The Reboot Podcast - podcast cover

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.

Episodes

#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 and relate to others from a more informed place. In this podcast, Jerry sits down with Brad Feld and David Jilk, co-authors of "Entrepreneur's Weekly Nietzsche: A Book for Disruptors". The duo, who’ve shared a personal and professional relationship for nearly f...

Apr 12, 202252 minEp. 156

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 on breathwork, sitting with uncertainty, and discovering what it means to reconnect with the cradle of our lovingkindness. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Compu...

Mar 29, 20228 min

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 her everyday life. She describes her daily gratitude practice and details how leaning into joyful pursuits has reinvigorated her creativity and boosted productivity. Leave us a review on Apple Podcasts! Follow our step by step guides...

Mar 17, 202249 min

#155 - The Heart of the Matter - with Simon Maltais & Jerry Colonna

As the Coronavirus pandemic continues to shape our lives, many of us are flat-out exhausted. While this enduring moment in time has impacted us all, the prolonged nature of this global public health crisis has left healthcare workers feeling physically and mentally exhausted. Burnout, it’s a topic that we often address on the Reboot Podcast, and a term we’ve all been hearing more and more over the course of the past few years. For cardiac surgeon Dr. Simon Maltais, long hours in a demanding work...

Mar 06, 202249 minEp. 155

#154 - Untying the Knot of the Heart - with Duff McDonald & Jerry Colonna

When we’re so committed to being right about our own reality, we miss things happening right under our nose. Egos are handy, but they can be limiting to the amount of joy we experience in life if we let them lead the way. In this episode Duff McDonald, journalist and author of "Tickled: A Commonsense Guide to the Present Moment", recounts how the quiet of quarantine shocked him out of his narrow perspective of living, and turned his way of being on its head. Duff describes how the gift of fallow...

Feb 15, 202254 minEp. 154

Reboot Extra #10: Drawing From the Power of Our Ancestors: A Guided Visualization with Jamie Kim

How often do you connect with those who came before you? What do you know about them? What was life like for them? What did they live through? What were their unfulfilled dreams? What stories are still alive in your family to this day? When doing the work of learning about our past, we can forget that we are here because of many generations of love expressing itself. In this podcast Extra, Jamie Kim offers a visualization to connect with those who came before you and to feel the magnitude of tha...

Feb 08, 20226 min

Operator's Manual #4: On Modeling Self-care and Building the Machine - with Ali Schultz & Jerry Colonna

In this episode of our Operator's Manual series, Ali and Jerry consider how the health and resilience of an organization can be directly tied to the CEO’s own modeled behavior around self-care. Jerry reminds us that the CEO’s job is to build the machine that builds the products and services, not to build the products and services. 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 ...

Jan 25, 202213 min

#153 - Everyone Is Scalable - with Matt Blumberg & Jerry Colonna

For our first episode of 2022, Jerry sits down with Matt Blumberg, founder and CEO of Bolster, a marketplace for on-demand executive and board talent. In this conversation, Matt describes how the knowledge and insight he gained during his 20 year run as the founder and CEO at Return Path, Inc. prepared him for the uncertainty that comes with being a second-time founder. The pair discuss Matt’s latest book, Startup CXO, which serves as a handbook for defining the functional competencies and skill...

Jan 11, 202242 minEp. 153

Operator's Manual #3: The Great Re-Examination: How Do You Want To Spend Your Minutes? - with Ali Schultz & Jerry Colonna

The phrase, “The Great Resignation,” has become abundantly popular in the media over the recent months. In this episode, Ali and Jerry discuss how pandemic life has ushered forth larger questions around how we want to work and live. They consider how this unique period in time has brought about a rare opportunity for companies, leaders, and employees to re-examine their values, and to put people back at the heart of our organizations. Leave us a review on Apple Podcasts! Follow our step by step ...

Dec 14, 202115 min

Operator's Manual #2: What Does It Mean To Step Back and Let Others Lead? - with Ali Schultz & Jerry Colonna

The more we work with clients, the more we see leaders longing for pieces of wisdom around the parts of the job that aren't necessarily in any playbook. In this conversation, Ali Schultz sits down with Jerry to explore the question: What does it mean to step back and let other people step up and lead? 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 newsl...

Dec 02, 202114 min

Operator's Manual #1: What IS the Job of the CEO? - with Ali Schultz & Jerry Colonna

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 C...

Nov 18, 202111 min

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

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-wort...

Nov 04, 202155 minEp. 152

#151 - The Heartbreak of Every Day - with Nitin Agrawal & Jerry Colonna

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 prepa...

Oct 13, 202149 minEp. 151

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

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 hi...

Sep 28, 20211 hr 1 minEp. 150

Reboot Extra #9: 360° Reviews: Feedback as a Powerful Tool for Leadership Growth - with Andy Crissinger & Courtney Joyce

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 Crissinge...

Aug 24, 202121 min

#149 - Tending the Garden of Democracy - with Amy McGrath & Jerry Colonna

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, "...

Aug 11, 202150 minEp. 149

#148 - When Your Company Grows You - with David Hieatt & Jerry Colonna (re-release)

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 ...

Jul 27, 202152 minEp. 148

#147 - Power, Progress, and Generative Conflict - with Regina Smith & Dr. Amanda Aguilera (re-release)

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 confe...

Jul 13, 202154 minEp. 147

Reboot Extra #7: Women’s Conversations - I Am Enough: Vulnerability, Imposter Syndrome, and Confidence (re-release)

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 w...

Jun 29, 202149 min

#146 - The Cost of Failure - with Tom Eisenmann & Jerry Colonna

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...

Jun 15, 202143 min

#145 - Facing the Monster (in Your Head) - with Suneel Gupta & Jerry Colonna

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 Podc...

Jun 01, 202144 minEp. 145

Wisdom for Work #9: Navigating Power Differences To Build Better Relationships - with Andy Crissinger & Dan Putt

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 dime...

May 18, 202121 min

#144 - The Stories We Tell Ourselves - with Ryan Caldbeck & Jerry Colonna

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 abo...

May 05, 202150 minEp. 144

#143 - We're All Carrying Something - with Gino Zahnd & Jerry Colonna

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 ul...

Apr 20, 202148 minEp. 143

Wisdom for Work #8: Coordinated Action: Making and Maintaining Commitments - with Andy Crissinger & Jeff Riddle

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 ad...

Mar 30, 202121 min

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

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 everyda...

Mar 16, 202143 minEp. 142

Wisdom for Work #7: The Value of Feedback - with Andy Crissinger & Jen Cody

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 ...

Mar 02, 202114 min

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

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 ro...

Feb 16, 202146 minEp. 141

Reboot Extras #8: Women’s Conversations - Feminine Leadership, Self-care, and Fundraising for BIPOC Founders

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, an...

Feb 04, 20211 hr 1 min

#140 - From Heartbreak, Through Resilience, To Equanimity - with Chad Dickerson & Jerry Colonna

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 consid...

Jan 25, 20211 hr 7 minEp. 140