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 Working #1: Ladder of Inference - with Andy Crissinger 23.04.2020

Bringing what's unexamined into the light of what's examined can help us communicate and collaborate more effectively, especially during times of difficulty. In this short clip, Andy Crissinger, Reboot's Director of Coaching, shares the "Ladder of Inference" tool used in Reboot's coaching and leadership development trainings. Leave us a review on Apple Podcasts! Follow our step by step guides: - H...

#122 - Hardwired for Joy - with Jerry Colonna & Ingrid Fetell Lee 16.04.2020

When the disquiet and unease of turbulent times weigh heavy on our hearts, can opening ourselves up to joy provide respite from the loads we carry? Ingrid Fetell Lee, designer and author of ​Joyful: The Surprising Power of Ordinary Things to Create Extraordinary Happiness, joins Jerry for an exploration of how the experience of joy can serve as a balm in times of crisis. In this episode, Jerry and...

#121 Belonging Together - with Chris VandenBrink, Dan Putt, Andy Crissinger & Carl Baccellieri 03.04.2020

Peer support is incredibly valuable. Folks at all levels within your company need support, especially now. In these times it's more important than ever to stay connected, which can be a challenge when physical isolation is a requirement. In this special podcast release, Reboot coaches Chris VandenBrink, Dan Putt, Andy Crissinger & Carl Baccellieri share what we as an organization have learned abou...

Reboot Extra #7: Women's Conversations - I Am Enough: Vulnerability, Imposter Syndrome, and Confidence 13.03.2020

When it comes to confidence, feeling A-Ok with showing vulnerability, and trying to avoid the sneaky snares of Imposter Syndrome, we often feel at odds, torn between the parts of us that say, "Who do you think you are?" and the parts of us who know who we are. Self-doubt and inadequacy can creep in and color the most assured parts of us at times. But, what's really at play here? We know it's an in...

#120 - Breaking the Cycle - with Jennifer Goldman-Wetzler & Jerry Colonna 27.02.2020

In this episode, Jerry welcomes fellow author Jennifer Goldman-Wetzler to the podcast to explore her latest book: Optimal Outcomes: Free Yourself from Conflict at Work, at Home, and In Life. In this dialogue, Jennifer shares how tensions in her own life propelled the desire to discern the ways in which emotions like grief, anger, fear, and sadness manifest in times of conflict. Jerry and Jennifer...

#119 - Investing in Trust (re-release) - with Fred Wilson & Jerry Colonna 14.02.2020

In over 19 years of friendship and partnership in the startup world, Jerry and Fred have seen just about everything. In this conversation, they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey. Leave us a review on i...

#118 - The Business Case for Love - with Steve Farber & Jerry Colonna 30.01.2020

"Love isn't merely some second-hand emotion; love is the fuel that powers great organizations." - Jerry Colonna In this episode of the Reboot Podcast, Jerry sits down with Steve Farber, author of Love Is Just Damn Good Business, for a conversation on leadership and the value of love in the workplace. As Steve reflects on the transformational power of love, Jerry unpacks the ways in which it cultiv...

Reboot Extra #6: Women's Conversations - Family Time: Going Back to Work, Mom Guilt & Other Fertile Matters 17.01.2020

For our first fresh conversation of 2020 we're releasing the next installment in our Women's Conversation series, a collaborative discussion sparked by our coaches who identity as women, on what women face in work and in life. In today's episode, Reboot co-founder Ali Schultz is joined by fellow executive coaches Heather Jassy and Ann Mehl for a dialogue centered around motherhood and fertility, a...

#117 - Reclaiming The Shadow - with Tracy Lawrence (re-release) 03.01.2020

Tracy Lawrence, Co-founder and CEO of Chewse, joins Jerry talk about authenticity, leading from the heart and on the power of embracing the lost and disowned parts of ourselves, the parts in her shadow. For Tracy, it's not only about being there for the little girl who was bullied in middle school, but also about owning her very own inner bully. Reclaiming that part of herself will not only impact...

#116 - When Old Maps No Longer Work - with Dylan Bowman & Jerry Colonna 05.12.2019

In this episode of the Reboot Podcast, we welcome professional ultramarathon runner Dylan Bowman. After an explosive season of personal successes on the race circuit, Dylan shares how an abrupt series of injuries and unexpected setbacks rattled his perceptions of control and precipitated questions about identity and self-worth. Conversing with Jerry, Dylan expands on how the obstacles he's faced h...

Reboot Extra #5: Women's Conversations: Making Space for Your Own Truth 22.11.2019

This Reboot Extra marks the first of a Women's Conversation series, a collaborative discussion with Reboot's coaches who identify as women, on the realities of women in work and life. We'll go broad and deep on a bosom-full of topics that can weigh on a woman's heart; finding solidarity as we weave insight from a range of well-hewn threads of wisdom - our own experience as women in the workplace,...

#115 - This Could Be Our Future - with Yancey Strickler & Jerry Colonna 31.10.2019

On this episode of the Reboot Podcast Jerry sits down with Yancey Strickler (Co-founder and former CEO of Kickstarter) to explore his recently released book, "This Could Be Our Future: A Manifesto for a More Generous World," which lays out a vision for building a society that looks beyond money and toward maximizing the values that make life worth living. During this conversation, Yancey and Jerry...

#114 - The Shoulds of the Past & the Anxieties of the Future - with Shizu Okusa & Jerry Colonna 15.10.2019

Along the entrepreneurial journey there comes a time and place for all leaders where we lift our heads from the fog of busyness to find ourselves on an unknown path. Knowing where we are isn't exactly where we intended to be, we look to the past for clues to how we've landed in this spot. For many, this is the integral moment in which we come to realize that our internal and external selves have f...

#113 - Invest in Being Yourself (re-release) - with Bryce Roberts & Chris Marks 26.09.2019

VC's Bryce Roberts of OATV and Indie.vc, and Chris Marks of Blue Note Ventures both found the standard issue of the VC world was not a fit for them. They both sought out to set a new path, one that aligned with who they are and what they value. In a conversation with Jerry, and each other, they explore the challenges on their journey, and the potential opportunities they have to better connect wit...

#112 - Stay and Face It - with Fleet Maull & Jerry Colonna 14.09.2019

On this episode of the Reboot Podcast, Jerry is joined by Fleet Maull, a fellow coach, social entrepreneur, and author of the recently released book, ​"Radical Responsibility". ​ In this conversation, Fleet shares how his experience in the US prison system served as the impetus for the formation, development, and personal application of his radical responsibility philosophy. As Fleet characterizes...

#111 - Standing in the Gap - with Amy Nelson & Jerry Colonna 29.08.2019

Although the challenges women leaders face today have been well documented and highly publicized and most of us recognize that women are often forced to tackle unique and disproportionate challenges from their male counterparts, it can be hard to fully empathize with the biases with which we ourselves may not be called to face. On this week's podcast, you'll meet one female founder who generously...

#110 - The Mother of Invention - with Jules Pieri & Jerry Colonna 16.08.2019

A maker: people or hobbyists who pursue the creation of a business around an individual product. On this episode of the Reboot Podcast we welcome Jules Pieri, (Co-founder and CEO of The Grommet) back to the show for the third time. In this dialogue with Jerry, Jules describes the maker space and shares a few stories about entrepreneurs from her new book How We Make Stuff Now: Turn Ideas into Produ...

#109 - With Great Power Comes Great Responsibility - with Dan Harris & Jerry Colonna 25.07.2019

On this episode of the Reboot Podcast, we're sharing a special conversation between Jerry Colonna and Dan Harris (ABC News, 10% Happier) that was hosted and recorded by the Rubin Museum of Art earlier this month. In this dialogue, Dan and Jerry explore the importance of radical self-inquiry in leadership and life. Jerry conveys the ways in which the sub-routines of our youth influence the way we s...

#108 - Leading Shoulder to Shoulder - with Sara Hicks & Mathias Meyer 12.07.2019

In this modern age, the ability to connect across continents and timezones is pivotal for a globally distributed team. While email, video calls, and chatting services provide the means to instantly connect, how successfully do we ​truly​ manage to communicate within all these channels? For Sara Hicks, CEO and Co-founder of Reaction Commerce, and recently appointed CTO Mathias Meyer, finding congru...

#107 - Reboot: Leadership & the Art of Growing Up - with Jerry Colonna 18.06.2019

For this special episode, we're celebrating the release of podcast host and Reboot Co-founder Jerry Colonna's new book, "Reboot: Leadership and the Art of Growing Up." ( www.rebootbyjerry.com ). In this conversation, Jerry delves into why he wrote the book, opening up about how his life-long practice of journaling influenced the book's format, and what he hopes those who've read the book will gain...

#106 - Chasing Purpose - with Jeff Orlowski & Jerry Colonna 06.06.2019

Jerry is joined by cinematographer and filmmaker Jeff Orlowski, best known for his critically acclaimed documentary films - Chasing Coral & Chasing Ice. The Emmy Award-winning filmmaker recently received the United Nations' highest environmental honor, the Champions of the Earth award, for his work on spreading powerful environmental messages to a global audience. Believing that film remains one o...

#105 - Reboot Your Definition of Success - with Alex Rethore & Jerry Colonna 23.05.2019

A self-described planner, Alex Rethore, startup executive and founder of The Brecken Group, a consultancy that supports teams scale by driving revenue and improving operational effectiveness, comes to Jerry bridled with anxiety, yearning for clarity and a roadmap to her future. At the time of this conversation, Alex had reached out to Jerry for guidance and support through a particularly cloudy tr...

#104 - The Next Chapter - with David Ryan & Jerry Colonna 10.05.2019

For all leaders, periods of transitional change usher the impetus for self-inquiry. Whether unforeseen or even expected, transitions provide an opportunity to consider where we are now and where we'd like to be in the future. As our center of gravity shifts, we're given space to ponder what's on the horizon, oftentimes considering how we will find our way forward when we're still so strongly tied...

#103 - What Kind of Company Do You Want to Work For? - with Chris Savage & Brendan Schwartz 27.04.2019

For entrepreneurs today, advice on the 'best practices' for building a fruitful company abound - prescriptions for raising capital, increasing revenue, and hiring the correct team are often just a click (or the turn of a page) away. In periods of expansion and evolution, founders are tasked with making and implementing pivotal decisions necessary for propelling growth. During these times, it's not...

#102 – To Actually Live Your Life – with Khe Hy & Jerry Colonna 04.04.2019

In this episode, we welcome back Khe Hy, founder of Rad Reads, to the Reboot Podcast for a second time. In his first appearance, Jerry worked with Khe to shed light on the ways in which his unrealized fears surrounding death had contributed to a lack of stillness and presence in his life. Eighteen months after their initial discussion, Khe reconnects with Jerry to explore new questions surrounding...

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