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The Reboot Podcast

Reboot.ioreboot.io
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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Episodes

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 ...

Apr 07, 202641 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 diffe...

Mar 04, 20261 hr 3 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 p...

Dec 18, 20259 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 ...

Dec 16, 20251 hr 11 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. Togethe...

Nov 25, 202551 minEp. 181

#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, entre...

Oct 23, 202554 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 h...

Sep 09, 20251 hr 1 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, o...

Aug 14, 202537 min

#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 technolog...

Jul 10, 202555 min

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 ...

Jun 20, 202538 min

#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 s...

May 22, 202553 minEp. 177

#176 - Balancing Growth & Inner Purpose - with Christian Fenner, Mathias Tholey, Sebastian Ross, & Jerry Colonna

Jerry Colonna sits down with Christian Fenner and Mathias Tholey, co-founders of Nucao, alongside Sebastian Ross, the driving force behind the School of Founders at IESE Business School in Barcelona. Christian and Mathias share their entrepreneurial journey from a crisis of purpose while working in traditional careers to founding a sustainable chocolate company deeply rooted in addressing environmental and social challenges. They dive into the trials of initial successes, the allure of scaling r...

Apr 17, 20251 hr 17 min

Wisdom for Work #28 - Working With Intuition

In this episode, Miriam Meima and Ali Schultz explore one of our favorite topics: intuition. Intuition is the ability to understand something immediately, without conscious reasoning. They discuss our hunches about how refining our intuition can benefit us at work and what that might entail. They also provide a few exercises to help you engage with your own intuition, allowing you to incorporate it more into your life and work. Leave us a review on Apple Podcasts! Follow our step by step guides:...

Mar 03, 202535 min

Wisdom for Work #27 - Parsing Emotional Data

How do we connect with our deeper emotional landscape? Miriam Meima joins Ali to explore the power of emotional intelligence and what our feelings can teach us about ourselves. Together, they unpack the unexplored corners of human experience and share the practical "7 Steps to Sanity" framework—a tool for riding emotional waves, finding clarity, and moving forward with purpose. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reb...

Jan 23, 202545 min

Wisdom for Work #26 - Staying Grounded Throughout Your Work Day

Some days can get away from you before you sit down at your desk, while other days can be a slog. As our days pull us along or come at us, we ride the waves of our own regulation. Being able to find our center when we get knocked off course can help us navigate the day with more ease and grace. In this podcast episode, Miriam Meima and Ali talk about ways to set yourself up for the day--no matter what happens. They inquire about and surface ways to help you stay present and anchored in a full-bo...

Dec 03, 202442 min

Extras #26 - Moving From Fragility to Robustness - with Kelly Wendorf & Ali Schultz

Where are your delicate and vulnerable spots that, when touched, cause a defensive reaction? In this thought-provoking episode, Ali explores the concept of fragility with Kelly Wendorf, founder of Equus and author of "Flying Lead Change." Kelly, a horse-wise woman and insightful author, unpacks how our most vulnerable spots trigger defensive reactions in both personal and professional settings. She illuminates the origins of our fragile responses, examining how shame triggers can impact our lead...

Oct 29, 202449 min

#175 - Beyond the Self: Embracing Interconnectedness - with Luis Duarte & Jerry Colonna

Join Jerry Colonna and Luis Duarte for a thought-provoking conversation on the power of interconnectedness and the importance of finding purpose in our lives. Luis, a passionate entrepreneur and Co-Founder of Amoofy, shares his inspiring journey of building a company centered around human connection and the transformative power of storytelling. Discover how Luis's personal experiences, shaped by his family's history and his own challenges, led him to create a platform that fosters deeper connect...

Sep 24, 20241 hr 4 minEp. 175

#174 - Leading With Love & Intention - with Dr. Nicole Marie Ortiz & Jerry Colonna

In a world where intentional action seems like a rarity, Nicole Ortiz, Director of Leadership and Belonging at the Denver Zoo, stands out with her deliberate approach to work and life. In this powerful episode, Jerry Colonna sits down with Nicole to explore the concept of intentionality, exploring how it shapes her approach to leadership and her work in diversity, equity, and inclusion. Nicole shares how her role at the Denver Zoo has evolved and highlights why welcoming resistance, holding spac...

Aug 27, 202448 minEp. 174

Extras #25 - The Power of Horses for Coach Development - with Kelly Wendorf & Liz Stewart

In this Reboot Extras episode, Ali sits down with Liz Stewart and Kelly Wendorf to talk about Reboot's upcoming Coach Retreat, the value of coach supervision, and how working with horses can support coaches in their growth towards maturity and mastery. Liz is a coach supervisor, and Kelly is the founder of EQUUS - an equine facilitated learning campus situated in Santa Fe, New Mexico. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: ...

Aug 15, 202427 min

Wisdom for Work #25 - The Art of Generative Listening

In this episode, Miriam Meima returns to discuss the art of generative listening with Ali Schultz. They explore the significance of optimizing interactions, the pitfalls of selective listening, and the importance of cultivating open communication. Miriam unpacks the levels of listening, emphasizing the transformative power of level five listening. Together, Miriam and Ali unravel the complexities of communication, providing practical insights for navigating high-pressure situations and cultivati...

Jul 30, 202445 min

#173 - Celebrating Difference in Your Company - with Rob Castaneda & Jerry Colonna

In this episode of The Reboot Podcast, Jerry sits down with Rob Castaneda, the founder and CEO of Service Rocket. Together, they unpack the importance of empathy, fostering a sense of belonging, and celebrating the rich tapestry of experiences that employees bring to the table. Rob shares powerful personal stories illuminating the contrasting effects of inclusion and exclusion, highlighting how embracing cultural heritage can strengthen not just individuals, but entire organizations. Discover ho...

Jul 16, 202456 min

Wisdom for Work #24 - Unlocking Imposter Syndrome

In this episode, Ali Schultz reunites with coach Miriam Meima for a heartfelt conversation about imposter syndrome. They move beyond simply acknowledging the phenomenon, and instead, share practical strategies for managing it effectively. Miriam offers a fresh perspective, framing imposter syndrome as the gap between our perceived capability and perceived expectations, and provides advice for making those situations feel less overwhelming. The duo emphasizes the power of choice, and how when we ...

Jun 18, 202439 min

#172 - Finding Closure After Shutting Down the Business - with João Barros & Jerry Colonna

There's more to leadership than building the next billion-dollar unicorn. Our guest, João Barros, has walked a fascinating path – from professor to CEO and back again. In this candid conversation with Jerry, João reflects on his entrepreneurial journey, making the gut-wrenching decision to close down his business, and how attending a Reboot Bootcamp empowered him during this difficult time. Join us as we challenge conventional success paradigms, honor diverse paths to leadership, and highlight w...

Jun 04, 202457 min

Wisdom for Work #23 - Cultivating Conditions of Courage

How can leaders create a safe space for honest conversations, even when those truths challenge the status quo? In this episode of Wisdom for Work, Reboot Coaches Ali Schultz and Virginia Bauman unpack the concept of "conditions of courage," exploring how fostering psychological safety within teams goes hand-in-hand with individual leaders cultivating self-awareness about the conditions that empower them to be honest. Through personal stories and insightful discussion, they unpack the power of se...

May 14, 202427 min

#171 - The Great Midlife Edit - with Chip Conley & Jerry Colonna

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. Together, they explore the transformational journey of embracing midlife as a time of growth and wisdom. Chip shares his personal tale of crisis and renewal, emphasizing the fear and cultural pressures surrounding aging. They ponder the role of an elder and the importance of embracing uncertainty, impermanence, and transitio...

Apr 30, 202450 min

Wisdom for Work #22 - Owning Your Strengths

We all have that nagging voice in our head, the inner critic, that loves to point out our flaws. But what if there was a way to silence that bully and amplify a different voice, your inner advocate? In this episode, Ali chats with fellow coach Miriam Meima about taming the inner critic and unleashing your inner champion. This episode is for anyone who has felt like they're not good enough, replays past conversations in their head, or struggles to see their unique strengths. Leave us a review on ...

Apr 19, 202444 min

Extras #24 - Building High-Performing Teams Through Coaching - with Steph Yiu

In this Podcast Extra, Andy Crissinger delves into the world of coaching and its transformative impact on corporate culture with guest Steph Yiu, Chief Customer Officer at WordPress VIP and leader at Automattic. They explore the extensive Reboot program at Automattic, which focuses on trust, open feedback, and building a supportive environment for personal and professional growth. Steph shares her journey of incorporating coaching tools into her leadership role, and they discuss how these tools ...

Mar 30, 202435 min

Wisdom for Work #21 - Engaging Your Team to Bring Out Their Best

How do you engage your team to bring out their best? In this Wisdom for Work, Reboot Coaches Andy Crissinger, Jen Cody, Jim Marsden, and Chris VandenBrink gather to explore the critical importance of clarity, communication, and understanding within a team dynamic. The group highlights the significance of understanding team members' working preferences, motivations, and values to build relationships, set expectations, and create clarity within the team. Join the conversation as they explore pract...

Mar 15, 202430 min

Wisdom for Work #20 - The Art of Firing Well

If you're a leader, few things can ruin your day more than needing to fire someone. It's just plain hard to do, even when you know it's the right decision. In this insightful discussion, Ali and fellow coach Heather Jassy share advice for effectively and compassionately handling the challenging task of letting someone go from their job. Heather shares her script for handling the firing process with clarity and empathy, acknowledging the discomfort and awkwardness of such conversations while stri...

Feb 27, 202435 min

#170 - The Brave Leader's Path: Fostering Inclusivity & Courageous Decision-Making - with David McQueen & Jerry Colonna

What does it mean to lead bravely? In this powerful episode, Jerry Colonna explores the essential elements of ethical leadership with David McQueen, author of "The Brave Leader." David sheds light on the difference between ethical and moral decision-making, emphasizing the courage and resilience needed to navigate the gray areas while staying true to core values. He emphasizes the importance of not just fostering diversity, but building true inclusion, where every voice is heard, valued, and emp...

Feb 13, 202454 min
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