The Reboot Podcast
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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#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...
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...
#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...
#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...
#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 da...
#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 bo...
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...
#178 - Discovering What Matters in a Distracted World - with Soren Gordhamer & Jerry Colonna
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 ongoing tension between ancient wisdom and contemporary life—discussing how our stories, our technology, and our hunger for achievement can draw us away from our deepest values and authentic selves. The pair asks what it means to live an...
Wisdom for Work #29 - Frameworks for Leading & Managing People
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 govern our relationships at work. The duo explores the power of establishing group norms, surfacing unspoken behaviors, and making the unconscious conscious. They highlight the transformative power of cultivating honesty, naming what's true, and leaning into crucial conversations...
#177 - What Does It Mean To End Well? - with Randy Goodman & Jerry Colonna
How do we navigate seismic shifts in our industries and our lives while striving to remain true to ourselves and those we care about? In this episode, Jerry sits down with Randy Goodman, recently retired Chairman and CEO of Sony Music Nashville, to reflect on a career arc that spans decades of change, challenge, and profound personal growth. Randy opens up about his time at the helm of Sony Music Nashville, leading through a rapidly transforming business landscape, the global pandemic, and the social upheaval of recent years. Together, Jerry and Randy explore the concept of "ending well," and what...
