technology, how do we remember what truly matters? In this episode, Soren Gordhamer, founder of Wisdom 2.0 and passionate explorer of mindfulness in modern life, joins Jerry for a frank and heartfelt conversation about his new book, The Essential: Discovering What Really Matters in an Age of Distraction. Together, they explore the on
Wisdom for Work #29 - Frameworks for Leading & Managing People Jun 20, 2025 38:02 In times of rapid change and growing complexity, how we collaborate and the frameworks we employ can determine whether our teams thrive or falter. In this episode, Ali Schultz and fellow coach Ray Foote discuss the intentional structures that help teams flourish. Together, they illuminate not just the tools available for guiding group dynamics, but also the subtle, often unconscious patterns that

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