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, 2021•1 hr 7 min•Ep. 140
Sydnie L. Mosley is an artist-activist, educator, and Artistic Director of SLM Dances, a New York City-based collective of women and nonbinary people who tackle issues of race and gender through experimental dance. In this conversation, Sydnie shares how expression through dance necessitates deep presence and connection to our bodies and highlights the ways in which its practice supports self-actualization and living into the fullness of our humanity. Jerry and Sydnie contemplate the real conseq...
Jan 09, 2021•57 min•Ep. 139
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 Ingrid define joy (and how it can be differentiated from happiness) and consider the role it plays ...
Dec 17, 2020•45 min•Ep. 138
“Not everything that is faced can be changed. But nothing can be changed until it is faced.” - James Baldwin In this release, Jerry sits down with Forest Richter, Co-founder and CEO of Uncrowd.io, a software platform that serves to connect underrepresented startup founders with investors. Forest shares how his ongoing battle with imposter syndrome has undermined his self-confidence and has called forward deeper questions around whether he, as a cis-gendered white man, can effectively execute the...
Dec 04, 2020•55 min•Ep. 137
Joining Jerry on this episode of the Reboot Podcast is Marcus Aurelius Anderson, author of “The Gift of Adversity: Overcoming Paralysis and Pain to Find Purpose”. While preparing to deploy with the US Army, Marcus suffered a severe spinal cord injury which left him paralyzed from the neck down. In this conversation, Marcus shares how turning to gratitude provided the antidote to the denial and anger he felt in the aftermath of his accident, describing how his paralysis forced him to literally st...
Nov 12, 2020•44 min•Ep. 136
In this release, Jerry welcomes back close personal friend Brad Feld to the show. In his sixth Reboot Podcast appearance, Brad (author, and co-founder of Foundry Group and Techstars) introduces listeners to the concepts highlighted in his newest book, "The Startup Community Way." Jerry and Brad explore the impact COVID-19 has had on the state of work, and consider how virtual environments influence and enable connection across broader startup communities. They contemplate how the shift from pl...
Oct 30, 2020•53 min•Ep. 135
For many founders, the ups and downs of the startup rollercoaster feel like a natural component of the entrepreneurial journey, but what happens when the ride becomes too much and what’s best for you, and the company, is to walk away? In this episode of the Reboot Podcast, Jerry sits down with Fritz Brumder, co-founder and former CEO of Brandlive. Fritz speaks candidly about his exit as CEO, describing how the process was simultaneously painful and relieving, and admits to the uneasiness that co...
Oct 13, 2020•52 min•Ep. 134
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 fallen out of alignment. Our guest on this episode of the Reboot Podcast is Shizu Okusa, Founder & CE...
Sep 24, 2020•1 hr 1 min•Ep. 133
For this podcast release, Jerry sits down with David Sax to chat about his latest book, "The Soul of an Entrepreneur: Work and Life Beyond the Startup Myth." In their conversation, David outlines how the archetype of the hero entrepreneur has been glorified by Silicon Valley and illustrates how this particular prescriptive formula for startup success can be limiting and exclusionary for under-represented groups. David addresses how romanticizing the startup myth stymies creation and limits what ...
Sep 10, 2020•51 min•Ep. 132
What is psychological safety and why is it so important for the success of our teams? In this clip, Reboot Coaches Andy Crissinger and Ali Schultz, share what we can learn from horses about group dynamics and highlight some best practices for leaders looking to cultivate psychological safety in their teams and workplaces. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave ...
Sep 04, 2020•30 min
Joining Jerry on this episode of the Reboot Podcast is Leslie Feinzaig, Founder & CEO of the Female Founders Alliance, whose mission is to accelerate the success of venture-scale, women and non-binary founded companies. In this conversation, Leslie shares how attempting to lead and manage her team amongst the fallout of a global pandemic has led her to shift her thoughts to family in distant countries. The granddaughter of Holocaust refugees and a Costa Rican native, Leslie left her country of o...
Aug 27, 2020•1 hr 9 min•Ep. 131
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 ...
Aug 13, 2020•52 min•Ep. 130
On this episode of the Reboot Podcast, we introduce you to Erine Gray, founder of Aunt Bertha, a nationwide search and referral platform for connecting people in need with available government and charitable programs. In his time with Jerry, Erine recounts growing up as a poor child in a small town and how the experience repeatedly left him feeling judged and unaccepted, triggering feelings of anger and shame. He opens up about his struggle to shake the underdog mentality and how it undermines h...
Jul 30, 2020•53 min•Ep. 129
Inquiry is an incredibly central and important skill, but it’s often underemphasized or even overlooked in the world of leadership. In this clip, coaches Andy Crissinger and Chris Vandenbrink share why adding inquiry as an additional tool in your toolkit can be in service of you, your team, and the work that you’re trying to do together. 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 m...
Jul 23, 2020•18 min
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, Co-founders of Evolving Dynamics, 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 ...
Jul 16, 2020•54 min•Ep. 128
In this release, Jerry sits down with leading diversity and inclusion expert Jennifer Brown to explore her latest book, How to Be an Inclusive Leader: Your Role in Creating Cultures of Belonging Where Everyone Can Thrive. In this conversation, recorded at the beginning of 2020, Jennifer reveals why inclusive leadership is not only risky, but often uncomfortable, and why discomfort is necessary for individual and organizational growth. Jerry and Jennifer analyze why true inclusivity requires rem...
Jun 26, 2020•54 min•Ep. 127
The fundamental unit of doing that great work is conversation. Conversations happen easier, clearer, and more harmoniously if we can connect as human beings, look each other in the eye, trust, and feel safe naming what’s up for us. In this clip, coaches Andy Crissinger and Chris VandenBrink share Reboot’s Red-Yellow-Green model for check-ins and how it’s implementation can shift the tone of how you relate to folks and hold meetings such as 1-1’s and offsites. Leave us a review on Apple Podcasts!...
Jun 18, 2020•17 min
On this episode of the Reboot Podcast, Jerry sits down with Rha Goddess, author, entrepreneurial soul coach, and founder of Move the Crowd. In this conversation, which centers around Rha’s new book The Calling: 3 Fundamental Shifts to Stay True, Get Paid, and Do Good, Rha describes the ethos of soul work and shares why calling forth the qualities and attributes that live in the truest and purest expression of ourselves are crucial for those who lead. Jerry and Rha explore what it means to lead f...
Jun 12, 2020•54 min•Ep. 126
Feelings of isolation and loneliness have been well documented amongst today’s leaders. That’s why the simple question “Are you ok?”, asked with genuine concern, can elicit such a profound impact for those who are struggling through a tough time, such as shutting down a business like Avni Patel Thompson. At the time of this recording, Avni was in the wake of shuttering her previous company, Poppy. In this exchange, Jerry and Avni discuss the trauma and pain that go hand in hand with closing a bu...
May 29, 2020•55 min•Ep. 125
The ability to differentiate between transition and change is important for leaders to understand when attempting to lead groups of people through uncertain times. In this short clip, Andy Crissinger, Reboot’s Director of Coaching, introduces a helpful framework for leading teams through times of transition. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Yo...
May 21, 2020•17 min
As leaders, necessity requires that we spend ample time designing for the future and building safety nets for the unknown, but what happens when life throws the unexpected our way and our best laid plans are torn asunder? In times of turbulence, it’s not uncommon to feel suspended in space. To combat the unease of unknowing we search desperately for a map that might provide guidance in our path forward. In looking to the external, we often lose sight of the compass rose that lives deep within ou...
May 15, 2020•56 min•Ep. 124
As leaders, you have a choice, first and foremost, in how you process the information that's coming at you at any given time. In this clip, Andy Crissinger, describes Information Processing Choices, a framework and tool that Reboot often uses in our leadership development engagements, bootcamps, and in one-on-one coaching. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave...
May 12, 2020•15 min
One of the greatest missteps a leader can take is to live an unexamined life. When our subroutines run unchecked beneath the surface, our work, our organizations and our relationships are unwittingly hijacked by the traits we consign to the shadows. As leaders, the greatest gift we can give to ourselves and others is to choose to make the unconscious conscious. In this episode, Jerry is joined by Daniel Feltsman, Founder of Lina, an online platform for helping parents share wisdom and life exper...
May 02, 2020•56 min•Ep. 123
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: - How To: Leave a Review on Your Computer: - How To: Leave a Review on Your iPhone: Never miss an episo...
Apr 23, 2020•15 min
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 Ingrid define joy (and how it can be differentiated from happiness) and consider the role it plays ...
Apr 16, 2020•45 min•Ep. 122
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 about how to create meaningful connections in virtual environments. This conversation tackles the histor...
Apr 03, 2020•51 min•Ep. 121
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...
Mar 13, 2020•49 min
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 consider how disagreements can trigger feelings of shame, and how attempts to safeguard ourselves fr...
Feb 27, 2020•49 min•Ep. 120
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 iTunes! Follow our step by step guides: - How To: Leave a Review on Your Computer: - How To: Leave a ...
Feb 14, 2020•42 min•Ep. 119
“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 cultivates trust, reaffirms feelings of safety and builds spaces of belonging. Together they consider the ...
Jan 30, 2020•49 min•Ep. 118
