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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

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 of AppSumo and author of the forthcoming book Million Dollar Weekend. Noah opens up about his path of personal and professional growth, sharing practical tools and hard-won wisdom for overcoming insecuri...

Jan 30, 202449 min

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 episode, Reboot Coaches Ali Schultz and Virginia Bauman dive into the world of delegation, highlighting the importance of clarity, trust, and accountability in the process. Virginia shares a valuable mental mo...

Jan 09, 202433 min

#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 pandemic, dealing with imposter syndrome, and the intense emotional and psychological challenges faced by startup founders. With Jerry's support, the triad explores their relationship to conflict and how to be...

Dec 08, 20231 hr 6 min

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 belonging in the face of division and systemic discrimination. Grant's story showcases the triumph and arrival he feels by breaking the curses of his forefathers, while living in a system designed to benefit ...

Nov 14, 202336 min

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 dive into the power of ancestral connections and the healing that comes from rediscovering our roots. Through a series of personal anecdotes and thought-provoking conversations, they navigate the comple...

Nov 14, 202331 min

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 of Reunion, emphasizing the need for diverse narratives that represent different experiences and foster empathy and compassion. Jerry and Marshall call for active listening, dialogue, and holding space ...

Nov 07, 202337 min

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, debunking common misconceptions and highlighting the importance of introspection and self-inquiry. Whether you are considering coaching for yourself or simply curious about the coaching process, this episode i...

Oct 25, 202313 min

#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 conversations, Jerry and Ben explore the impact of emotional numbness, the transformative power of shedding tears, and the profound connection that it fosters between individuals. From discussions on the suppre...

Oct 17, 202358 min

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 this episode, Andy walks through a simple framework called: What? So What? Now What? This framework is useful in both successes and failures. It helps us discover, collectively, a shared perspective of what...

Sep 26, 202315 min

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 them. Discover how understanding and acknowledging this arc can be liberating for leaders and teams, and how it can inform decision-making and company growth. Leave us a review on Apple Podcasts! Follow...

Sep 12, 202314 min

#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 healing. In this episode, our friend and teacher Sharon Salzberg returns to discuss her latest book, "Real Life: The Journey from Isolation to Openness and Freedom". Sharon reflects on how her COVID experie...

Aug 25, 202349 min

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 Bulb Challenge and discuss strategies to help leaders thrive as they transition from maker to leader. They make the case for conducting time and outcome audits and provide guidance for managing ener...

Aug 01, 202322 min

#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 you didn't have to ride the rollercoaster at all? In this episode, Jerry sits down with Jean Smart, founder and CEO of Penelope, a retirement savings platform exclusively for small business owners and t...

Jul 19, 202349 min

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 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.rebo...

Jul 06, 202310 min

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 conversation, Andy Crissinger sits down with Evan Drumwright, CEO of Dextrous Robotics. Evan reflects on his transition from academia to entrepreneurship and describes the unique challenges of scaling a comp...

Jun 20, 202332 min

Reboot Extra #21 - Climbing Out of the Pits of Despair - with Mollie West Duffy & Liz Fosslien

Content warning: This podcast contains conversations around self-harm and suicidal ideation. The pit of despair is a tough and tricky place. How can you find a way through when it feels like you're fumbling around in the dark? Mollie West Duffy and Liz Fosslien, authors of Big Feelings: How to Be Okay When Things Are Not Okay, return for another heartfelt conversation with Ali Schultz. In this episode, we define despair and describe how in all of its facets, it is not simply depression. Mollie s...

Jun 07, 202352 min

#165 - The Bones of Belonging - with Annahid Dashtgard & Jerry Colonna

In this episode of the Reboot Podcast, Jerry sits down with Annahid Dashtgard, a fellow author, activist, and champion for justice, equity, diversity, and inclusivity. The pair discuss Annahid's latest book, The Bones of Belonging: Finding Wholeness in a White World, which is a poignant collection of essays centered around Annahid's experiences searching for, and teaching about, belonging in our deeply divided world. Jerry and Annahid delve into the little, insidious, persistent ways we feel pre...

May 19, 202353 minEp. 165

#164 - How To Be a Stable Board Member - with Aileen Lee & Brad Feld

When markets are volatile and times are turbulent, being a VC can be a nerve-wracking experience. How should a seasoned board member handle themselves when anxieties are high? In this podcast conversation, Jerry sits down with Aileen Lee from Cowboy Ventures and Brad Feld from Foundry Group to discuss how to be an effective board member in stormy times. This conversation offers much to think about if you're a board member, new VC, or CEO. Leave us a review on Apple Podcasts! Follow our step by s...

May 05, 202358 min

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

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, Chris VandenBrink and Andy Crissinger talk about leaning into hard conversations so you can do so with s...

Apr 18, 202326 min

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

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 step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-compute...

Apr 04, 20239 min

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

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 adopting any of these practices can support you in becoming your best adult self. Leave us a review on Appl...

Mar 22, 202324 min

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

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 about the many facets of anger and how it has shown up in their own lives. The trio considers the po...

Mar 08, 202350 min

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

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 Koshin contemplate epigenetic trauma and the varying ways our personal suffering can be tangled by the ex...

Feb 28, 202345 minEp. 163

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

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 illustrate why the key to accountability is healthy channels of communication and cultures of trust. They ...

Feb 14, 202331 min

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

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 consider why adaptive leadership is so important for your organization's leaders, why it matters on an i...

Feb 01, 202318 min

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

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 to uncover and understand his own ancestors' history, and shares how returning to his family's past ...

Jan 17, 20231 hr 3 minEp. 162

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

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 sufficiency support you in feeling more grounded and centered. Leave us a review on Apple Podcasts! Follow o...

Dec 23, 20228 min

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

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 conversation with Liz Fosslien and Mollie West Duffy, authors of Big Feelings: How to Be Okay When Thi...

Dec 06, 202251 min

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

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 McAllister at Modern Executive Solutions. In their time together, the pair discuss the importance of clear...

Nov 23, 202240 min

Reboot Extra #16 - Mountain Meditation: Finding Your Center

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 finding your center and returning to stillness amidst turbulent times. May it be a grounding practice ...

Nov 10, 202211 min
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