The Reboot Podcast

Hosted by Reboot.io

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257

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Aug 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

September 8, 202646 min

Reboot Extras #28 - Beyond Mentoring: Exploring the Essential Role of Supervision in Coaching

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 it's vital, and how it differs from mentoring. They highlight some of the unseen burdens coaches carry, the importance of having a reflective practice, and the sacredness of creating genuine, ethical relationships with clients. They remind us that supervision isn't just about staying current or professional; it's about self-knowledge, healing, and love. 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 18, 2026Episode 18645 min

#186 - Rewiring Our Relationship With Money - with Michelle Masters & Jerry Colonna

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 shares stories from her work with clients, including billionaires who still feel anxiety, and explains why our deepest money issues can't be solved by intellect alone. Together, they illuminate how lasting change comes from tending to the subconscious and somatic origins of our beliefs, allowing us to transform money from a source of fear to a blessing. 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

July 16, 202652 min

Wisdom for Work #32 - Beyond the Review: Rethinking How We Talk About Performance at Work

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 performance management is often so challenging and how organizations can move toward deeper clarity, honesty, and engagement. Together, Jerry and Angela explore the essential role of transparency, skilled managers, and genuine conversations in building cultures where people thrive. She reflects on how workplace dynamics are evolving in the wake of the pandemic and amid the rise of AI, challenging leaders and employees alike to consider what constitutes a truly meaningful and reciprocal workplace contract. 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

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