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The Reboot Podcast

The Reboot Podcast

Reboot.io 254 Episodes Oct 13, 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

#188 -The End of Suffering Pt. 3: Sitting With What Hurts - with Sharon Salzberg & George Loewenstein
#188 -The End of Suffering Pt. 3: Sitting With What Hurts - with Sharon Salzberg & George Loewenstein Oct 13, 2026 01:00:13 How can changing our relationship to pain transform our lives? In this reflective episode, Jerry is joined by George Loewenstein, Professor of Economics and Psychology at Carnegie Mellon University and author of the book The Opposite of Happiness. Alongside meditation teacher and author Sharon Salzberg, they explore the roots of human misery, blending insights from behavioral economics, psychology
#187 - The Childhood Patterns Driving How You Lead - with Pam Manfredo Curtis & Jerry Colonna
#187 - The Childhood Patterns Driving How You Lead - with Pam Manfredo Curtis & Jerry Colonna Sep 29, 2026 53:03 Who we are as leaders is shaped by the stories we carry and the environments we've experienced. In this deeply heartfelt and introspective episode, Jerry is joined by Pam Manfredo Curtis, CEO coach and author of The Origin of a Leader. With a career spanning 35 years and a PhD in industrial-organizational psychology, Pam Manfredo Curtis brings wisdom earned from coaching executive teams across ind
Reboot Extras #28 - Beyond Mentoring: Exploring the Essential Role of Supervision in Coaching
Reboot Extras #28 - Beyond Mentoring: Exploring the Essential Role of Supervision in Coaching Sep 8, 2026 46:28 How you care for yourself as a coach deeply influences the quality and impact of your work. When we carve out space to reflect on the emotions and patterns coaching activates within us, we open pathways to deeper presence, connection, and transformation—both for ourselves and those we serve. In this episode, Jerry Colonna and Liz Stewart dive into the heart of coaching supervision: what it is, why
#186 - Rewiring Our Relationship With Money - with Michelle Masters & Jerry Colonna
#186 - Rewiring Our Relationship With Money - with Michelle Masters & Jerry Colonna Aug 18, 2026 45:37 What lies beneath our drive for money and success? Is it really about safety, or are we chasing something formed in our earliest years? In this episode, Jerry Colonna is joined by Michelle Masters, author of Wired for Money, as they explore how childhood experiences and inherited patterns shape our adult relationship with money, self-worth, and belonging. With candor and compassion, Michelle share
Wisdom for Work #32 - Beyond the Review: Rethinking How We Talk About Performance at Work
Wisdom for Work #32 - Beyond the Review: Rethinking How We Talk About Performance at Work Jul 16, 2026 52:12 What does it take to create truly transformational workplaces, especially when performance management so often feels transactional or disconnected? In this episode, Jerry sits down with Angela Mckenna, newly appointed coach at Reboot and a veteran in HR, executive leadership, and organizational development. Angela shares wisdom drawn from years inside high-growth companies, examining why performan
#185 - What If You're Already Enough? - with Grace Belangia & Jerry Colonna
#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
#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
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
#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
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
#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
#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

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