Reboot.io

The Reboot Podcast

Business EN ↓ 255 episodes

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.

Author

Reboot.io

Category

Business

Podcast website

Reboot.io

Latest episode

Jun 9, 2026

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Episodes

Wisdom for Work #15 - Navigating Conflict & Difficult Conversations - with Chris VandenBrink & Andy Crissinger 18.04.2023

If you work with people, odds are good that hard conversations will be part of your work life. Whether it's firing an employee or dealing with tension in the executive team or trying to get along with a challenging personality at the office, managing people at any level, and in any scenario, makes difficult conversations inevitable and also essential to working well together. In this podcast, Chri...

Operator's Manual #6 - The Benefits of Bootstrapping - with Ali Schultz & Jerry Colonna 04.04.2023

Ever wonder what happened to building a good ol' profitable business? Maybe you wonder if there are benefits to bootstrapping in this world of high-growth, venture-backed companies with bloated valuations. In this bite-sized episode of Operator's Manual, Ali sits down with Jerry to discuss the very real benefits of bootstrapping a business. Leave us a review on Apple Podcasts! Follow our step by s...

Wisdom for Work #14: Micro-Practices for Leaders: Finding Ground & Setting Intention 22.03.2023

In this Wisdom for Work, Andy Crissinger and Chrystal Bell consider the importance of cultivating lasting practices that link to your values and how these ordinary rituals can support you. Chrystal describes the three key elements of practice: intention, attention, and repetition. The duo shares some simple micro-practices for grounding, centering, and setting intentions, and describes how adoptin...

Reboot Extra #20 - Anger As Messenger - with Mollie West Duffy, Chrystal Bell & Ali Schultz 08.03.2023

What is your relationship to anger? For many of us, anger is information. Often, it tells us when an important boundary has been crossed or alerts us when a value we hold dear is being threatened. The challenge of being an adult is finding healthy and generative ways to express our anger without hurting ourselves and others. In this episode, Mollie West Duffy returns to chat with Ali and Chrystal...

#163 - How To Bear Our Suffering - with Koshin Paley Ellison & Jerry Colonna 28.02.2023

In this episode of the Reboot Podcast, Jerry sits down with Koshin Paley Ellison, co-founder the New York Zen Center for Contemplative Care, to talk about his latest book, "Untangled". In his work as a contemplative caregiver, Koshin seeks to better understand the causes of suffering and works to nurture sources of strength such as resilience and compassion. In their time together, Jerry and Koshi...

Wisdom for Work #13: Accountability & Trust - with Virginia Bauman & Ali Schultz 14.02.2023

We often say trust is one person's assessment of another person's competence, sincerity, and reliability. Accountability is a related concept to trust, but it's also an inside job. Being accountable means being ready to show up for the work that's in front of us and be a contributor to the fulfillment of the goal of the whole. In this Wisdom for Work, Coaches Ali Schultz and Virginia Bauman illust...

Operator's Manual #5: Adaptive Leadership - with Ali Schultz & Jerry Colonna 01.02.2023

Adaptive leadership is the notion that a fixed leadership style isn't a quick fix or one-stop-shop for all your leadership needs. Adaptive leadership asks you to be keen enough to be with who is in front of you, in any situation, and be able to connect relationally and with what matters. That requires a different skillset than a fixed leadership style. In this Operator's Manual, Ali and Jerry cons...

#162 - Looking Back to Move Forward - with Lisa Sharon Harper & Jerry Colonna 17.01.2023

For our first fresh episode of the 2023 season, Jerry sits down with Lisa Sharon Harper, founder of Freedom Road, and author of the superb book, Fortune: How Race Broke My Family and The World and How to Repair it All. In this compelling conversation, Lisa tells the story of her ancestor, Fortune, as a way to illuminate the effects of race, racism, and Othering. Jerry describes the work he's done...

Reboot Extra #19 - Centering in Three Dimensions: A Practice 23.12.2022

Centering is a practice that brings us into present-moment awareness. Tuning into our breath and the sensations in our body opens up choice, clarity, and an enhanced ability to meet whatever we encounter. In this recording, Chrystal Bell shares a simple practice for feeling into the three planes of the human body - length, width, and depth. May reconnecting to your dignity, belonging, and sufficie...

Reboot Extra #18 - Fighting Compulsion: Detaching Our Worth from Our Work - with Mollie West Duffy & Liz Fosslien 06.12.2022

What fuels your relationship with work? When you're not working, what comes up for you? The compulsion to work can arise from various fears and drivers. Whether we are driven by perfectionism, tie our productivity to our worth, or use work to distract ourselves from other powerful demons such as shame, the spell of hustle culture can be hard to shake. In this podcast, we're sharing Ali's second co...

Reboot Extra #17 - Prep for Career Shifts and Job Changes - with Keith McAllister & Ali Schultz 23.11.2022

Whether we decide to leave our job, make a career move, or unexpectedly find ourselves without a job, the space between secure positions elicits a lot of things--unprocessed fresh feelings, needs, anxieties, and wondering about next steps. Often, that "next steps" part can feel like an overwhelming mountain. In this episode, Ali hosts a thoughtful conversation with executive recruiter Keith McAlli...

Reboot Extra #16 - Mountain Meditation: Finding Your Center 10.11.2022

Science tells us that the best time to meditate is often when it's not easy. Bringing mindfulness and perhaps even a pocket meditation for recentering to the situations when you are getting off-kilter, ungrounded, and upregulated are the moments that create lasting change. In this short clip, Reboot Coach and Facilitator Chrystal Bell leads a short meditation practice designed to support you in fi...

Reboot Extra #15 - Working With Chronic Illness - with Mollie West Duffy & Liz Fosslien 25.10.2022

Chronic illness and chronic pain are topics that can bring up a big mix of interconnected feelings -- uncertainty, burnout, anger, and even despair. They also challenge our perfectionism, make comparisons hard to stop, and can bring up thoughts of shame or even regrets. In this podcast, Ali kicks off the first in a series of conversations with Liz Fosslien and Mollie West Duffy authors of the book...

#161 - A Guidebook to Your Own Life - with Ian Sanders & Jerry Colonna 11.10.2022

In this podcast conversation, Jerry talks with Ian Sanders, author of "365 Ways to Have a Good Day", who found himself at the edge of rediscovery at the beginning of COVID lockdown. Fumbling and longing for ground, he dove into his past by paging through his old journals. Unearthing the stories of his life at that moment reminded him of who he was and what made him tick. His collection of entries...

Reboot Extra #14 - Women's Conversations: Your Personal Leadership Style - with Sally Helgesen & Ali Schultz 27.09.2022

Sally Helgesen is a women's leadership expert who has written many books over the past few decades on women and leadership (How Women Rise, The Female Advantage, The Web of Inclusion). In this episode, Sally and Ali Schultz explore the tendencies and habits that often contribute to women feeling stuck in their leadership roles. Sally describes how women leaders have a different perception, or way...

#143 - We're All Carrying Something - with Gino Zahnd & Jerry Colonna (re-release) 30.08.2022

As frequent listeners of the podcast can attest, a well-formed open, honest question can be a catalyst for radical self-inquiry and deep inner work. For Gino Zahnd, the founder of Cozy and Seabright, that question was, "What would I like the people that I work with to know about me that they don't know?." Gino, who lives with a rare genetic order called Fabry Disease, shares how one profound quest...

#160 - Learning From Regret - with Daniel Pink & Jerry Colonna 13.08.2022

What can we learn from regret? Regret gives us chance to see things from both sides. The experience we lived through, and the retrospective. Pausing to reflect on what was or has been allows us to see what we've learned from the vantage point of where we are now. As Dan Pink asserts in this podcast conversation and in his latest book, "The Power of Regret", regret is a clarifying emotion that is a...

Wisdom for Work #12 - Collective Planning as a Leadership Team - with Andy Crissinger & Jerry Colonna 26.07.2022

When considering collective planning as a team, what are the best practices leaders should adopt and what common pitfalls should they avoid? In this Wisdom for Work, Andy Crissinger and Jerry Colonna share why the actual planning process framework you choose is less important than the interpersonal dynamics among the team. The duo describes how a lack of trust can often undermine even the most tho...

#159 - The Power of Shared Leadership - with Andrew Alexseyenko & Jerry Colonna 12.07.2022

When faced with uncertain times and unavoidable challenges, how we show up matters. For some of us, a healthy reaction might be to withdraw and tend to the tender parts of ourselves that need support and care. For others, these crucible moments present an opportunity to lean into the work of our lives and give us the chance to truly discover the work we were born to do. In this episode, Jerry sits...

Wisdom for Work #11 - Career Transitions at Midlife - with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna 22.06.2022

In this conversation, Reboot Coaches Jim Marsden, Marty Janowitz, Ray Foote, and Jerry Colonna sit down to explore career transitions at midlife. Together, they describe their unique midlife experiences and share what was bubbling up for them at the time. They give insight into what helped them get to the other side and acknowledge the importance of honoring endings. Jim walks us through the arc o...

#158 - Show Up for Your Life - with Laurie Segall & Jerry Colonna 07.06.2022

Laurie Segall is an award-winning journalist, author, and the founder of Dot Dot Dot and D3 Network. In this episode, Laurie sits down with Jerry to chat about her tenure as CNN's Senior Tech correspondent and gives insight into her experience navigating the world of big media. The pair discuss what it means to "show up" for your life and why slowing down can often be so scary. Laurie reveals how...

Wisdom for Work #10 - Leader As Coach - with Andy Crissinger & Chris VandenBrink 25.05.2022

What are the benefits of adopting a coaching mindset in your leadership and life? In this podcast Wisdom for Work, Reboot Coaches Andy Crissinger and Chris VandenBrink break down the three fundamental components of coaching - listening, inquiry, and mirroring. The duo describes how incorporating a coach's mentality in your leadership toolkit can foster growth, learning, and creativity within your...

Reboot Extra #13 - Navigating High Conflict Personalities - with Megan Hunter & Ali Schultz 26.04.2022

Have you ever encountered a person in your life who you couldn't reason with the same way you could with so many others in your life? Are there some folks that make you act differently, or feel like you walk on eggshells around them? In this podcast, Ali sits down with Megan Hunter, a co-founder of The High Conflict Institute and expert on High Conflict Personalities (also known as HCPs). The pair...

#156 - Safety and Trust: The Crux of Adult Relationships - with Brad Feld & David Jilk 12.04.2022

At Reboot, we firmly believe that the act of leadership affords everyone the opportunity to grow into their most adult selves. Inquiring radically into our own psychologies and facing up to the truths behind our behavior allows us to lead and relate to others from a more informed place. In this podcast, Jerry sits down with Brad Feld and David Jilk, co-authors of "Entrepreneur's Weekly Nietzsche:...

Reboot Extra #12: Compassionate Abiding: A Guided Meditation for Anxious Times with Marty Janowitz 29.03.2022

What does it feel like to connect deeply with the groundlessness that arises during times of anxiety? In this short clip, Reboot Coach and Facilitator Marty Janowitz leads a short meditation practice in compassionate abiding. In this introductory practice, you'll focus on breathwork, sitting with uncertainty, and discovering what it means to reconnect with the cradle of our lovingkindness. Leave u...

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