The Reboot Podcast

“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 company’s mission. In their session, Jerry helps to illuminate how the governors of our ego serve to protect us from feeling the shame and humiliation of being found out as the incompetent that we suspect we are, and supports Forest in unpacking the character structures that reify his feelings of imposter syndrome. As their conversation progresses, they shift to discuss the white savior model, why addressing systemic problems require systemic solutions, and with help from James Baldwin, Jerry reminds us all why nothin

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 stand still and courageously, tenderly examine his life with honesty. Jerry and Marcus chat about times of hardship and the gift of opportunity and inquiry that lies in adversity, if only we are willing to see it. 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 newsletter to stay up to date on all our episode releases.

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 place-based to remote communities has encouraged innovation, collaboration and reflection with organizations and how this unique moment in time has provided companies the opportunity to create environments of belonging that enhance growth of the individual and the collective as a whole. 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 newsletter to stay up to date on all our epi

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 comes with the question, “what’s next for me?”. Jerry notes what happens when we merge our sense of self with an external entity and reminds Fritz that with the formation of his new company, Zipcan, he has been given a beautiful opportunity to rethink the way he wants to relate to work and to design his second act of life. 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 newslet

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 & CEO of Wellthy & Co. Feeling stagnant and unsure, Shizu looks to Jerry for support and clarity in discerning the best future for her company and herself. Like most leaders in a position of power, Shizu feels the pull of responsibility to her investors and employees to, “Do the right thing.” As the conversation develops, Jerry aids Shizu in unpacking how intergenerational familial trauma may have manifested as a set of subroutines, directly influencing how she shows up in leadership and life. Shizu begins to ackno

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 businesses receive funding. Jerry and David chat about the freedom and risk associated with any entrepreneurial venture and consider the importance of smaller businesses and the immense value they provide their local communities. 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 Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newslett

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 a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/   Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

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 origin when greater opportunities opened up abroad. Now a naturalized citizen of the United States, Leslie admits to feeling out of place and unwanted in her adopted home. In hearing her story, Jerry reminds Leslie that in turbulent times, often the best gift we can give ourselves is to search for and connect to a greater sense of purpose. For Leslie, the question “Why do I do what I do?” leads her back to family —past, present and future. Jerry encourages Leslie to remember the sacrifices of her ancestors (as well

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 given him the space to reaffirm the company’s values and solidified the importance of taking care of not only the people of his organization but the community as a whole. Jerry and David acknowledge the value of servant leadership, remark on the beauty of team building, and consider what happens when your company grows you. 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 news

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 his confidence as a leader. Jerry and Erine discuss insecurities, faith, and why loving your inner critic is critical for compassionate leadership. 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 newsletter to stay up to date on all our episode releases.

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 miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

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 on the various ways power is conferred in our culture (and our workplaces). They highlight how conflict avoidance is often most detrimental to those in the down power role and why expanding our capacity to be in conflict is necessary for progress. The conversation explores how cultivating a positive outlook towards conflict supports our ability to engage empathetically and skillfully when moments of friction arise. By introducing the notion of generative conflict (and the idea of radical collaboration), they underscore

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 removing the barriers to belonging in the workplace and share that when those with whom we work feel a true sense of belonging, trust and productivity increase within an organization. They examine the power of pronouns, make the distinction between allyship and advocacy, confront the ways in which our biases direct us, and describe why leadership without inclusivity is not true leadership. 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-it

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! 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 newsletter to stay up to date on all our episode releases.

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 from a place of integrity and wholeness. Rha notes that personal commitment to doing the work that supports mental, spiritual, emotional, physical well-being is the ultimate prerequisite for leadership and Jerry stresses the importance for those who hold power to do their own work in order to reduce violence to our communities, the planet, and themselves. 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 a

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 business, reflecting that failure is a foundational part of the vast majority of startup journeys. Avni describes how Jerry’s open and honest question of, “Are you ok?”, revealed a well of unprocessed emotions and kick-started the inquiry process about her next steps as an entrepreneur. Avni determines that while Poppy as an entity no longer exists, her overall mission and purpose that drove its existence lives on in her new company, Modern Village. As she sublimely reflects, the collapse of her previous business has dri

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 Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/   Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

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 our being and the truth at our core. In this episode of the Reboot Podcast, you’ll meet Thiyagarajan (Rajan) Maruthavanan, Partner at Upekkha, an Indian SaaS Accelerator. With all the uncertainty that has emerged in the face of the novel Coronavirus, Rajan comes to Jerry holding questions around the future of the business and how best to support the founders which are struggling. What follows is a thoughtful conversation about the power of radical self-inquiry, the undeniable truths that emerge when we align with our hea

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 a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

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 experiences with their children. Feeling “in the middle of a tornado,” Danny reached out to the Reboot Podcast looking for guidance through a particularly challenging time. What unfolds is a forthright conversation about the experiences of our youth and ways in which the conditions of our formative years are often unknowingly etched upon our lives. As Jerry tenderly acknowledges, the conditions we survive as children often become the conditions necessary for our thriving as adults. Through the process of inquiry and with Je