PODCAST · business
The Reboot Podcast
by Reboot.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.
Episodes
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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...
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#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…
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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...
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#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...
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#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...
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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…
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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...
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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...
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#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....
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#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...
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#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...
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#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…
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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…
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#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,...
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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…
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#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...
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#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…
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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...
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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...
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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.…
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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…
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#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...
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#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…
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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...
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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…
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#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…
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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…
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#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...
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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…
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#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...
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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...
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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...
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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...
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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...
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#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...
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Extras #23 - Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear - with Noah Kagan
As a leader, how do you decide which inputs to listen to? What strategies do you use for personal growth and reflection? How do you create a work environment that supports and uplifts your team? In this episode, Reboot Co-founder Dan Putt engages in a candid conversation with Noah Kagan, the CEO…
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Wisdom for Work #19 - Strategic Delegation: Building Trust & Setting Clear Expectations
Delegation is one of the most essential skills to master as a leader. Done well, it's the fundamental behavior that impacts the culture, execution, and the bottom line. It creates inclusive leaders, flexible businesses, and the fostering of leaders in each seat in the organization. In this…
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#169 - Rupture + Repair = Resilience in Co-founder Relationships - with the Co-founders of Brood
In today's episode, Jerry Colonna engages in an insightful and deeply personal conversation with Emma, Gill, and Lizzy, the co-founders of Brood, a startup aiming to revolutionize modern family care. They share their experiences navigating the complexities of launching a startup amidst the...
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The Reunion Podcast - Episode 2 - Connecting with Ancestors & Embracing the Influence of Place
Welcome back to the Reunion Podcast, where we dive deep into the quest for belonging and explore the connection between ancestry, origin, and the desire for reunion. In this episode hosts Marshall Pollard and Jerry Colonna invite guests Grant and Darryl to share their experiences of seeking...
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The Reunion Podcast - Episode 1 - What If We All Belonged to Each Other? Ancestral Reunion, Belonging, and the Path to Healing
Welcome to The Reunion Podcast, where we dive deep into the stories that shape us, the struggles that push us, and the path to finding belonging in a world that often leaves us feeling lost. In this episode, Jerry Colonna and Marshall Pollard, along with guests Leticia and Erika, embark on a deep...
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The Reunion Podcast - Episode 0 - Reclaiming Our Stories: A Journey of Belonging and Reunion
Welcome to The Reunion Podcast, where we dive deep into stories of connection, reunion, and the power of radical self-inquiry. In this episode, Marshall and Jerry Colonna, your hosts, explore the importance of storytelling as a catalyst for belonging and understanding. They delve into the concept...
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Wisdom for Work #18 - Is Coaching Right for You? - with Dan Putt & Andy Crissinger
A common question we get asked at Reboot is: How do I know if coaching is right for me? In this episode, Reboot Coaches Dan Putt and Andy Crissinger delve into the world of coaching and its transformative impact on personal and professional growth. They shed light on what coaching entails,...
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#168 - The Healing Power of Tears: Building Empathy and Connection in a Numb World - with Benjamin Perry & Jerry Colonna
What is your relationship to crying? When was the last time you allowed yourself to weep openly? In this compelling episode of the Reboot Podcast, Jerry sits down with Benjamin Perry, minister and author of "Cry Baby: Why Our Tears Matter". Drawing from personal experiences and insightful...
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Wisdom for Work #17 - The Power of Retrospectives: Learning From the Past To Shape the Future
Retrospectives play a crucial role in building resilient teams. As organizations face constant change and uncertainty, having a regular ritual of collective learning provides stability and a sense of groundedness. It allows teams to adapt, innovate, and address challenges more effectively. In…
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Operator's Manual #8 - The Arc of Dysfunction: From Unhealthy Chaos to Healthy Creativity - with Ali Schultz & Jerry Colonna
What exactly is the Arc of Dysfunction, and why is it important for all organizations, especially startups? From the unhealthy and dysfunctional beginnings to the healthy and dysfunctional apex, Jerry and Ali explore the different stages of this arc and provide insights on how to navigate through...
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#167 - From Isolation to Openness: Engaging Fully with Real Life - with Sharon Salzberg & Jerry Colonna
When confronted with the realness of our lives, how we choose to respond matters. It's no easy feat to turn toward suffering when the world around us gets messy. However, when we open ourselves to love, we create a current of empathy that can lead us, and others, to community, connection, and...
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Wisdom for Work #16 - The Brightest Bulb Challenge: Moving From Individual Contributor to Team Leader
For individuals stepping more fully into leadership roles, the transition from individual contributor to team leader can bring about a myriad of feelings. What happens when you go from making something to building a team? In this Wisdom for Work, Andy Crissinger & Ray Foote describe the Brightest...
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#166 - We Can Choose to Ride the Roller Coaster of Entrepreneurship - with Jean Smart & Jerry Colonna
For leaders, navigating the roller coaster experience of entrepreneurship can be flat-out exhausting. The constant fluctuation of riding highs and surviving lows often leaves little time for reflection, much less appreciation for how far you've come. But what if there was a different way? What if...
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Operator's Manual #7 - When Should You Shut Down the Business? - with Ali Schultz & Jerry Colonna
How do you know when it's time to shut down the business? What does it take to come to this realization as the entrepreneur behind the wheel? In this Operator's Manual, Ali and Jerry dive into these questions, and touch on the perils of scaling and growth without a drive for profitability. Leave…
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Reboot Extra #22 - Scaling as a Technical Founder & CEO - with Evan Drumwright & Andy Crissinger
Being a technical founder poses particular challenges to scaling in your role as CEO. Scaling a company is challenging. Leading through that scale as your role as CEO is also constantly changing adds to the waves of change that a leader must move through on the arc of growth. In this podcast...
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ABOUT THIS 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.
HOSTED BY
Reboot.io
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Frequently Asked Questions
How many episodes does The Reboot Podcast have?
The Reboot Podcast currently has 259 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is The Reboot Podcast about?
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.
How often does The Reboot Podcast release new episodes?
The Reboot Podcast publishes regularly with 259 episodes available. Check the episode list for the typical release schedule.
Where can I listen to The Reboot Podcast?
You can listen to The Reboot Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts The Reboot Podcast?
The Reboot Podcast is created and hosted by Reboot.io.
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