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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

12:53

Operator's Manual #1: What IS the Job of the CEO? -...

The Reboot Podcast ·

2021/11/18

We wanted to bring you a new-ish kind of conversation to our podcast channel - but not new to the halls of Reboot. This one is for the operators, where we talk about the practical-tactical challenges that come from scaling an organization and growing in your leadership. In these conversations, Ali Schultz sits down with Jerry Colonna and gets him to wax-practical the common topics we see leaders face. In this episode of our Operators Manual series, Ali and Jerry discuss: What is the job of the CEO

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57:10

#152 - Facts, Not Flaws - with Philip Deng & Jerry...

The Reboot Podcast ·

2021/11/04

After a decade of working in nonprofits, Philip Deng has decided to build something of his own. In this conversation, Philip sits down with Jerry to chat about his company Grantable, which helps individuals and organizations make grant writing more efficient. Philip, who identifies as Asian American, opens up about the loneliness he’s faced as a leader and CEO. He reflects on how the events of his childhood, specifically his parents divorce, left him with complicated feelings about his self-worth

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49:23

#151 - The Heartbreak of Every Day - with Nitin...

The Reboot Podcast ·

2021/10/13

The Reboot Podcast has hosted a wide variety of conversations around the complexity and diversity of the co-founder experience, such as the importance of communication, the power of mindfulness in partnerships, and shared our advice for navigating co-founder conflict. Co-founders looking to meet the day-to-day challenges of running a business must commit to consistent work in aligning their vision and purpose for the organization, but what happens when an unforeseen tragedy throws all your

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01:03:12

#150 - Behind the Mask - with Ashanti Branch & Jerry...

The Reboot Podcast ·

2021/09/28

In this 150th episode, we are privileged to share Jerry’s conversation with Ashanti Branch, Founder and Executive Director of The Ever Forward Club, whose mission is to transform the lives of underserved youth by providing safe opportunities for academic, personal, family, and community development. Ashanti reflects on his experiences as a young black man, the pressure he felt to conceal his true emotions from his peers, the ways in which men are conditioned to neglect their feelings, and why his

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22:45

Reboot Extra #9: 360° Reviews: Feedback as a Powerful...

The Reboot Podcast ·

2021/08/24

In order to become the leaders we were born to be, we must first be willing to radically inquire within. By cultivating a deep growth mindset, we’re able to mature and develop not only as leaders but as humans. Getting curious about our blind spots in leadership and seeing clearly our strengths and weaknesses as well as understanding how we are perceived is the basis for any leadership development plan. We cannot grow if we don’t understand the work we have to do. In this episode, Andy Crissinger

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51:27

#149 - Tending the Garden of Democracy - with Amy...

The Reboot Podcast ·

2021/08/11

Amy McGrath is a retired US Marine Corps Lieutenant Colonel, the founder of Honor Bound - a 501(c)(4) nonpartisan organization committed to leadership development for women with a service background and encouraging those women to run for elected office, and a proud Kentuckian to boot. Amy sits down with Jerry to chat about her time in the military, how it shaped her views on service and honor, and why she felt compelled to run for the US Senate in the 2020 election. Amy discusses her new book,

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54:23

#148 - When Your Company Grows You - with David...

The Reboot Podcast ·

2021/07/27

On this episode of the Reboot Podcast, Jerry hosts a conversation with David Hieatt, co-founder of Hiut Denim Company. In this exchange, David recounts how the sale of his first company left him feeling listless and ungrounded. He shares how he regained his sense of purpose after founding Hiut, a company that revived the denim industry in the small town of Cardigan, Wales. David describes the difficult process of temporarily closing the factory due to COVID-19 and how these past few months have

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55:54

#147 - Power, Progress, and Generative Conflict -...

The Reboot Podcast ·

2021/07/13

In moments of conflict, it can be difficult to stay present amongst our discomfort. However, when we lean into love and compassion we might begin to see conflict in a generative light. In this episode of the Reboot Podcast, Jerry is joined by Regina Smith, MA and Amanda Aguilera, PsyD, experts in the field of power dynamics, conflict, and equity. In this conversation, Regina and Amanda examine and characterize the intersectionality of power dynamics and expound on the various ways power is conferred

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50:55

Reboot Extra #7: Women’s Conversations - I Am Enough:...

The Reboot Podcast ·

2021/06/29

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 inside job to keep ourselves clear-headed and attuned with our inner knowing, regardless of what the world

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45:28

#146 - The Cost of Failure - with Tom Eisenmann &...

The Reboot Podcast ·

2021/06/15

What are the factors that contribute to the failure of almost 90% of startup ventures? In this episode, Jerry sits down with author and Harvard Business School professor Tom Eisenmann to discuss the patterns that often precipitate the vast majority of startup failures. The pair take a closer look at how the advice to “fail fast” often leads founders to false start — risking capital and time on the wrong solutions. They shine a light on the pressure founders feel to grow the business rapidly, the

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46:46

#145 - Facing the Monster (in Your Head) - with...

The Reboot Podcast ·

2021/06/01

Suneel Gupta is an entrepreneur, Harvard professor, and author of “Backable: The Surprising Truth Behind What Makes People Take a Chance on You.” In this episode, Suneel chats with Jerry about his personal struggles with fundraising and how it led him to attend a Reboot Bootcamp. They host a larger conversation around identity, the way our fears keep us small and safe, and why living and leading from our fullest selves requires confronting the monster in our head. Leave us a review on Apple

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22:39

Wisdom for Work #9: Navigating Power Differences To...

The Reboot Podcast ·

2021/05/18

In our coaching practice, one of the most common questions we receive from investors is, “How do I build more trusting and impactful relationships with leaders in my portfolio?” As coaches, we believe the core challenge that limits the ability for founders and investors to connect in a more collaborative way is rooted in the dynamics of power. In this short clip, Dan Putt, Reboot Co-founder and Director of Client Engagement and Reboot’s Director of Coaching, Andy Crissinger define the three

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52:11

#144 - The Stories We Tell Ourselves - with Ryan...

The Reboot Podcast ·

2021/05/05

This being human is a profoundly awesome adventure; our lives are peppered with moments of happiness, joy, and wonder, but our experiences can be messy, exhausting, and heavy too. As leaders, how do we manage the cacophony of emotions that we inevitably carry with us to the workplace? What holds us back from opening up, sharing, and being true with our colleagues, especially when we’re struggling? Ryan Caldbeck is the Founder and Executive Chairman of CircleUp. In this episode, Ryan opens up about

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49:13

#143 - We're All Carrying Something - with Gino Zahnd...

The Reboot Podcast ·

2021/04/20

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 question asked at Reboot Bootcamp gave him the courage to share his health struggles with his team and

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22:18

Wisdom for Work #8: Coordinated Action: Making and...

The Reboot Podcast ·

2021/03/30

At Reboot, we believe making and keeping commitments is a necessary building block for sustained collaboration and growth within an organization. In our coaching we’ve seen first hand the damaging impact the breakdown of commitments can have on trust, performance, and workplace culture. In this clip, Andy Crissinger and Jeff Riddle share why coordinated action, the process of requesting and making commitments, requires good hygiene around elements of communication, especially as organizations adapt

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45:30

#142 - Signal & Noise - with Jeremy Bloom & Jerry...

The Reboot Podcast ·

2021/03/16

Jeremy Bloom is a 3x World Champion, 2x Olympic Skier and former football player for the Philadelphia Eagles and the Pittsburgh Steelers. He is the founder of Wish of a Lifetime and CEO of Integrate, a venture backed marketing software company. In this conversation, Jeremy shines a light on the burdens elite athletes face and describes the toll it has on mental and emotional well being. Jerry and Jeremy discuss the striking parallels between the pressures elite athletes encounter and the everyday

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15:18

Wisdom for Work #7: The Value of Feedback - with Andy...

The Reboot Podcast ·

2021/03/02

At Reboot, we believe feedback can be one of the best ways to maintain relationships and strengthen connections within an organization. In this clip, Coaches Andy Crissinger and Jen Cody share why creating an underlying culture that supports the health and safety of an organization through feedback is such a valuable leadership tool. 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

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48:23

#141 - What Is My Work To Do? - with Nathan Lustig &...

The Reboot Podcast ·

2021/02/16

After spending the last seven years routinely moving from country to country in Latin America, Nathan Lustig’s nomadic life was upended when the Coronavirus pandemic began to grip the entire world. As the Managing Partner of Magma Partners, Nathan became accustomed to a transient lifestyle as he worked to build his early-stage venture capital firm. Now facing the first prolonged travel hiatus of his recent career, Nathan sits down with Jerry to unpack the ways in which his aversion to setting roots

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01:02:58

Reboot Extras #8: Women’s Conversations - Feminine...

The Reboot Podcast ·

2021/02/04

In this fourth episode of our Women Conversation series, Reboot Coach and creator of The Third Jamie Kim sits down with Bunny and Taran Ghatrora, co-founders of Blume, a venture-backed self-care company. Taran and Bunny open up about their experience navigating the unforeseen challenges brought about by COVID and describe how their own self-care needs have shifted in the last year. The trio hosts a discussion around the unique hurdles many BIPOC female founders face when obtaining VC funding, and

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01:09:21

#140 - From Heartbreak, Through Resilience, To...

The Reboot Podcast ·

2021/01/25

In this fresh release, Jerry sits down with past client, former CEO of Etsy, and fellow executive coach, Chad Dickerson. In this episode, Chad describes the shift from CTO to CEO and the anxiety he experienced in the months after his transition. He gives insight into some of the unique challenges he faced in his six years as CEO of Etsy, and opens up about his painful departure from the company. Jerry and Chad contemplate what it means to lead with compassion, humanity, and integrity, and consider

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252 results

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