The Reboot Podcast

Hosted by Reboot.io

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255

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Jun 2026

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About the show

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEOs, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

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60 recent

June 9, 2026Episode 18551 min

#185 - What If You're Already Enough? - with Grace Belangia & Jerry Colonna

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 podcast for a second time to discuss rejection, self-worth, and the courage to create community. Together, they explore the importance of building one's own table of belonging and how courageous conversations can transform both our inner and outer worlds. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

May 11, 2026Episode 18450 min

#184 - The End of Suffering Pt. 2 - with Sharon Salzberg, Parker J. Palmer & Jerry Colonna

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 and systemic alike, lies in our refusal to acknowledge the truth of our interconnection. When we turn away from that truth, we don't escape pain; we deepen it. But when we find the courage to move toward what frightens us, to walk into otherness rather than away from it, something remarkable becomes possible: we begin to discover that there is no Other. Rooted in Buddhist wisdom, Quaker spiritual tradition, and decades of lived experience, Jerry, Sharon, and Parker reflect on the role of fear in keeping us apart, the necessity of community in doing this work, and the profound animating power of legacy. Of asking not just who we are now, but what kind of ancestors we are becoming. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

April 7, 202641 min

Wisdom for Work #31 - Navigating the Neutral Zone: Embracing Change & Transition

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 for a deep exploration of the Neutral Zone, drawing from William Bridges' classic framework on change and transition. Together, they reflect on their own experiences and share what it really means to metabolize transition at the organizational and human level. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

March 4, 20261 hr 3 min

#183 - The End of Suffering - with Sharon Salzberg & Jerry Colonna

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 wisdom but accessible to all, Jerry Colonna and Sharon Salzberg discuss what it means to relate differently to suffering, without denying its presence or being overtaken by it. Together, they reflect on the paradox of holding both pain and joy, and the importance of not confusing suffering with punishment or personal failure. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

December 18, 20259 min

Extras #27 - Reflection & Intention for the New Year - A Meditation Practice with Marty Janowitz

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 other parts of our experience that we so seldom make time for in our busy work lives. Find a quiet place to spend some time surfacing and working through whatever issue is present.

December 16, 20251 hr 11 min

#182 - What AI Therapy Misses: The Power of Human Presence - with Dr. Jud Brewer & Jerry Colonna

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 than challenge us, can subtly reinforce self-centered thinking and undermine real healing. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

November 25, 2025Episode 18151 min

#181 - Building The Company That 15-Year-Old You Needed - with Oliver Ravn & Jerry Colonna

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 journey through chronic illness, sharing raw stories of loneliness, stigma, and resilience. Together, Jerry Colonna and Oliver Achard Ravn examine the masks we wear, the wounds we carry, and the moments when compassion transforms isolation into community. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

October 23, 202553 min

#180 - Navigating Darkness, Perfectionism, and Purpose as an Entrepreneur - with Melissa Bernstein & Jerry Colonna

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 transformation—both in our work and in ourselves. In this episode, we welcome Melissa Bernstein, entrepreneur, creator, and co-founder of Melissa & Doug. With candor and warmth, Melissa shares insights from her latest book, The Heart of Entrepreneurship, reflecting on her lifelong dance between creativity and perfectionism, passion and patience, success and existential struggle. Together, Jerry and Melissa unpack what it means to persevere through the "rollercoaster" of building something meaningful, the importance of embracing imperfection, and the healing power of making our inner journeys visible. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

September 9, 20251 hr 1 min

#179 - The Work of Getting Free: Redemption, Gratitude & Hope - with Shaka Senghor & Jerry Colonna

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 instead forged in our minds—made of grief, shame, anger, and old stories. Shaka shares how his path of healing, reading, and a practice of gratitude helped him reimagine his life, and how his writing became both a discipline of self-emancipation. Shaka reflects on the obstacles he continues to face as a returning citizen, and the quiet oppressions that persist even after release. Yet, through gratitude, storytelling, and mentorship, he lights a way forward; not just for himself, but for all who seek to break the cycles of suffering and step more fully into their lives. Leave us a review on Apple Podcasts! Follow our step by step guides: How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

August 14, 202536 min

Wisdom for Work #30 - The Art of Influence: Building Trust & Connection at Work

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 it means to influence others, whether you're early in your career, leading cross-functional teams, or navigating challenges as an executive. Together, they explore how true influence is more akin to building bridges than issuing commands; it's about leveraging credibility, reliability, and, perhaps most crucially, vulnerability. From understanding the unwritten rules of your organization to building genuine relationships and balancing assertiveness with warmth, this conversation traces the inner work required for authentic influence. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup