The Reboot Podcast

By Reboot.io

What's 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.

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The Reboot Podcast episodes:

04.19.2024
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...
03.30.2024
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...
03.15.2024
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...
02.27.2024
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...
02.13.2024
#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...
01.30.2024
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...
01.09.2024
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...
12.08.2023
#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...
11.14.2023
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...
11.14.2023
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...
11.07.2023
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...
10.25.2023
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...
10.17.2023
#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...
09.26.2023
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...
09.12.2023
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...
08.25.2023
#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...
08.01.2023
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,...
07.19.2023
#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...
07.06.2023
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...
06.20.2023
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...
06.07.2023
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...
05.19.2023
#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...
05.05.2023
#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...
04.18.2023
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...
04.04.2023
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...
03.22.2023
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,...
03.08.2023
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...
02.28.2023
#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...
02.14.2023
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...
02.01.2023
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...
01.17.2023
#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...
12.23.2022
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...
12.06.2022
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...
11.23.2022
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...
11.10.2022
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...
10.25.2022
Reboot Extra #15 - Working With Chronic Illness - with Mollie West Duffy & Liz Fosslien
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...
10.11.2022
#161 - A Guidebook to Your Own Life - with Ian Sanders & Jerry Colonna
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...
09.27.2022
Reboot Extra #14 - Women’s Conversations: Your Personal Leadership Style - with Sally Helgesen & Ali Schultz
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...
08.30.2022
#143 - We’re All Carrying Something - with Gino Zahnd & Jerry Colonna (re-release)
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...
08.13.2022
#160 - Learning From Regret - with Daniel Pink & Jerry Colonna
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...
07.26.2022
Wisdom for Work #12 - Collective Planning as a Leadership Team - with Andy Crissinger & Jerry Colonna
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...
07.12.2022
#159 - The Power of Shared Leadership - with Andrew Alexseyenko & Jerry Colonna
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...
06.22.2022
Wisdom for Work #11 - Career Transitions at Midlife - with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna
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....
06.07.2022
#158 - Show Up for Your Life - with Laurie Segall & Jerry Colonna
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...
05.25.2022
Wisdom for Work #10 - Leader As Coach - with Andy Crissinger & Chris VandenBrink
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...
05.10.2022
#157 - When Are You Done? - with Chris Remus & Jerry Colonna
In this podcast, Jerry sits down with Chris Remus, Founder of Chainflow, to explore an enormously complex and personal question, “What does it mean to be done?” What unfolds is a thought-provoking conversation around our relationship to work, and why...
04.26.2022
Reboot Extra #13 - Navigating High Conflict Personalities - with Megan Hunter & Ali Schultz
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...
04.12.2022
#156 - Safety and Trust: The Crux of Adult Relationships - with Brad Feld & David Jilk
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...
03.29.2022
Reboot Extra #12: Compassionate Abiding: A Guided Meditation for Anxious Times with Marty Janowitz
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...
03.17.2022
Reboot Extra #11: Women's Conversations - Finding Joy & Creative Habits - with Rachel Ryle & Ali Schultz
In this Podcast Extra, Reboot Co-founder Ali Schultz sits down with Rachel Ryle, an award-winning animator, illustrator, and storyteller. Rachel describes how tending to her energy and taking ownership of her mental health has brought more purpose and fulfillment to...

What's The Reboot Podcast about?

Download our free app to listen on your phone

The Reboot Podcast episodes:

Wisdom for Work #22 - Owning Your Strengths

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

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

Wisdom for Work #20 - The Art of Firing Well

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

Extras #23 - Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear - with Noah Kagan

Wisdom for Work #19 - Strategic Delegation: Building Trust & Setting Clear Expectations

#169 - Rupture + Repair = Resilience in Co-founder Relationships - with the Co-founders of Brood

The Reunion Podcast - Episode 2 - Connecting with Ancestors & Embracing the Influence of Place

The Reunion Podcast - Episode 1 - What If We All Belonged to Each Other? Ancestral Reunion, Belonging, and the Path to Healing

The Reunion Podcast - Episode 0 - Reclaiming Our Stories: A Journey of Belonging and Reunion

Wisdom for Work #18 - Is Coaching Right for You? - with Dan Putt & Andy Crissinger

#168 - The Healing Power of Tears: Building Empathy and Connection in a Numb World - with Benjamin Perry & Jerry Colonna

Wisdom for Work #17 - The Power of Retrospectives: Learning From the Past To Shape the Future

Operator’s Manual #8 - The Arc of Dysfunction: From Unhealthy Chaos to Healthy Creativity - with Ali Schultz & Jerry Colonna

#167 - From Isolation to Openness: Engaging Fully with Real Life - with Sharon Salzberg & Jerry Colonna

Wisdom for Work #16 - The Brightest Bulb Challenge: Moving From Individual Contributor to Team Leader

#166 - We Can Choose to Ride the Roller Coaster of Entrepreneurship - with Jean Smart & Jerry Colonna

Operator’s Manual #7 - When Should You Shut Down the Business? - with Ali Schultz & Jerry Colonna

Reboot Extra #22 - Scaling as a Technical Founder & CEO - with Evan Drumwright & Andy Crissinger

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Reboot Extra #16 - Mountain Meditation: Finding Your Center

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

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

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

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

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

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

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

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

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

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

#157 - When Are You Done? - with Chris Remus & Jerry Colonna

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

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

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

Reboot Extra #11: Women's Conversations - Finding Joy & Creative Habits - with Rachel Ryle & Ali Schultz