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PODCAST

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.

business careers

All Episodes

35:50

Extras #24 - Building High-Performing Teams Through...

The Reboot Podcast ·

2024/03/30

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 have

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31:14

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

The Reboot Podcast ·

2024/03/15

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 practical

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36:36

Wisdom for Work #20 - The Art of Firing Well

The Reboot Podcast ·

2024/02/27

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

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54:52

#170 - The Brave Leader's Path: Fostering Inclusivity...

The Reboot Podcast ·

2024/02/13

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

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51:07

Extras #23 - Unleashing Potential: Insights on...

The Reboot Podcast ·

2024/01/30

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

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34:16

Wisdom for Work #19 - Strategic Delegation: Building...

The Reboot Podcast ·

2024/01/09

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 model

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01:07:16

#169 - Rupture + Repair = Resilience in Co-founder...

The Reboot Podcast ·

2023/12/08

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 best

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36:25

The Reunion Podcast - Episode 2 - Connecting with...

The Reboot Podcast ·

2023/11/14

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 him

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31:25

The Reunion Podcast - Episode 1 - What If We All...

The Reboot Podcast ·

2023/11/14

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

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37:00

The Reunion Podcast - Episode 0 - Reclaiming Our...

The Reboot Podcast ·

2023/11/07

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 for

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13:41

Wisdom for Work #18 - Is Coaching Right for You? -...

The Reboot Podcast ·

2023/10/25

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 is

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01:00:13

#168 - The Healing Power of Tears: Building Empathy...

The Reboot Podcast ·

2023/10/17

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

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16:35

Wisdom for Work #17 - The Power of Retrospectives:...

The Reboot Podcast ·

2023/09/26

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

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15:18

Operator’s Manual #8 - The Arc of Dysfunction: From...

The Reboot Podcast ·

2023/09/12

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 our

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51:39

#167 - From Isolation to Openness: Engaging Fully...

The Reboot Podcast ·

2023/08/25

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 experience

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24:13

Wisdom for Work #16 - The Brightest Bulb Challenge:...

The Reboot Podcast ·

2023/08/01

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 energy and

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49:46

#166 - We Can Choose to Ride the Roller Coaster of...

The Reboot Podcast ·

2023/07/19

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 their

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11:51

Operator’s Manual #7 - When Should You Shut Down the...

The Reboot Podcast ·

2023/07/06

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: - How To: Leave a Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay

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33:45

Reboot Extra #22 - Scaling as a Technical Founder &...

The Reboot Podcast ·

2023/06/20

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 company

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54:34

Reboot Extra #21 - Climbing Out of the Pits of...

The Reboot Podcast ·

2023/06/07

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

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