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The Reboot Podcast on Smash Notes

The Reboot Podcast podcast.

December 28, 2019

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 with Smash Notes

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-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

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

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 driven her into greater alignment to her life’s Work, leading her to exactly where she needs to be. 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.

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 hearts center and how those values ultimately provide clarity around purpose in unpredictable times. 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.

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 Jerry’s support, Danny begins the first step in making the unconscious conscious by asking, “What subroutines am I running?” 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.

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

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 in our lives. Ingrid describes how humans are hardwired to find joy and underscores the extraordinary ways in which it serves to combat stress and fortify resiliency in times of adversity. Ingrid reminds us that times of stillness can broaden our capacity for finding delight in ordinary moments, and how those small joys can sustain us in arduous times. 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.

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 history and development of Reboot Circles and outlines the ways in which leaders benefit from spaces of trust. The coaches also break down the essential components needed to establish and uphold a successfully safe space and share their advice for those who may be looking to implement peer coaching in their own organizations. 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.

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 throws our way in terms of perceptions, biases, and double standards. How do we, as women, stay in our own bodies, hold fast to our own truths, and not view ourselves through the eyes and expectations of others in the world-at-large? Who do you choose to be? What life do you want to lead? In this third episode of our Women Conversation series, Reboot Co-founder Ali Schultz joins fellow coaches Ann Mehl, Heather Jassy, and Miriam Meima for an exploration of how imposter syndrome grips women, the masks they feel they need to wear, and all that gets in the way of women feeling their inherent enoughness. 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 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 from those feelings often get externalized as blame towards those with which we are in conflict. They highlight how turning to wonder (in conjunction with compassion and empathy) when confronted with conflict can bridge the gap of misunderstanding and acknowledge that not all conflicts will come to a resolution, sharing some helpful practices for breaking the conflict cycle.   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 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 Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

“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 business case for love, reflecting on its ability to sustain healthy teams, drive personal growth, and foster self-actualization, ultimately lending a hand in providing spaces for humans to come together and do their best work. To close out their discussion, Steve highlights how companies built around cultures of love typically benefit from increased customer loyalty, boosts in profitability, and capture higher percentages of market share. Leave us a review on iTunes! 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.

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, and working through it all. Together, Ali, Heather, and Ann (who are both mothers of two) address some of the singular challenges women face when it comes to family planning and share their own unique experiences as mothers in the workplace. We hope you’ll enjoy this conversation which serves to tackle some of the questions our clients work through such as, “Is motherhood right for me? When is the right time to start a family? How do I manage maternity leave and navigate the return to work?” and much more. *Please note that this episode contains explicit language and may not be suitable for young ears. Leave us a review on iTunes! 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.

Tracy Lawrence, Co-founder and CEO of , 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 her approach to the latest company experiment but it also might affect her own leadership and bring her and her company deeper into alignment. Leave us a review on iTunes! 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 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 have provided the opportunity for reflection and personal growth. Dylan recognizes that talking honestly and openly about his adversities lessens his feelings of loneliness and opens his heart to the salve of community. Jerry emphasizes the power of wounds and implores Dylan to remember this period of pain and adversity and allow his experience to broaden his capacity to extend compassion to others. As a final offering, Jerry proposes how working with feelings around attachment and grief could benefit Dylan on his journey of radical self-inquiry. Leave us a review on iTunes! 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

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, as mothers, healers, and coaches. In this first episode, Reboot Co-founder Ali Schultz and fellow senior coach Heather Jassy acknowledge and reflect on the many ways in which women are affected by gender biases in the workplace and the ways in which those barriers can distort and conflate their notions of value and self-worth. Ali and Heather discuss the ‘crabs in a bucket’ theory and unpack the phenomenon of tall poppy syndrome. Finally, they highlight the importance of setting boundaries, making space, and connecting to your truth. *Please note that this episode contains explicit language and may not be suitable for young ears. Leave us a review on iTunes! 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

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 consider how our values shape the way in which we (and our companies!) show up to meet the world. Yancey sheds light on how the Western World has shifted away from a culture that highly values community, purpose and fairness, and has instead placed focus and value on decisions that maximize financial gain. In order to tackle the major problems facing the world today, Yancey calls for a radical shift in how we view rational self-interest, proposing that self-coherence, or making decisions that are aligned with who you really are and want to be in the future, is the key to expanding our world view. When we come into alignment with ourselves, we are building a greater capacity to see the ways in which our choices could have a greater influence beyond ourselves. In shifting from a ‘me’ to an ‘us’ way of looking at the world, we open ourselves up to the ability to make choices that will create a fairer and more fulfilling world to live in. Leave us a review on iTunes! 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

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 acknowledge the ways in which the shoulds of the past and the anxieties of the future limit herself from fully stepping into the now. Jerry reminds Shizu that radical self-inquiry is the catalyst for unraveling the unconscious threads that dictate our lives, the key to alignment between inner and outter, and the driving force for strengthening purpose and meaning. Leave us a review on iTunes! 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

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 with entrepreneurs through those challenges. In listening to this conversation, we hope you’ll consider: In my own work, what are my values? What are my priorities? What would it mean to invest in being myself? Leave us a review on iTunes! 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

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, mindfulness, compassion, and the practice of loving-kindness are at the crux of radical responsibility. By embracing ownership for each and every circumstance we face in life (without assigning blame or cultivating a victim narrative) we are better able to reflect upon our current situations and assess creative solutions for moving forward. In considering radical responsibility, Jerry and Fleet tackle three important questions: How am I complicit in creating the conditions I don’t want? In what way can I take ownership for circumstances that I may not have any complicity in? What can be gained from holding your seat amongst the chaos of life? Radical Responsibility ​https://fleetmaull.com/training/radical-responsibility/   Leave us a review on iTunes! 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

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 shares her story and the singular obstacles she’s been summoned to encounter. A former corporate litigator, Amy Nelson is now the CEO and founder of the Riveter, a workspace which provides support and equal opportunities for women leaders and changemakers. Born in Seattle in 2017, The Riveter has experienced explosive expansion - with five locations being built in the first 16 months. As a result, Amy is now facing down the many hurdles that emerge during a period of rapid scaling. In this conversation with Jerry, Amy expounds on a few of the barriers she’s come up against when raising capital and what it means to take her seat as a leader . Jerry introduces Amy to Parker Palmer’s image of “The Tragic Gap,” recognizing that Amy has been called to stand in the space between the world that is, and the world that is possible. Carrying the burden for all female entrepreneurs to forge a future where women not only have equal opportunity but a true place of belonging as leaders, forging a system where all individuals are worthy of the freedom to actualize in the fullness of who they are. Leave us a review on iTunes! 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

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 Products That Build Successful Businesses. Jerry and Jules note how loneliness often accompanies the maker experience and touch on the importance of peer support in the maker community. Jules expands on how tenacity is integral for a maker’s success and how learning to tackle fear creates more resilient leaders. As Pieri proclaims, “people who manage to pursue their ambitions learn to recognize the fear and walk into, rather than practice avoidance.” Leave us a review on iTunes! 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  

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 show up, meet, and communicate with those around us, and how stepping into adulthood requires that we examine the negative parts of ourselves that we don’t want to own. We hope you’ll enjoy this fireside chat, mini coaching session, and Q&A all wrapped up in one! Leave us a review on iTunes! 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

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 congruence via communication is paramount. On this episode of the Reboot Podcast, Sara and Mathias turn to Jerry for support in establishing a blueprint for their new business partnership, specifically looking to gain insight on how to communicate successfully across a large geographical barrier. In this conversation, Jerry puts forth the notion that all human interactions in relationships (whether work or personal) stem from our desire to feel love, safety, and belonging. Jerry helps Mathias and Sara unearth the ways in which their old patterns of communication may be tied to their personal fears around belonging. Jerry encourages Mathias and Sara to consider how exquisite communication built around empathetic connection grants them the opportunity to stand shoulder to shoulder as leaders and adults, offering them the chance to support each other in their journeys towards growing up. Leave us a review on iTunes! 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

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 from their experience. Jerry also explores many themes tackled in the book, including the radical nature of radical self-inquiry, the power of leading from your truest self, and the ways in which work provides the opportunity to continuously align our inner and outer selves. Leave us a review on iTunes! 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

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 of the best mediums for effecting positive change, Jeff founded Exposure Labs. Self-described as an ‘impact production company,’ their mission focuses on utilizing visceral, honest storytelling to enact change and enable open conversations on tough subjects. In this conversation, Jeff discusses the parallels of filmmaking and serial entrepreneurship, reflecting on how his new projects can generate the same feelings of uncertainty, thrill, and fear that often arise in early-stage startups. Jeff shares his journey into filmmaking and how he sees himself first and foremost as a problem solver. Together, Jerry and Jeff hold a dialogue on Purpose, pondering its elusiveness, why we chase it and the reasons we often seek our purpose in the ‘wrong’ places. Leave us a review on iTunes! 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

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 transitional period. While the transition in her professional career served as a catalyst for their conversation, Jerry encourages Alex to consider what may also be bubbling under the surface in her personal life. Alex opens up about finding joy in being present, recognizing that this break has afforded her the ability to reconnect to her body, her passions, and her community. Jerry notes that this pause, a time of contemplation and rest, provides a profound opportunity to shift Alex’s way of being in the world, granting her the freedom to redefine her definition of happiness and success. As she embarks on this new relationship with herself, the doors open for Alex to become the leader she wants to be. Leave us a review on Itunes! 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

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 to the version of ourselves we left behind. On this episode of the Reboot Podcast, we introduce you to David Ryan, former Managing Director and Co-founder of Corilla, a collaborative content tool for software teams. In this conversation, David reflects on his decision to shut down his organization and the period of transition it has heralded forward. David expresses gratitude for his time as CEO and explores embracing the uncertainty of stepping into the newest stage of his life as an author. As Jerry gently reminds David, life unfolds as a series of entrances and exits; we must all learn to softly close doors on previous chapters of our lives in order to fully open to what’s next. With each transition, we have the beautiful opportunity to reflect and grow from the experiences that have shaped us. Carrying the threads of the past onward, we weave the tapestry of our lives, creating the pattern for a story that is uniquely, undeniably yours. Leave us a review on Itunes! 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

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 uncommon for leaders to lean heavily on the startup handbook to better understand the ‘right’ way forward; however, as most leaders come to understand, what works in theory doesn’t always play out in practice, and at some point all responsible leaders must consider if the company they’re running is the company they aspired to build. On this episode of the Reboot Podcast, co-founders Chris Savage and Brendan Schwartz share how listening to their instincts led them to flip the script, throw out the startup handbook, and take back ownership of their video-software company, Wistia. Brendan and Chris remark on how buying out their investors released the pressure they felt to implement quick solutions for the sake of driving short-term growth and increasing revenue, and the way in which this shift opened the doors for a more creative and joyful work experience. In this conversation, Jerry, Brendan, and Chris propose an important question for all leaders, “What type of company do you want to work for?” Leave us a review on Itunes! 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

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 purpose, meaning, and making an impact on the world. Together, they explore the decidedly unpredictable nature of life, noting how our desire to control life as it unfolds is one of the greatest creators of stress and suffering. Jerry attests that our quest for equanimity stems from our ability to hold the plans of our lives loosely. It is only once we’ve released our grip on the playbook of life that we can truly  open to the beauty and fullness of our experience. With Jerry’s guidance, Khe comes to understand that in order to actually live his life, he must strive to stay present through the quiet moments that comprise his days. Leave us a review on Itunes! 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

Radical honesty - an open and authentic contribution, which lacks the intention of causing unnecessary pain and suffering, but serves to provide a mirror in which we can clearly reflect on the aspects of ourselves to which we are blind. On this episode of the Reboot Podcast, Jerry is joined by Patty McCord, former chief talent officer of Netflix, renowned for pioneering the use of radical honesty in the workplace. With her new book, Powerful:Building a Culture of Freedom and Responsibility, Patty aims to clearly define the best path for creating workplace cultures of high performance and profitability. In this conversation, Jerry and Patty consider how the implementation of radical honesty in our organizations serves to forge solid, supportive spaces where workplace safety is no longer defined solely by the assurance of employment, but contains space for team members to feel seen, heard and nourished to grow. Where skill sets are broadened, and diverse people with different ways of thinking come together without fear or expectation to judge or be judged. Wouldn’t that be a more powerful way of working? Leave us a review on Itunes! 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

For many of us experiencing periods of transition, our tendency might be to push through the unknowing of the “here and now” to focus solely on the “what’s next?” Yet, staying present serves us the most. While bobbing like a cork on the sea of life can be an uncomfortable and unsettling place, it also allows space for reflection, contemplation, and clarity to spring forth. For this episode of the Reboot Podcast, we welcome Shanley Knox, a writer, strategist, and social entrepreneur. In this beautifully honest and vulnerable conversation with Jerry, Shanley shares the major shifts she’s experienced in her personal and professional life, from the process of shutting down her company to the unknowns of first-time motherhood. With guidance from Jerry, Shanley tackles the lingering questions surrounding, “Who am I now?”,“Where do I go from here?”, and “How can I go about the future differently than my past?” Leave us a review on Itunes! 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

Here at Reboot we believe that the toughest conversations (with ourselves and others) are often the best catalyst for building bridges of understanding. When we refuse to allow ourselves to be stunted by fear and bravely open to perspectives beyond our own we welcome in a whole new way of seeing the Other. Since its inception in 2014, the Reboot Podcast has endeavored to provide a space where our guests and our listeners feel safe to tackle the difficult conversations that accompany our complex and complicated human lives. In keeping with our mission to host important, yet challenging conversations, (and in perfect time to celebrate Black History Month), we’re airing a recent conversation between host Jerry Colonna and Legacy 71 founder David McQueen. In this episode, Jerry and David touch on various topics, including race as a confining social construct, the notion of legacy, and how it can be reframed to not only exist as a mindset but also as a vehicle for building community and spaces of belonging. David also speaks to the unique challenges facing those in the Pan-African entrepreneurial community and the ways in which he, as a black man, aims to instill leadership lessons to people of color (and the organizations that they build) that will empower them to not only survive the system, but thrive. Leave us a review on Itunes! 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

Erin Frey and Ti Zhao, are the co-founders of Kip - an app which aids in locating a quality therapist and helps you measure your progress. In this episode, they sit down with Jerry to talk about the issues they run into and the importance of effective communication for a growing team. More importantly, they talk about what makes them tick and how their ability to work together as leaders is one of the most important things they can focus on at this stage of their company. This includes emotional literacy and helping each other regulate when tough issues arise. What does your cofounder (or partner) do when they are scared, angry, sad, triggered? Do you know what they need in that moment? Making time to discover the operating instructions for your partners solidifies not only your communication with each other, but it also solidifies your organization to defy the odds that 89% of startups fail. As Jerry notes, tending to good communication sets culture, direction, and creates the conditions in which raising capital is enhanced. Leave us a review on Itunes! 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

For many leaders, particularly entrepreneurs striving to build a vision, the experience of rejection hits close to home; oftentimes, it can feel as though there’s been a dismissal of our very soul. When faced with the fallout of rejection our initial response may be to thicken our skin or steel our reserve, building a wall behind which we suppress our sadness, our hurt, our tender selves. However, for all of us, another opportunity exists, one of compassion but also of strength; the opportunity to meet rejection as a warrior. On this episode of the podcast, Jerry is joined by Grace Belangia, Community Development Strategist for CONima and the Executive Director and Founding Member of the Clubhouse, a collaborative and innovative community for entrepreneurs. This past fall, Grace reached out to the Reboot Podcast looking for support navigating her feelings around rejection. In this conversation, Jerry works with Grace to uncover the root of her fears about rejection and how its threat may actually be the driving force that allowed her to discover her life’s passions. With Jerry’s guidance, Grace is encouraged to take an open-hearted stance toward rejection and reminded that standing as a warrior requires that we release ourselves from the notion that our self-worth is tied to the acceptance of people we deem powerful and influential. Jerry affirms that as we exist, we are lovable and whole, regardless of our perceived failures, and that ultimately, we, and we alone, hold the to key to determining our worth and belonging.   Leave us a review on Itunes! 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

There is real suffering out there, suffering that is causing violence. What are some of the causes of the suffering and how might we address those? It's a true honor to welcome entrepreneur, creator, and educator Konda Mason to the podcast for an important and timely conversation with Jerry. This discussion was recorded last week, and we thought it was really important to get this out sooner rather than later, particularly given the events in Orlando. Konda and Jerry address some of the source causes of this suffering, this pain, and what opportunities might lie in remembering we’re all in this together. This conversation will challenge you on your privileges and inspire you find new ways of connecting with people from all backgrounds. Links The Whole Person Economy - http://www.thewholepersoneconomy.com/konda-mason/ Konda Mason on Twitter - https://twitter.com/swamikondananda Impact Hub Oakland - https://oakland.impacthub.net Spirit Rock Meditation Center - https://www.spiritrock.org/instructordetails?calendarinstructorid=54375 Leave us a review on Itunes! 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

On this episode of the Reboot Podcast we welcome Joe Wilding, the co-founder and CTO of Boom Supersonic, a Colorado based company focused on reviving supersonic air travel. Although Joe has experienced successes and various advancements throughout his career, he grapples with a nagging feeling that he wasn't measuring up to the other “great leaders” in his field. Introverted and a highly-visual learner, Joe always felt he was wired just a bit differently from his peers. Throughout the past decade, Joe has transitioned out of supporting roles and into higher management positions. Recently, this has triggered thoughts around authenticity in leadership and has materialized the urge to align his inner and outer self in the workplace. With support from Jerry, Joe aims to tackle the question, ”What type of leader am I?” Jerry emphasizes to Joe that there are many ways to lead, and the tendency to constantly compare ourselves to others often serves in diminishing our ability to grow into our most authentic self, inhibiting our ability to become who we’re really meant to be. Leave us a review on Itunes! 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

For leaders in the modern world, dodging the constant bombardment of projected successes that others display across various media outlets can be exhausting.  Comparing ourselves to others can lead to an overwhelming sense of inadequacy, which often ripples out to thoughts of insecurity about our work, our relationships, and the way we are perceived by our peers. As Theodore Roosevelt so poignantly observed, “Comparison is the thief of joy.” By allowing our gaze to become so outwardly attuned, we create an internal roadblock against finding peace and equanimity within our own lives. On this episode of the Reboot Podcast, Jerry is joined by longtime friend and self-described serial entrepreneur, Steve Kane. In this discussion, Steve comes to Jerry with the lingering question, “When do we begin to know when enough is enough?” Together, they explore the pivotal role Steve’s father played in molding the baseline for determining his “enough,” and how his own radical self-inquiry supported Steve in making a difficult decision during the successful exit of his third startup, Gamesville. As they ponder the question of ‘enough,’ Jerry and Steve touch on the ways in which we, as humans, yearn for safety, love and belonging, and how, ultimately, our ability to expand our awareness of ‘enough’ is an act of continuous practice, one which allows us to take stock of our lives at any moment and truly consider, “When is enough, enough for me?” Links Steve Kane on Twitter - https://twitter.com/stevenkane Reboot Bootcamp - reboot.io/bootcamps Leave us a review on Itunes! 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

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 episode, you'll meet one female founder who generously shares her story and the singular obstacles she’s been summoned to encounter. A former corporate litigator, Amy Nelson is now the CEO and founder of the Riveter, a workspace which provides support and equal opportunities for women leaders and changemakers. Born in Seattle in 2017, The Riveter has experienced explosive expansion - with five locations being built in the first 16 months. As a result, Amy is now facing down the many hurdles that emerge during a period of rapid scaling. In this conversation with Jerry, Amy expounds on a few of the barriers she’s come up against when raising capital and what it means to take her seat as a leader. Jerry introduces Amy to Parker Palmer’s image of, “The Tragic Gap,” recognizing that Amy has been called to stand in the space between the world that is, and the world that is possible. She is carrying the burden for all female entrepreneurs to forge a future where women not only have equal opportunity but a true place of belonging as leaders, forging a system where all individuals are worthy of the freedom to actualize in the fullness of who they are. Links Amy Nelson on Twitter - https://twitter.com/amy_riveter "The Myth of CEO Work-Life Balance" - www.forbes.com/sites/amynelson1/…nce/#4692dfa919ae "The Three Unspoken Challenges of Women in Tech" - medium.com/@Reboot.io/the-3-un…n-tech-417f15651ca1 Leave us a review on Itunes! 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

Exploring one’s shadow is no easy undertaking. The idea of getting to know what Jung referred to as, “That which I do not wish to be” is rarely considered an exciting prospect. Yet we implore all leaders to be courageous and get to know and learn to work with their shadow. It is only when we do the work to make the unconscious conscious, that we are able to build true compassion for ourselves and others; freeing us to become the leaders we were born to become. James Hollis is a Jungian analyst, author and lecturer whose work has inspired and influenced us at Reboot. In this episode Jerry and James talk in depth about the Jungian concept of shadow, how shadow shows up in leadership, and what we can do once we become aware of our shadow. Links James Hollis' website - http://www.jameshollis.net Why Good People Do Bad Things - https://read.amazon.com/kp/embed?asin=B00164UXO2&preview=newtab&linkCode=kpe&ref_=cm_sw_r_kb_dp_OPjlybZY2VRM0 Episode #14 Shadow and Leadership - https://www.reboot.io/episode/shadow-and-leadership/ Episode #28 Reclaiming Shadow - https://www.reboot.io/episode/28-reclaiming-the-shadow/ Episode # 42 Building Relational Trust - https://www.reboot.io/episode/42-building-relational-trust-parker-palmer/ Leave us a review on Itunes! 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  

Have you ever asked yourself the question: I wonder if we’d be better off with someone else in my role? In this podcast, a listener, Kent Cavender-Bares from Rowbot comes to Jerry with a question a similar question about his superpower: “What if my deep integrity, my commitment to simply telling how it is, is the reason we’re unable to fundraise? Do I even have a Superpower? Wouldn’t Rowbot, be further along if someone else was leading?” Jerry and Kent explore the double edge of a superpower, and how the path through his challenges may lie in a new set of questions: How can I be even more like Kent? How can I embrace my superpower? How can I believe in myself? And why is that so damned important? Links Rowbot - www.rowbot.com Kent Cavender-Bares on Twitter - twitter.com/kbares Leave us a review on Itunes! 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 many leaders can attest, the harshest critics we face often come from within. Even when we feel confident in our work and our abilities, it’s not unusual for thoughts such as, “Am I doing enough?” to arise. Once our inner critic emerges, questions of guilt begin to creep in that we aren’t grinding nearly as long or as hard as those around us. As entrepreneurs, the challenge we face is discerning not only what triggers this internal voice, but recognizing what that voice, our Loyal Soldier, serves to protect. On this episode of the Reboot Podcast, Leonie Akhidenor, Head of Residential Development for View Bank Homes, works with Jerry to explore the roots of her own inner critic, tracing the emergence of Leonie’s Loyal Soldier back to a childhood environment where achievement and success were deemed paramount. Uncovering that, as she grew, Leonie’s constant fear of failure manifested as her superpower, providing an abundance of passion and grit which served to propel her professional success. But as Jerry notes, all superpowers contain a shadow side, and in this instance, Leonie’s fear also brings with it the anxiety and unease that comes with feeling like she isn’t measuring up to her peers. During their time together, Jerry touches on how the anxieties that we carry (and often our parents carry) are passed from generation to generation, and how the logic we used as a child and the survival techniques we developed may actually no longer be needed in our present situations, allowing us to recognize that we’re ok, just as we are. Links A Blessing For One Who’s Exhausted - https://soundcloud.com/storyweaver3/john-odonohue-a-blessing-for-one-who-is-exhausted Lovingkindness: The Revolutionary Art of Happiness - https://www.amazon.com/gp/product/157062903X/ref=dbs_a_def_rwt_bibl_vppi_i2 Little Dreamers - https://littledreamersonline.com   Leave us a review on Itunes! Follow our step by step guides: - How To: Leave a Review on Your Computer: https://www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: https://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.

Al Doan, former CEO of Missouri Quilt Company, speaks with Jerry Colonna about a journey that ultimately led him to walk through the fear and challenge of stepping down as CEO, to create the space for the life of his dreams to emerge. Links Missouri Quilt Company - https://www.missouriquiltco.com/ Al Doan on Twitter - https://twitter.com/drbillnye Signs you need to leave your startup - https://medium.com/@drbillnye/signs-you-need-to-leave-your-startup-7e7ce9284f0b CEO bootcamp - https://www.reboot.io/service/bootcamps/ Reboot Circles - https://www.reboot.io/service/peer-groups/ Episode #29 Who’s in your corner? With Carrie Barry - https://www.reboot.io/episode/29-whos-in-your-corner-with-carrie-barry/ Episode #77: Knowing You’re Not Alone, The Magic of Peer Groups - https://www.reboot.io/episode/77-knowing-youre-not-alone-magic-peer-groups-christine-carrilo-al-doan-keeley-tillotson-bryan-birsic   Leave us a review on Itunes! Follow our step by step guides: - How To: Leave a Review on Your Computer: https://www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: https://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.

Khe Hy spent 14 years in Financial Services and was successful by all signs, but his work and life felt ‘meh.’ Something felt disconnected from him as he suited up in the morning and turned off the finance switch in the evening. He opted for a life of more meaning and started RadReads, a passion project now grown into a community of sorts. But something still didn’t feel right for Khe. Even though he preached a lot about what’s important, he found that a hard talk to walk and instead found himself putting the most important things in his life - his wife and daughter - last on his list of priorities. Despite all of Khe’s efforts in meditation, mindfulness, and reflection, he struggled to figure out how to be present for his life. Instead, he found himself thinking about ideas, people in his network, and ways to improve. As a self-proclaimed life-hacker, he struggled to find the metrics and hacks to be present. As Khe and Jerry discuss, perhaps the answer to being present is deeper than hacks and metrics. Perhaps the clue lies in what he’s so afraid of. Links RadReads - https://radreads.co/ Khe Hy on Twitter - https://twitter.com/khemaridh   Leave us a review on Itunes! Follow our step by step guides: - How To: Leave a Review on Your Computer: https://www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: https://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.

Reverend Michelle Haunold Lorenz has dedicated the past 18 years of her life to her company, Gearhead, a magazine and record label that showcases the best of punk and hotrod culture. In her time spent as founder and CEO, Michelle has experienced first hand the ups and the downs that emerge when running and operating a business. Recently married, Michelle has begun to hear whispers of transformation, potentially signaling a transition into a new stage of life, one in which she finds herself questioning her life’s path and purpose. Looking for support and guidance, Michelle reached out to Jerry and Reboot Podcast. As she considers the past two decades, Michelle reflects on the challenges she’s faced - which run the gambit of downsizing and layoffs, declaring bankruptcy, and bouts of co-founder conflict - as well as the lessons she’s learned and the gifts she’s received in the process. As Jerry and Michelle work together, they consider the uniqueness of her journey, and the beauty of taking ownership of her life, and the ride that she is on - even if it’s not the adventure she expected. Links Sell the Apartment, Keep the Startup - ​https://www.gimletmedia.com/startup/sell-apartment-keep-startup-season-6-episode-3 Gearhead - https://www.gearheadhq.com/   Leave us a review on Itunes! 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.

Aging, the continuous passage of time, is a journey upon which we must all embark. As life unfolds before us, we may be naturally drawn towards a state of inquiry in attempt to discern the purpose and meaning in our soul. For many leaders, the draw can be to gaze upon external outcomes as a manifestation of our life’s meaning, allowing our worthiness to be derived from our relationship between mean and end. But what if we were to allow ourselves to abandon the question, “Does my life have meaning?” and instead consider, “How have I lived?” In this episode, Jerry is joined by speaker, activist, and friend of the Reboot Podcast, Parker J. Palmer, author of "On the Brink of Everything: Grace, Gravity, and Getting Old". Over the course of their conversation, Jerry and Parker contemplate the insights they’ve gained in the process of aging, the power of living life with kindness and gratitude, and the importance of remaining open to being human together. Links #14 – Shadow and Leadership – with Parker J. Palmer - https://www.reboot.io/episode/shadow-and-leadership #42 – Building Relational Trust – with Parker J. Palmer - https://www.reboot.io/episode/42-building-relational-trust-parker-palmer "On the Brink of Everything: Grace, Gravity, and Getting Old" - https://www.amazon.com/Brink-Everything-Grace-Gravity-Getting/dp/1523095431 - https://onthebrinkofeverything.com/ Czeslaw Milosz’s, Love - https://www.poemhunter.com/poem/love-2 Leave us a review on Itunes! 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.

Courage takes many forms, but how do we inject courage into our lives, our relationships, and how we build and tackle problems in our businesses? On this episode of the Reboot Podcast, Jerry is joined by Shelly Francis, Marketing and Communications Director for The Center for Courage and Renewal, and author of The Courage Way: Leading and Living with Integrity. In their conversation, Shelly and Jerry propose that the bedrock of leading with courage stems from our willingness to be open, honest, and vulnerable, not only with ourselves but with others. When we step into our wholeness, finding alignment between the inner and outer, the doors open, allowing us to lead and live our lives with integrity. From that place, we can lean on the foundations of trust we’ve built in our communities and our organizations to tackle the difficult moments when they arise. Links Shelly Francis on Twitter - https://twitter.com/shellylfrancis The Center for Courage and Renewal - http://www.couragerenewal.org The Courage Way: Leading and Living with Integrity - https://courageway.org The Möbius Strip - https://en.wikipedia.org/wiki/M%C3%B6bius_strip Leave us a review on Itunes! 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.

There’s an important question that we like to ask here at Reboot, which is, “ What type of company do you want to work for?” You’ll often hear Jerry propose this question in many of our podcasts because we believe it to be one of the most profound questions you can ask a leader, especially a leader who holds a position of influence within their organization, with the ability to affect change. On this episode of the Reboot Podcast, Jerry is joined by Nathalie McGrath, VP of People at Coinbase. Having seen the company grow from ten employees to over 250 employees in just four years, with potential to double their numbers by the end of 2018, Nathalie has experienced first hand the “rollercoasty” bumps and dips that innately arise when trying to sustain a company during extended periods of hyper-growth. In her time with Jerry, Nathalie opens up about her own battles with imposter syndrome, the challenge she faces in combating the creeping feelings of burnout, and how she as VP of People, can help support and sustain the members of the Coinbase team who might be struggling with similar sensibilities. As their conversation unfolds, Jerry speaks to the importance of remembrance, whether it’s of fear, or the wish for love, safety, or belonging, and how in recalling those instances, Nathalie and her peers are in a unique position to build a more resilient and humane organization driven by profoundly meaningful leadership. Links #76 - A More Powerful Way of Working - with Patty McCord - https://www.reboot.io/episode/76-powerful-way-working-patty-mccord/ Leave us a review on Itunes! 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. 

For leaders, when our aspirations and passions align, a crucible is formed from which creativity and productivity stem. At this point in our entrepreneurial journeys we might burn a little brighter, and our way forward feels undeniably palpable. Riding the tide, we may begin to feel ourselves cresting the wave and entering a place where the water becomes muddy and our paths unclear. We’ve entered the dip, and suddenly find ourselves in a quit it or stick with it moment where we must determine how we want to walk through this world. On this episode of the Reboot Podcast, Jerry is joined by friend, entrepreneur, author and speaker, Seth Godin. In this conversation, Seth and Jerry seek to tackle the dip, asking us to consider what is actually happening when it occurs, reminding us of the importance of finding our allies during this time, and how living in the tension of unknowing can actually be the catalyst for attuning our understanding to the most authentic way forward – in our companies, our relationships, and on our own personal paths. Links Pema Chodron’s - Comfortable with Uncertainty - https://www.amazon.com/Comfortable-Uncertainty-Cultivating-Fearlessness-Compassion/dp/1590300785 Seth Godin’s - The Dip - https://www.amazon.com/Dip-Little-Book-Teaches-Stick/dp/1591841666 #33 - Do I Event Have a Superpower - with Kent Cavender-Bares - https://www.reboot.io/episode/33-do-you-have-a-superpower/ #73 - Jeff Orlowski - Chasing Purpose: - https://www.reboot.io/episode/73-chasing-purpose-jeff-orlowski/

As leaders, navigating the balance between serving our vision and supporting those who are integral to its success can be a delicate line to walk. When we stand as warriors, with strong backs and open hearts, the seeds of servant leadership are planted. As servant leaders, we create safe, structured containers to bear witness without judgement, allowing for us to build and create meaningful connections. It is in the opening of ourselves to true genuine acts of compassion, that an enhanced sense of resiliency to weather the storms of our lives is nurtured and strengthened. In her second appearance on the Reboot podcast, Roshi Joan Halifax, author of Standing at the Edge: Finding Freedom Where Fear and Courage Meet, works with Jerry to unravel the power of edge states, the importance of taking a compassionate stance in leadership, and how the suppleness that stems from compassion leads to enhanced resiliency and true freedom. Links Standing at the Edge: Finding Freedom Where Fear and Courage Meet #55 - Fierce Compassion - with Roshi Joan Halifax

If your closest colleagues were asked to describe the way in which you conducted yourself in your professional career, what might you hope to hear? For Semil Shah, the adjectives he strives for are: dependable, consistent, and reliable. As the founder of Haystack and the father of three young children, Semil takes immense pride in his ability to be seen as available and accountable despite his busy schedule, so much so, that he feels pangs of guilt when he considers his dependability to be slipping. In his second appearance on the Reboot Podcast, Semil works with Jerry to unpack the driving forces that sit behind his need to be seen by his peers in a certain light, and how this need might be limiting his ability to build honest, meaningful connections with those he cares about. Through their conversation, Jerry and Semil explore the root of Semil’s guilt, the power of perception, and beauty of aging with grace. Links Semil Shah on Twitter - https://twitter.com/semil #46 - Hitting a Wall - with Semil Shah - https://www.reboot.io/episode/46-we-are-not-different-with-semil-shah/

In a modern working world which often venerates the ‘grind,’ - long hours and dogged work-ethic - as the dominating model for focused career development, where does that leave room for building families and raising children? In today’s episode, Jerry is joined by Melissa Pasquale, mother of three and Chief Operating Officer at Engain. Together, Melissa and Jerry consider the navigational challenges of being a parent while maintaining a career. Throughout their conversation, Jerry calls on Melissa to consider the fallacy in yearning for the perfect work-life balance; asking us all to consider that our longing to achieve harmony between work and life inevitably imparts feelings of guilt at our inability to do it all (the notion of, "I'm not really working unless I'm panting.”). When we recognize that we can’t absolve the guilt we feel in that nebulous place of balance between work and life, we can pause to consider the deeper question of, “How we are complicit in the need to be ‘good’ enough - at work, as parents, and in life?”

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” — Author Unknown In a culture driven by a series of actions and reactions, how much consideration do we give to the space that lives in the inbetween? When triggered, what might happen if we allow ourselves to pause and tune into our hearts, dropping into what is holding true for us in that moment? In allowing ourselves that brief period of time between stimulus and response, we can learn how to shift our responses from ones of reflexivity to reflectivity - where the resulting interaction emanates respect and trust for ourselves and others. On this week’s episode of the Reboot Podcast, Nicole Glaros, Partner at Techstars, joins Jerry for a thoughtful conversation on perceived awareness, the power of mindfulness, and the inherent resiliency which arises when we master the ability to widen the gap between stimulus and response. Links Nicole Glaros - https://twitter.com/nglaros Founder Fights - https://www.thecornerboxing.com/founder-fights Reboot Bootcamps - https://www.reboot.io/service/bootcamps/

If you’re an avid listener of the Reboot Podcast then you are well acquainted with podcast host and Reboot CEO, Jerry Colonna. You might know that he has the particular gift of making founders cry, and that he possesses the ability to drive authentic conversations with tenderness and compassion. But what makes Jerry such a great coach, leader and friend? For this episode of the podcast, we’re flipping the script on our host, bringing in long time friend and colleague Brad Feld to anchor a conversation in which Jerry recounts the pieces of his past that have shaped his life and led him to where he is today. Together they discuss a multitude of topics, including the power of journaling, the importance of quietness and listening, and how Jerry’s insatiable curiosity drove his career path from journalist, to venture capitalist and now to author and coach. Links Brad Feld on Twitter - https://twitter.com/bfeld

What is it like to be part of a group of peers, who meet regularly, to discuss your most vulnerable challenges that may or may not be related to your business? What does that interaction do for you and your leadership? How does that affect your organizations? In this episode, Al Doan (founder of Missouri Star Quilt Company), Christine Carrillo (CEO of JOANY), Keeley Tillotson (CEO of Wild Friends Foods), and Bryan Birsic (CEO of Wunder) come together to talk with Jerry Colonna about how important their peer groups have been for their personal and professional lives. They talk about the bonds that form and connections made beyond company size and title to a shared humanity, and the importance of space to speak honestly about fears and concerns and struggles, as well as wins. They also touch on how supportive conversations and deep listening fosters accountability at one’s growth edges, self-discovery, and a practice of vulnerability that ripples out into their companies, families, and friendships at large. And, how through their peer groups, they arrive at better versions of themselves and better leaders in their own organizations. Links Reboot Circles/Peer Groups - http://www.Reboot.io/circles

Radical honesty - an open and authentic contribution, which lacks the intention of causing unnecessary pain and suffering, but serves to provide a mirror in which we can clearly reflect on the aspects of ourselves to which we are blind. On this episode of the Reboot Podcast, Jerry is joined by Patty McCord, former chief talent officer of Netflix, renowned for pioneering the use of radical honesty in the workplace. With her new book, "Powerful: Building a Culture of Freedom and Responsibility", Patty aims to clearly define the best path for creating workplace cultures of high performance and profitability. Jerry and Patty consider how the implementation of radical honesty in our organizations serves to forge solid, supportive spaces where workplace safety is no longer defined solely by the assurance of employment, but contains space for team members to feel seen, heard and nourished to grow, where skill sets are broadened, and diverse people with different ways of thinking come together without fear or expectation to judge or be judged. Wouldn’t that be a more powerful way of working? Links #43 – The Dharma of Inclusivity – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/ Patty MCcord - Powerful - https://www.amazon.com/Powerful-Building-Culture-Freedom-Responsibility/dp/1939714095

Judson Brewer, Director of Research at the University of Massachusetts Medical School Center for Mindfulness, is a revolutionary thought leader in the field of habit change and the “science of self-mastery.” In this discussion, Judson and Jerry ponder identity, how beliefs about our character might shape the way we show up to meet the world, and the ways in which our perceived identities restrict and confine our sense of self. Links UMass Center for Mindfulness - https://www.umassmed.edu/cfm/ The Craving Mind - https://www.amazon.com/Craving-Mind-Cigarettes-Smartphones-Hooked/dp/0300223242

As leaders, what might happen if we attempted to lead from a place of honesty, equanimity, and compassion? Might we transform our organizations and workplaces into safe oases where our fullest selves emerge, allowing ourselves to step into purpose and the meaningful work of our lives? In this conversation, originally aired on The Interdependence Project Podcast hosted by Tarikh Korula, Jerry and Tarikh tackle the question, “How human can we be as leaders?” We’ve decided this would be a great episode to share with you for the holidays, as we wrap up one year and set out into the fresh tracks of another new season. Links The Interdependence Project Podcast - http://theidproject.org/media/Podcast

On this episode of the Reboot Podcast, 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 of the best mediums for effecting positive change, Jeff founded Exposure Labs. Self-described as an ‘impact production company,’ their mission focuses on utilizing visceral, honest storytelling to enact change and enable open conversations on tough subjects. In this conversation, Jeff discusses the parallels of filmmaking and serial entrepreneurship, reflecting on how his new projects can generate the same feelings of uncertainty, thrill, and fear that often arise in early-stage startups. Jeff shares his journey into filmmaking and how he sees himself first and foremost as a problem solver. Together, Jerry and Jeff hold a dialogue on Purpose, pondering its elusiveness, why we chase it and the reasons we often seek our purpose in the ‘wrong’ places.

Matt Tara is the CEO of an e-commerce fashion company that failed, but is still very much alive in his head. As a former venture capitalist in private equity, Matt thought he’d be swift to success as an entrepreneur. When the road turned rocky, Matt was forced to put his company to rest, and he was left with many multifaceted feelings -- among them: failure, grief, and the understanding of what it means when an entrepreneur says “this is hard.” Most of all, he felt abandoned and at a loss for peers who could really listen to him. In this conversation, Jerry helps Matt conceptualize the latest speed bump in his life. They begin to unpack all of the gifts and lessons received from this experience and propose tactics for keeping Matt’s inner critic at bay as he considers what’s next.

Bobby Brannigan, CEO of Mercato, has built his second company into a steadily growing business in a hard market with narrow margins. While the company is growing strong, he longs for the excitement of his first startup - which he remembers as a thrilling success. In this conversation, Jerry asks Bobby to consider what having high-risk stakes means for him, and how he can connect to that sense of confidence and aliveness in other aspects of his life. They also acknowledge that patience and persistence are integral to affecting the change Bobby wants to see in the market he cares about - and how it’s not so easy being patient when you know where you want to get to. Links Mercato - http://www.mercato.com

How can you expect to serve others, whether it be customers, portfolio companies, or your organization if your own house is not in order? In this episode that we originally ran last summer, we welcome Brad Feld and Fred Wilson back to the Reboot Podcast. Jerry, Brad, and Fred have a friendship and history that goes back 20 years, and the wealth of experience between them as entrepreneurs and investors is truly incredible. Fred, Brad, and Jerry share stories from the past, moments where they were pushed to their limits physically and emotionally. They talk about the critical steps they’ve taken to being an effective and supportive board member and investor, and how the lessons from past painful experiences show up in the values of their firms. This episode also launches our very practical skills course - Reboot Your Board - a collection of the wisdom from Fred, Jerry and Brad on how to create, build and maintain the best board possible. Learn more at http://www.RebootYourBoard.com Links Reboot Your Board - http://www.RebootYourBoard.com Brad Feld's blog - https://www.feld.com/ Fred Wilson's blog -http://avc.com/

Erin Frey and Ti Zhao are the co-founders of Kip - an app which aids in locating a quality therapist and helps you measure your progress. In this episode they sit down with Jerry to talk about what makes them tick and how they work together as leaders. This includes emotional literacy and helping each other regulate when tough issues arise. What does your cofounder (or partner) do when they are scared, angry, sad, triggered? Do you know what they need in that moment? Making time to discover the operating instructions for your partner solidifies not only your communication with each other, but also, as Jerry notes, tending to good communication sets culture, direction, and creates the conditions in which raising capital is enhanced. Links Kip - Smarter Therapy - https://www.hellokip.com/ Erin Frey - https://twitter.com/erinfrey Ti Zhao - https://twitter.com/ti_am_i

Jason Jacobs, former founder of Runkeeper, pursued being an entrepreneur with passion and maniacal focus. After starting Runkeeper at age 30, he now finds himself on the other side at 41 post-acquisition, finally reflecting back on the last decade of work. Knowing that he wants to experience building the next company differently, in a more healthy way and with more joy, Jason talks with Jerry about the conundrum of getting lost and consumed in the fire of work. And, how to dive into his work without being so unhappy. At this mid-life juncture of Jason’s time before his “Second Act,” they take the opportunity to pause and unpack deeply held notions about how work must be, what success is, and what it means to lead a fulfilling life. Links "The Problem of the Potter" - https://www.themonsterinyourhead.com/2010/01/31/disappearing-into-the-fire/

Ben Rubin and Dan Harris have found themselves as unlikely cofounders in 10% Happier, which came together when Ben’s company, Change Collective, underwent a successful pivot into a new focus, a new name, and a new co-founder. At the time, Ben stared down his biggest fears of failure - that of creating another “smoking black hole” - only to shift the company, raise money and relaunch the product all in a short two month span, pulling off what their investor Matt Harris called “a triple lindy.” Almost two years later, 10% Happier is among the top mindfulness and guided meditation apps. In this episode, Ben and Dan open up to Jerry about what it’s like being cofounders. They shed light on how their mutual anxieties affect their relationship and their company. Links http://www.10percenthappier.com/Reboot

Adeesh Agarwal is an architect who has worked in real estate, med-tech, and had started and managed his own design firm, which recently closed it’s doors. He finds himself soul searching at 40 years old looking back at the choices he’s made to have a job and be a responsible caretaker for his family. He struggles with finding work that isn’t soul-sucking, that creates safety and opportunity for his family, and wanting to have a sense of stability and sense of progress in his life. As he looks at his life and the choices ahead, he asks: Who am I? What are my strengths? Jerry and Adeesh talk about how there’s a much deeper existential question behind those questions, and how a better question is to ask: What am I made of? And how do the aspects of me come together in ways that I am proud of and ways that hold me back?

Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joined Jerry for our very first podcast episode in 2014 to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended the first CEO bootcamp and began to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge that could have destroyed his business. In this conversation, Jerry and Derek talk about how in our challenges at work lies a conversation about what impacted who we are and how we relate to life, work, and money. Derek’s openness and introspection may inspire you to re-examine how your own stories, upbringing and past experiences are impacting your business and your life. Links Greatist - https://greatist.com/ Twitter - https://twitter.com/derekflanz - https://twitter.com/greatist

Nancy Lublin, CEO of Crisis Text Line, a non-profit that provides free 24/7 support at your fingertips, is a successful serial social entrepreneur. Previously at Dress for Success and Do Something, her journey as a CEO has been one towards a more authentic and human style of leadership. This journey has informed how she see’s her product and the companies she runs. In this candid conversation with Jerry Colonna, Nancy talks about what it means to be a social entrepreneur and being human centric in this world of chat bots, numbers, OKRs and KPIs. Links Crisis Text Line - http://www.crisistextline.org/ Nancy Lublin on Twitter - https://twitter.com/nancylublin

Throughout his life Adi Mashiach has been a brilliant student, a successful doctor, and has experienced two successful company exits. Along with his wife Mirella, Adi has stepped into the world of VC with the creation of Mesia Ventures. Having just moved to the United States less than a year ago with his family, Adi has started to feel the familiar pangs of belonging trying to break into new circles and begin building a new venture fund. Recently, Adi has begun to wonder how to live his passion for helping others, and how to fit in without losing himself in the fire (something he’s experienced twice before in his life). In this episode, Jerry Colonna and Adi discuss how our intellect can help us figure out only so much in life, and how listening closely to our heart can reconnect us with the forgotten parts of ourselves that, once reclaimed, can sit beside us as we endeavor through life. Links Love after Love by Derek Walcott - https://onbeing.org/blog/love-after-love

In an entrepreneurial world where being a billionaire is a yardstick for self-worth, and unattainable goals can give us a false sense of responsibility, control and drive, what is the collateral damage to ourselves? As we chase a sense of perfectionism, and measure ourselves against big goals, how do we counteract the sense of self-loathing we can impinge upon ourselves when we fall short of the images we’re up holding? In this conversation, Jerry sits down with Sharon Salzberg, on her new book "Real Love: The Art of Mindful Connection" to discuss the ways in which love might be a counter-intuitive antidote to the ups and downs of entrepreneurship. We learn that as we cultivate a sense of love and compassion for ourselves in our ambitious pursuits and adventures in life, we bolster our resiliency to face life as it is. Links "Real Love: The Art of Mindful Connection" by Sharon Salzberg - https://www.amazon.com/Real-Love-Art-Mindful-Connection/dp/1250076501 Sharon Salzberg on Twitter - https://twitter.com/SharonSalzberg #22 – Does Anyone Really Know What They Are Doing? – with Sharon Salzberg - https://www.reboot.io/episode/does-anyone-really-know-what-they-are-doing/

Sally Spencer-Thomas is a psychologist who found herself in a moment in which she was not prepared when her brother died of suicide. After that significant event in her life, Sally poured much of her life into engaging leaders and finding bold, gap-filling solutions for suicide prevention in schools, workplaces, and communities. Driven by the memory of her brother, Sally dove into her work, and along the way, she found a community and purpose around her brother’s legacy. Over the last 14 years, Sally encountered her own onerous moments of depression. From these moments, she came to understand the power of community and the importance of a caring person. On her journey, Sally has become more attuned to asking, “What is this moment teaching me? What can I do to learn here?” a testament to her resilience. Now, she’s facing big life transitions in both her work and her role as a parent, and she finds herself listening for what her inner voice is saying as she’s wondering, “Who am I, now, in this season of my life?”

Khe Hy spent 14 years in Financial Services and was successful by all signs, but his work and life felt ‘meh.’ Something felt disconnected from him as he suited up in the morning and turned off the finance switch in the evening. He opted for a life of more meaning, and started RadReads, a passion project now grown into a community of sorts. But something still didn’t feel right for Khe. Even though he preached a lot about what’s important, he found that a hard talk to walk and instead found himself putting the most important things in his life - his wife and daughter - last on his list of priorities. Despite all of Khe’s efforts in meditation, mindfulness and reflection, he struggled to figure out how to be present for his life. Instead he found himself thinking about ideas, people in his network, and ways to improve. As a self-proclaimed life-hacker, he struggled to find the metrics and hacks to be present. As Khe and Jerry discuss, perhaps the answer to being present is deeper than hacks and metrics. Perhaps the clue lies in what he’s so afraid of. Links RadReads - https://radreads.co/ Khe Hy on Twitter - https://twitter.com/khemaridh

Al Doan led his family’s fledgling small town quilting shop to a leading online retailer with over 450 employees in just a few short years. To the outside world, this rapid growth established Al has a wildly successful and admired leader, but behind closed doors Al was struggling. He found himself behaving in ways contradictory to his character and struggling to feel happy and content. Sure, he was killing it as an online quilting retailer, but was this really what he wanted his life to be? Recognizing things were not working, he reached out for help from a trusted friend and advisor. This friend connected Al with Jerry, leading to a new journey of self-inquiry and discovery for Al. A journey that has ultimately led him to walk through the fear and challenge of stepping down as CEO, to create the space for the life of his dreams to emerge. Links Missouri Quilt Company - https://www.missouriquiltco.com/ Al Doan on Twitter - https://twitter.com/drbillnye Signs you need to leave your startup - https://goo.gl/Q0YmtO CEO bootcamp - https://www.reboot.io/service/bootcamps/ Reboot Circles - https://www.reboot.io/service/peer-groups/ Episode #29 Who’s in your corner? With Carrie Barry - https://www.reboot.io/episode/29-whos-in-your-corner-with-carrie-barry/

Simon Cant’s path to becoming a VC has been a windy road. Building on a career that includes stints as a lawyer, founder, consultant, director of a non-profit and advisor, he is now an LP in Reinventure, an Australian fintech fund. Alongside his meandering career path, Simon has battled to slow the swing between a strong desire to exert control and an acute awareness of his own need to surrender. In this conversation Jerry leads Simon to remember that there is no such thing as a perfect surrender. Instead, surrender is a lifelong practice. Links Grace, VC and Surrender - https://hackernoon.com/grace-vc-and-surrender-4475a6c1e325#.hqn5apr6h Simon Cant on Twitter - https://twitter.com/simoncant

“If we have no peace, it is because we have forgotten that we belong to each other.” - Mother Teresa For Bijan Sabet- an investor, US citizen by birth and descendant of Korean and Iranian immigrants- the January 27th Trump administration issue of an executive order banning the entry of residents and refugees from a number of Muslim countries deeply disturbed him for a number of reasons. Recalling his own early experience of being othered as the child of an Iranian immigrant during the Iran Hostage Crisis of the late 70s, his heart broke that other. Driven to mobilize his heart ache to action the best way he knew how, he launched a fund matching campaign for the ACLU. Bijan’s initial expectations of a several month timeline to raise the funds were blown away when the campaign received overwhelming support and reached its goal (and beyond) in less than 3 days. In this conversation, Jerry and Bijan discuss the experience of feeling othered and how that changes what it feels like to belong. The shame and embarrassment of feeling different or outside, and the healing that occurs when we find ourselves on the other side- feeling a part of and knowing we are not alone anymore. Links Bijan Sibet on Twitter - https://twitter.com/bijan "Not Alone Anymore" - https://goo.gl/HXRgxH Episode #20 Investors Are Human Too - https://www.reboot.io/episode/investors-are-human-too/ Episode #19 Building a House of Belonging - https://www.reboot.io/episode/building-a-house-of-belonging Stickball - https://en.wikipedia.org/wiki/Stickball

But little by little, as you left their voices behind, the stars began to burn through the sheets of clouds, and there was a new voice which you slowly recognized as your own, that kept you company as you strode deeper and deeper into the world, determined to do the only thing you could do-- determined to save the only life you could save. - Mary Oliver, The Journey John Guydon first appeared on the podcast in Episode #41: Are You Afraid of Your Own Power. It has been just under a year since that episode and a lot has changed for John. The company he discussed on that episode, Lassy Project, has come to close and he is diving head first into two new projects-- a documentary film and a new company, Master The Book. As in the last episode, John’s exuberance for these new endeavors is palpable, but in this discussion he and Jerry notice a fear underneath the charisma. In this episode Jerry and John build on the idea of embracing your super power, discuss the fear in being labeled, and how John’s purpose continues to undergird all he does. Links John Guydon on Twitter is @IamJohnGuydon - https://twitter.com/IamJohnGuydon The Dark Dollar - http://thedarkdollar.com #41 – Are you afraid of your own power? – with John Guydon - https://www.reboot.io/episode/41-afraid-of-your-own-power-john-guydon/ Master the Book - http://www.masterthebook.com #43 – The Dharma of Inclusivity – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/

"To pay attention, this is our endless and proper work." - Mary Oliver In this episode Jerry Colonna is joined by Roshi Joan Halifax, a Buddhist teacher, Zen teacher and anthropologist. Jerry first met Roshi Joan a few years ago when she was presenting on her G.R.A.C.E. model, a process for cultivating compassion in leaders and applicable to anyone looking to cultivate practicing compassion in their lives. Throughout the episode Jerry and Roshi Joan discuss how leaders can learn to best allocate their attention, the pitfalls of pathological altruism, and how practicing compassion is the cornerstone to wise leadership. Links Roshi Joan Halifax on Twitter - https://twitter.com/jhalifax Upaya Zen Center - https://www.upaya.org When Things Fall Apart - http://a.co/edOQ1a7

A disciple asks the rebbe: “Why does Torah tell us to ‘place these words upon your hearts’? Why does it not tell us to place these holy words in our hearts?” The rebbe answers: “It is because as we are, our hearts are closed, and we cannot place the holy words in our hearts. So we place them on top of our hearts. And there they stay until, one day, the heart breaks and the words fall in.” - Hasidic Tale, as told by Parker Palmer Every entrepreneur hears the call of an inner voice. We may call it drive, intuition, or our guiding voice. Regardless of name it pushes us forward. This voice can be our most powerful ally in the pursuit of authentic leadership, or become our greatest enemy when clouded by fear, anxiety, or self-judgment. Most of us equate struggle as a bad or wasted experience. But as we find in this episode, that association is far from the truth. Instead, heartbreak holds our greatest potential to allow true transformation to be possible. Fresh off an $8M round, Matt Munson led his team at Twenty20, a crowd-sourced commercial photography catalogue, in a radical pivot--changing the business model from B2C to B2B. The business seemed to be moving in the right direction, yet Matt began to feel crippling pressure to achieve more growth. This pressure, perhaps better defined as anxiety, quickly became all consuming, permeating through the entire Twenty20 team. It wasn’t long until the company had reached another tipping point to survive. With the support of his board, Matt made the difficult decision to layoff nearly 80% of his staff and embrace a new path-- one centered around simplicity, transparency, and embracing the open-hearted warrior within. Links Matt Munson on Twitter - https://twitter.com/mattmuns Twenty20 on Twitter - https://twitter.com/Twenty20app Twenty20 - https://www.twenty20.com How I burned 10 Million Dollars so you don’t have to - https://goo.gl/MIpPbW Getting Real - https://gettingreal.io

Almost all successful entrepreneurs will fail - if not fail, fail, fail, and fail again - on their path to success. Every human being made choices in their lives which they regret, are embarrassed of and have caused them deep shame. What would your life be like if you were known only by the worst thing you had ever done? Catherine Hoke is the founder of Defy Ventures, a program that helps incarcerated individuals transform their hustle to entrepreneurial ventures. Following a chance visit (as a guest) to a prison at the age of 26, Catherine left behind a successful investment career to launch a program to build on what she recognized were valuable entrepreneurial skills - simply applied to illegal businesses. Through the journey of building two wildly successful organizations, Cat had her own personal experience of failure, great shame and having to grant herself grace, and a second chance. Nestled in this conversation about failure, mercy and second chances, is an important second discussion. Joined by investor Brad Feld, this episode also includes a heartfelt reflection on the lottery of birth, acknowledging our own privilege, and what we can do when confronted with these realizations. Links Cat Hoke on Twitter - https://twitter.com/Catherine_Hoke Defy Ventures on Twitter - https://twitter.com/DefyVentures Brad Feld on Twitter - https://twitter.com/bfeld Understanding Privilege – My Experience in Prison - http://feld.com/archives/2016/11/understanding-privilege-experience-prison.html Feld Thoughts - http://feld.com Defy Ventures - https://defyventures.org This former drug dealer is now running a successful gym - https://www.facebook.com/NowThisNews/videos/1127697567320366/ Defy Ventures is helping inmates transform their hustle. - https://www.youtube.com/watch?v=lLoacd_rJsY Episode #43 – The Dharma of Inclusivity – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/

“If we hope to go anywhere or develop ourselves in any way, we can only step from where we are standing. If we don't really know where we are standing... We may only go in circles...” ― John Kabat-Zinn The Reboot podcast was started because we believed that there needed to be an authentic, real conversation about the emotional journey of entrepreneurship. One that included its valleys and not just its peaks. One in three entrepreneurs will struggle with depression or burnout in their career, yet when it happens to them, many entrepreneurs feel totally alone in their experience. Rob Symington is a founder and entrepreneur who experienced a debilitating period of burnout following the launch of his startup, a startup that was inspired by the idea that work could be more fulfilling, less stressful and generally improve people’s lives no less. In this conversation, Jerry and Rob discuss his experience, why Rob believes it’s so important for him to share it, how he is moving forward, and the fact that the pressure of doing something you passionately believe in can challenge you unlike anything else. Links Escape the City - http://www.escapethecity.org "Email to team on my startup burnout, lessons learned, & finding a new way forwards" - goo.gl/A7vW2w Elle Harrison - http://www.wildcourage.com "It’s not you, it’s the startup life" - https://medium.com/reboot-leadership-resiliency/its-not-you-it-s-the-startup-life-9290a5183ee9#.kenj6fbw0 "How to avoid burnout" - https://medium.com/reboot-leadership-resiliency/how-to-avoid-burnout-9690601852d8#.syts nzk4h "Love After Love" by Derek Walcott - https://allpoetry.com/Love-After-Love

“One does not become enlightened by imagining figures of light, but by making the darkness conscious. The latter procedure, however, is disagreeable and therefore not popular.” - C.G. Jung Exploring one’s shadow is no easy undertaking. The idea of getting to know what Jung referred to as, “That which I do not wish to be” is rarely considered an exciting prospect. Yet we implore all leaders to be courageous and get to know and learn to work with their shadow. It is only when we do the work to make the unconscious conscious, that we are able to build true compassion for ourselves and others; freeing us to become the leaders we were born to become. James Hollis is a Jungian analyst, author and lecturer whose work has inspired and influenced us at Reboot. In this episode Jerry and James talk in depth about the Jungian concept of shadow, how shadow shows up in leadership, and what we can do once we become aware of our shadow. Links James Hollis’s website - http://www.jameshollis.net "Why Good People Do Bad Things" - goo.gl/cS6kWe Episode #14 Shadow and Leadership - https://www.reboot.io/episode/shadow-and-leadership/ Episode #28 Reclaiming Shadow - https://www.reboot.io/episode/28-reclaiming-the-shadow/ Episode #42 Building Relational Trust - https://www.reboot.io/episode/42-building-relational-trust-parker-palmer

This is the bright home in which I live, this is where I ask my friends to come, this is where I want to love all the things it has taken me so long to learn to love. - David Whyte, from "The House of Belonging" Virginia Bauman and Iris Bainum-Houle have experienced great success- Virginia as an entrepreneur and founder, Iris as a designer for film and entertainment- and both have also experienced great feelings of otherness. While successful, both felt a call to live and work differently, a call that arose out of the desire to be their full authentic self at all times. This new connection led them to take their own experiences of otherness and transform them to create a sense of belonging, love, acceptance, and community for others. Links Cuties - http://hicuties.com/about/ "The Dharma of Inclusivity" – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/

Are you courageous enough to look in your blind spots? Alex Blumberg is at a crossroads. His company, Gimlet Media, is producing some of the most successful, interesting podcasts out there with household names such as Reply All, Heavyweight and Startup Podcast. Alex has been working with Jerry as his coach for a while now and has just completed his first 360 Review. In this raw, vulnerable, and courageous episode-- a cross post of Startup Podcast Season 4, Episode 3-- Alex wrestles with the information that is illuminated in his 360 Review. Are they shortcomings to be tucked back under the rug? Or are they opportunities for growth and a deeper understanding of himself as a leader and human? Links Startup Podcast https://gimletmedia.com/show/startup/ Gimlet Media https://gimletmedia.com Alex Blumberg https://twitter.com/abexlumberg

360 reviews are a tool that can help leaders make course corrections, supporting both individual growth and the growth of the company. They are an opportunity to hear specifically through the voices of their colleagues how their behavior is making an impact. In this Reboot Extra, Jerry and VC Fred Wilson talk about the importance of 360 reviews, what a well executed 360 review can do for the board-CEO relationship, as well as some suggestions from Fred for CEOs to get the most out of the review process. Links Reboot 360 Reviews - http://www.Reboot.io/360

“I want to think again of dangerous and noble things. I want to be light and frolicsome. I want to be improbable beautiful and afraid of nothing, as though I had wings.” ― Mary Oliver, Owls and Other Fantasies: Poems and Essays Startups are founded with outcome in mind--creating needed change in the world, a successful exit, or most commonly, both. Holding our desired outcomes, or endings, builds the drive for our best work. But when things don’t unfold along the lines or on the trajectory we desire, it can be easy to generalize the entirety of our efforts as a failure. Tarikh Korula has founded a number of companies but has yet to achieve an exit. In this episode Jerry and Tarikh discuss how we define failure and how we hold the tragic gap--the space between where we do the work and our often elusive end aspirations. Links Tarikh Korula on Twitter - https://twitter.com/tarikh Robert Irwin: Why Art? - https://youtu.be/5Ac-m3W9fGY "Farewell to Katch" - goo.gl/rx4O1s Parker Palmer on Standing in the Tragic Gap - http://www.couragerenewal.org/723/

“Development involves giving up a smaller story in order to wake up to a larger story.” - Jean Houston When is the moment at which you become an entrepreneur? Is there a definitive moment or action that makes it official? Sarah Weiler followed her passion to bring creativity and playfulness into the workplace by founding The Power of Uke. Like many entrepreneurs, Sarah is still working a day job to pay her bills as she builds her business. The Power of Uke is growing,­­ gaining clients and billings, but Sarah is reluctant to identify as an entrepreneur. In this conversation Jerry and Sarah discuss what’s holding her back from identifying as an entrepreneur and why it’s so hard to shift from living to satisfy what you think is expected of you to what you want and love to do. Links Sarah on Twitter ­ - https://twitter.com/weilersarah Power of Uke on Twitter - https://twitter.com/powerofuke ­ Power of Uke - http://powerofuke.com/

“I am not what has happened to me, I am what I choose to become.” - Carl Jung Amir Salihefendic, the founder and CEO of Doist, is the creator of the powerful and popular productivity tool, Todoist (which is awesome). He comes to Jerry feeling torn between two seemingly different directions for his business. On one side, he feels the ambition to do big, world changing things and to be on every smartphone and desktop. But on the other side, as the son of entrepreneurial parents who owned a grocery store, he knows how important it is to just keep the business alive and take care of yourself and your family (and to be grateful for that) - to not put your family, your health, yourself at risk. The ambitious path with burnout or the steady, safe path with possible regrets? He has wrestled with this as something he must decide, but what if there isn't a choice? Or what if there is a 3rd option he’s not seeing? Jerry and Amir explore this apparent conflict, talk about his upbringing and his family’s escape from the war in Bosnia when he was young, and in this exploration they uncover a new path forward for Amir and the business, one of integration. Links Amir Salihefendic on Twitter - https://twitter.com/amix3k Doist - https://doist.com/ Todoist - https://todoist.com/ Todoist on Twitter - https://twitter.com/Todoist Reboot.io Podcast # 7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin - https://www.reboot.io/episode/depression-and-entrepreneurship/ Parker Palmer - http://www.couragerenewal.org/parker/

A few weeks ago, we released our first Reboot Extras in collaboration with NextView Venture’s Traction Podcast. Today we’re happy to bring you part 2 of that conversation. In today’s Reboot Extras, NextView’s Jay Acunzo really takes on the role of a skeptic (and plays it quite well). He challenges Dan with a question that we sometimes hear from founders and startup leaders: “Does the soft, interpersonal and relational stuff really matter?” Or the more common form of pushback: “yes, yes, I know I should think about that stuff - but I’ll do that when we’re further along and I have more time.” It’s the idea that if I’m not seeing a measurable impact on my bottom line RIGHT NOW by investing in the health of my team and co-founder relationship, then how can it possibly be worth my time? [Spoiler: The best time to do this type of work? Now.] We also explore several big challenges facing founders in an effort to debunk the myth that the “soft stuff” is less important than the “harder” skills we typically hear more about. We believe the startup world needs less “how tos” and more self-reflection around the question: “how am I personally showing up?” And this is perhaps the most important question startup founders can ask themselves - after all, one of the biggest reasons startups fail is due to Co-Founder conflict. Subscribe to the NextView blog (and podcast): - http://www.nextviewvc.com/blog Sign up for the Reboot.io Podcast and more - http://www.reboot.io/signup Follow Dan and Jay on Twitter: - http://www.twitter.com/jayacunzo - http://www.twitter.com/danputt

“Most of us have two lives. The life we live, and the unlived life within us. Between the two stands Resistance.” ― Steven Pressfield "The War of Art" Semil Shah has done remarkably well as a one-man shop, but he is wrestling with the challenges of growing his business and being with his growing family of 5, while continuing to grow himself. Adding to those challenges, there’s also a sneaky voice for him, one that can drive him and also hold him back, one that is saying to him: “You don’t belong here, yet.” At the end of the day, we are not that different because we all have a version of that voice, often referred to as impostor syndrome, but the opportunity for all of us lies in how we are with that voice. Jerry and Semil explore that voice, and how shifting his relationship with it can help him be a better man and a better investor - the very things it and he are after. Links Full show notes: - https://www.reboot.io/episode/46-we-are-not-different-with-semil-shah/ Semil Shah on Twitter - https://twitter.com/semil Semil Shah's blog - http://blog.semilshah.com/ Getting Things Done by David Allen - https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280 Writing Therapy in Impostor Syndrome - https://en.wikipedia.org/wiki/Impostor_syndrome#Therapy Impostor Syndrome - https://en.wikipedia.org/wiki/Impostor_syndrome Fred Wilson - https://twitter.com/fredwilson

This is our first Reboot Extra bringing you more Reboot content, ideas, and stories from more Reboot Voices. What happens when you and your co-founder experience conflict or strife but don't address it up front? When something festers and is ready to boil over, how do you bring it back down to a good place? This is Part 1 in a series about the ups and downs of being an entrepreneur in a special collaboration with NextView Venture’s podcast: Traction. Specifically, we'll tackle issues of communication, leadership, and mental well-being. Dan Putt of Reboot joins NextView's VP of platform Jay Acunzo for this series. Subscribe to the NextView blog (and podcast): - http://www.nextviewvc.com/blog Sign up for Reboot Podcast and more - http://www.reboot.io/signup Follow the guys on Twitter: - http://www.twitter.com/jayacunzo - http://www.twitter.com/danputt

"Wisdom, then, is a deeper way of knowing. Wisdom is the art of living in rhythm with your soul, your life, and the divine. Wisdom is the way that you learn to decipher the unknown; and the unknown is our closest companion. So wisdom is the art of being courageous and generous with the unknown, of being able to decipher and recognize its treasures." - John O'Donohue from "Anam Cara: A Book of Celtic Wisdom" We are so fortunate to welcome Brad Feld and Fred Wilson back to the Reboot Podcast. Jerry, Brad, and Fred have a friendship and history that goes back 20 years, and the wealth of experience between them is truly incredible. In what we hope will be a series of conversations, Fred, Brad, and Jerry share stories from the past, moments where they were pushed to their limits physically and emotionally. They talk about the critical steps they've taken to being an effective and supportive board member and investor, and how the lessons from past painful experiences show up in the values of their firms. We’d love to hear your thoughts on this episode, so please check out the show notes at reboot.io/podcast Links Full show notes: https://www.reboot.io/episode/45-whats-love-got-to-do-with-it-fred-wilson-brad-feld Jerry's post on this episode. https://www.reboot.io/whats-love-got/ Fred's first episode of Reboot Podcast https://www.reboot.io/episode/investing-in-trust/ Brad's first episode of Reboot Podcast https://www.reboot.io/episode/live-beyond-compare/ Fred Wilson on Twitter ­ - https://twitter.com/fredwilson Fred’s Blog - http://avc.com Union Square Ventures ­ - https://www.usv.com/ Brad Feld on Twitter ­ - https://twitter.com/bfeld Brad’s Blog ­"Feld Thoughts" ­ - http://www.feld.com/ Foundry Group - http://www.foundrygroup.com/

"Our capacity to fail is essential to what we are." Costica Bradatan http://opinionator.blogs.nytimes.com/2013/12/15/in-praise-of-failure/ Startups fail. We hear it all the time. Failure is good. We hear that all the time too. But we rarely hear about the pain, the shame, and second guessing. And even worse, we rarely hear about what opportunities may lie for our own growth in something ending beyond the pivot and lessons learned. A startup failing is not proof that something is broken within you. In fact it’s an opening and opportunity to find something new within you and for you. Nick Russell was co-founder and CEO of UK based We are Pop-up. Nick joined Jerry on the very day he handed over the keys and closed up shop on his startup of 3+ years. In this discussion, Jerry and Nick talk about what he’s experiencing now, what he learned and wishes he had done differently, and a surprising path forward for him. It's a path that could be helpful for you in your own transitions. For show notes and Nick’s email address go to reboot.io/podcast Links Nicholas Russell on Twitter - https://twitter.com/bettercity We Are Pop Up - https://www.wearepopup.com/ We Are Pop Up on Twitter - https://twitter.com/wearepopup "Let Your Life Speak" by Parker Palmer - https://www.amazon.com/Let-Your-Life-Speak-Listening/dp/0787947350 Pema Chodron - https://en.wikipedia.org/wiki/Pema_Ch%C3%B6dr%C3%B6n

There is real suffering out there, suffering that is causing violence. What are some of the causes of the suffering and how might we address those? It's a true honor to welcome entrepreneur, creator, and educator Konda Mason to the podcast for an important and timely conversation with Jerry. This discussion was recorded last week, and we thought it was really important to get this out sooner rather than later, particularly given the events in Orlando. Konda and Jerry address some of the source causes of this suffering, this pain, and what opportunities might lie in remembering we’re all in this together. This conversation will challenge you on your privileges and inspire you find new ways of connecting with people from all backgrounds. Links The Whole Person Economy - http://www.thewholepersoneconomy.com/konda-mason/ Konda Mason on Twitter - https://twitter.com/swamikondananda Impact Hub Oakland - https://oakland.impacthub.net Spirit Rock Meditation Center - https://www.spiritrock.org/instructordetails?calendarinstructorid=54375

Parker Palmer is a man whose teachings mean so much to us and our work at Reboot, so it's wonderful to welcome him back to the podcast for a new conversation with Jerry. Jerry invited Parker back to explore some important questions: - What is the role of community in responding to a toxic environment? - How do I respond when my leader hasn't done their work and is leading from that place of shadow? - What does it mean when a leader is using organization to resolve unconscious issues? As is always the case when Parker and Jerry get together, this is a conversation packed full of deep lessons on leadership, the shadow, the importance of relational trust, and the incredible power present in community. This episode will leave you with new profound questions and answers about yourself, your role in your organization, and the power you hold, but may not yet accept. Links Parker Palmer - http://www.couragerenewal.org/parker/ "To Bless the Space Between Us" by John O’Donohue - http://www.amazon.com/Bless-Space-Between-Us-Blessings/dp/0385522274 Nelson Mandela - https://en.wikipedia.org/wiki/Nelson_Mandela Rosa Parks - https://en.wikipedia.org/wiki/Rosa_Parks "A Ritual to Read to Each Other" by William Stafford - http://williamstafford.org/spoems/pages/ritual.html

"As we let our own light shine, we unconsciously give others permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.” - Marianne Williamson "A Return to Love: Reflections on the Principles of a Course in Miracles” John Guydon is an entrepreneur and speaker who owns his power more than most. He shares with Jerry his story and how he can’t help but tackle big problems like finding missing children and directly discussing and addressing the economic gap that exists between Black Americans and other communities. Links John Guydon on Twitter ­ - https://twitter.com/Guydon The Lassy Project - http://www.thelassyproject.com/ The Dark Dollar - http://www.imdb.com/title/tt5555176/

“The way to start would be, first, when we feel the tendency to blame, to try to get in touch with what it feels like to be holding on to ourselves so tightly. What does it feel like to blame? How does it feel to reject? What does it feel like to hate? What does it feel like to be righteously indignant?” - Pema Chodron There’s something calming about finding a target for our blame. It’s like in this moment of being lost in a rough sea of chaos and uncertainty, a person to assign the fault is like an unsinkable lifeboat to grasp. We climb aboard, take a deep breath, and relax. We do this as individuals, we do this in organizations, we do this as a society. But what incredibly valuable opportunities lie in resisting the urge to assign blame? What might we learn in what didn’t (or did) work if we explore a bit more? Jerry is joined today by author and CTO Dave Zwieback to talk about just that. Dave, in his book “Beyond Blame,” explores the fallacy of blame, how it fails to identify the immense complexity and interdependency of the world around us, and the real cost of rapidly assigning fault. If we pause and explore, we may just find that blame often prevents us from doing the very thing we want most - to learn and to grow. Links Dave Zwieback on Twitter - https://twitter.com/mindweather Beyond Blame by Dave Zwieback - http://www.amazon.com/Beyond-Blame-Learning-Failure-Success/dp/1491906413 The Five Dysfunctions of a Team by Patrick Lencioni - http://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756 Daniel Kahneman - https://en.wikipedia.org/wiki/Daniel_Kahneman John Allspaw - https://twitter.com/allspaw Truth and Reconciliation Movement - https://en.wikipedia.org/wiki/Truth_and_reconciliation_commission#The_South_African_TRC_and_after

You do not have to be a fire for every mountain blocking you. you could be a water and soft river your way to freedom too. - options by Nayyirah Waheed Mary Lemmer shares the emotional story of seemingly everything working against her in last 18 months - her body giving in, her relationship ending, her business coming apart, and losing her Dad’s approval. These are physically and emotionally painful experiences, and yet what if they are exactly what she needs? What if she was only waiting for this moment to arise? Links The show notes: https://www.reboot.io/episode/39-time-new-choices-mary-lemmer/ Marry Lemmer on Twitter - https://twitter.com/me_lem Foodscape - http://www.myfoodscape.com/ Animas Valley Institute - http://www.animas.org/ Let Your Life Speak by Parker Palmer - http://www.amazon.com/Let-Your-Life-Speak-Listening/dp/0787947350 Pema Chodron - https://en.wikipedia.org/wiki/Pema_Ch%C3%B6dr%C3%B6n Loving-Kindness by Sharon Salzberg - http://www.amazon.com/Lovingkindness-Revolutionary-Happiness-Shambhala-Classics/dp/157062903X

“Hurrying and delaying are alike ways of trying to resist the present.” - Alan Watts What’s the conversation you are having with yourself right now? Maybe you’re thinking about an email you wrote earlier, or need to write later. Maybe you’re thinking about an ever-growing todo list, and feeling the anxiety well up within. Or maybe you are doing all of the above. When you stop to really notice, it’s amazing how many conversations we are having internally at any given time. The most important conversation we have is with ourselves. What are you saying right now? Congressman Tim Ryan is our guest for Episode 38 of the Reboot Podcast. Tim is a special guy, and not just because he’s a congressman, and not just because he’s from Ohio - though that's pretty great too - but because he’s committed to bringing heart, humanity, mindfulness and a long term focus into a space that doesn’t always welcome it: government. In this conversation (originally recorded in November), Tim shares his journey to mindfulness, his ongoing practice in noticing his own inner conversation, and his commitment to mindfully planting seeds for the future and having the patience to watching them grow. Links Sharon Salzberg - http://www.sharonsalzberg.com/ "A Mindful Nation" by Tim Ryan - http://www.amazon.com/Mindful-Nation-Practice-Performance-Recapture/dp/1401939309 Jon Kabat-Zinn - https://en.wikipedia.org/wiki/Jon_Kabat-Zinn "Coming to Our Senses" by Jon Kabat-Zinn - http://www.amazon.com/Coming-Our-Senses-Ourselves-Mindfulness/dp/0786886544 "Full Catastrophe Living" by Jon Kabat-Zinn - http://www.amazon.com/Full-Catastrophe-Living-Revised-Edition/dp/0345536932 "Wherever You Are, There You Go" by Jon Kabat-Zinn - http://www.amazon.com/Wherever-You-Go-There-Are/dp/1401307787 Deepak Chopra - https://en.wikipedia.org/wiki/Deepak_Chopra Wayne Dyer - https://en.wikipedia.org/wiki/Wayne_Dyer Parker Palmer - https://en.wikipedia.org/wiki/Parker_Palmer

"A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves." ­ - Lao Tzu For leaders the temptation to tell, fix, and even do is so strong. “I know the way,” or “I have the answers,” or “the buck stops with me.” Sometimes it’s impossible to resist the ego boost of providing the answer, giving the fix, telling the way. But what impact does this have on the team, and ourselves? And is it even true? Jerry is joined today by Patrick Campbell, co­founder and CEO of Price Intelligently - a bootstrapped company in Boston. Patrick and Jerry explore different leadership styles, the power of “if I die docs,” and how the secret to leadership may not lie in having the right answers, but instead asking the right questions. Links Price Intelligently - http://www.priceintelligently.com/ Price Intelligently on Twitter ­ - https://twitter.com/priceintel Patrick Campbell on Twitter ­ - https://twitter.com/Patticus

Do you love yourself enough to listen with the ears of your heart to the other voices of yourself speaking? - Beno Kennedy In today’s special episode Jerry Colonna, Jim Marsden, and Jade Sherer talk about the power and opportunity of time on the land, Jerry’s own experience on a quest, which was guided by Jim and Jade, and why a quest could change your awareness forever. If it terrifies you, you are ready...go apply at reboot.io/quest. Links Apply for the Reboot Quest - http://www.reboot.io/quest Jim Marsden on Twitter - https://twitter.com/jamarsden Jade Sherer - http://www.earthsecho.com/htm/about.htm Earth’s Echo Explorations - http://www.earthsecho.com/index.htm Animas Valley Soulcraft Program - http://www.animas.org/ Bill Plotkin - http://www.animas.org/about-us/our-founder/ "Soulcraft" by Bill Plotkin - http://www.amazon.com/Soulcraft-Crossing-Mysteries-Nature-Psyche/dp/1577314220

“By cultivating skillful attitudes of mind, we will respond to more and more of life with awareness and wisdom. With steady awareness of the way things are, the perseverance to stay with that awareness, and the willingness to learn from it, we maximize our sense of well-being.” — Steve Armstrong Life happens. It’s full of moments, good and bad, we never thought would happen to us. The magic and opportunity lies in what you do with those moments. Everything is workable if we choose to work with it. And if we choose to let it work us. Our guest today, Richard Hughes-Jones, is choosing to work with it. As a former management consultant, he was always a man with a plan both for himself and others. So it was quite a big leap for him to dive into the entrepreneurial world nearly two years ago, a place where a plan doesn’t guarantee survival. Instead, he was quickly reminded he was part of a bigger struggle, one where plans most certainly do not ensure success or survival: life. In this conversation with Jerry, Richard discusses his battle with cancer, the beauty of uncertainty, and the opportunity for all of us. Links Richard Hughes-Jones Website http://www.richardhughesjones.co/ Richard Hughes-Jones on Twitter https://twitter.com/rhughesjones Parker Palmer - "A Hidden Wholeness" http://www.amazon.com/Hidden-Wholeness-Journey-Toward-Undivided/dp/0470453761 Pema Chodron - "Comfortable with Uncertainty" http://www.amazon.com/Comfortable-Uncertainty-Cultivating-Fearlessness-Compassion/dp/1590300785

“Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakens.” – Carl Jung. "Work is difficulty and drama, a high-stakes game in which our identity, our self-esteem, and our ability to provide are mixed inside us in a volatile, sometimes explosive ways.” That's David Whyte in his incredible book, "Crossing the Unknown Sea: Work as a Pilgrimage of Identity". That volatile, explosive mix is a gift. It presents a tremendous opportunity for us to do our own work, our inner work, and further develop our own understanding of self. In our conversation today, Jerry is joined by Henry May, founder and CEO of CoSchool, based in Columbia. Henry comes to Jerry with this very issue: How might the journey of entrepreneurship, specifically his own, open up new opportunities for him to grow? Or said more directly: How might he use his work at Coschool to do the real work on his humanity? CoSchool - http://coschool.co/ CoSchool on Twitter - https://twitter.com/coschool Teach First UK - https://www.teachfirst.org.uk/ Teach for America - https://www.teachforamerica.org/ Unreasonable Institute - http://unreasonableinstitute.org/ Parker Palmer’s book “Let Your Life Speak” - http://www.amazon.com/Let-Your-Life-Speak-Listening/dp/0787947350

"Never let the odds keep you from doing what you know in your heart you were meant to do.” - H. Jackson Brown, Jr. Have you ever asked yourself the question: I wonder if we'd be better off with someone else in my role? In this podcast, a listener, Kent Cavender-Bares from Rowbots, comes to Jerry with a similar question: "What if my deep integrity, my commitment to simply telling how it is, is the reason we’re unable to fundraise? Do I even have a Superpower? Wouldn’t Rowbots be further along if someone else was leading?" Jerry and Kent explore the double edge of a superpower, and how the path through Kent's challenges may lie in a new set of questions: How can I be even more like Kent? How can I embrace my superpower? How can I believe in myself? And why is that so damned important? Links Rowbot - http://rowbot.com/ Rowbot on Twitter - https://twitter.com/rowbotsystems Kent Cavender-Bares on Twitter - https://twitter.com/kbares Parker Palmer - https://en.wikipedia.org/wiki/Parker_Palmer Jerry’s post, “The Crucible of Leadership,” on Fred Wilson’s blog - http://avc.com/2012/02/the-management-team-guest-post-by-jerry-colonna/ David Whyte’s brilliant book, “Crossing the Unknown Sea” - http://www.amazon.com/Crossing-Unknown-Sea-Pilgrimage-Identity/dp/1573229148

“Be yourself; everyone else is already taken.” - Oscar Wilde 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 with entrepreneurs through those challenges. This conversation may leave you asking yourself: In my own work, what are my values? What are my priorities? What am I wearing today? Links Bryce Roberts on Twitter - https://twitter.com/bryce Chris Marks on Twitter - https://twitter.com/bluenotevc Indie.vc - http://indie.vc Blue Note Ventures - http://bluenotevc.com O’Reilly Alphatech Ventures - http://oatv.com Bryce’s blog post - The Peace Dividend of the Seed Surge - http://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/ Aileen Lee’s article on on Unicorn startups - http://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/http://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/

“Authenticity is the alignment of head, mouth, heart, and feet - thinking, saying, feeling, and doing the same thing - consistently. This builds trust, and followers love leaders they can trust.” - Lance Secretan So many entrepreneurs seek to model their leadership after the high-profile, successful giants. Should I be a leader more like Steve Jobs? How can I be more like Jeff Bezos? How can I be more like Travis from Uber? These are not only questions without answers, they are the wrong questions. The real question is, “Who the fuck are you?” You’re not Steve Jobs. You’re not Jeff Bezos. You’re you. What does the leader within you look like? In today’s conversation, Jerry is joined by Evgeny Shadchnev, Co-founder and CEO of Makers Academy. Ev wrestles with the question of whether it’s possible to scale an organization built around trust, or does success require a leader who governs by fear. Together they discover a more beautiful, more fundamental question --“Who is Evgeny?” In that answer they may find a path to personal alignment and more effective leadership. Links Makers Academy - http://www.makersacademy.com Makers Academy Twitter - https://twitter.com/makersacademy Evgeny Shadchnev Twitter - https://twitter.com/shadchnev

“Watch carefully the magic that occurs when you give a person just enough comfort to be themselves.” – Atticus Finch There’s a saying: Behind every great man is a great woman. I would add: behind every great entrepreneur is a great friend. The entrepreneurial path simply can’t be traveled alone. So when Jerry asked Kickstarter’s CEO and Co-founder, Yancey Strickler: Who do you turn to? He response was immediate: Ian Hogarth, Co-founder and Chairman of Songkick. We’re grateful to have Yancey and Ian join Jerry in today’s podcast to talk about their friendship, the importance of peer relationships in entrepreneurship, the relief of being heard by those who can empathize with your experience, as well as those who can challenge you from a place of love and deep understanding. Enjoy this discussion with Jerry, Ian Hogarth, and Yancey Strickler. This conversation was recorded in early December, and since then Ian has announced his intention to give up the Co-CEO role at Soundkick and focus on his role at Chairman. I’d encourage to read his very well written blog post on this transition here ( http://soundboy.tumblr.com/post/136337729790/new-year-new-roles ). Links Yancey’s blog - http://yancey.tumblr.com/about Ian’s blog - http://soundboy.tumblr.com/about Yancy Strickler on Twitter - https://twitter.com/ystrickler Ian Hogarth on Twitter - https://twitter.com/soundboy Kickstarter - https://www.kickstarter.com Songkick - https://twitter.com/songkick

“Life doesn't run away from nobody. Life runs at people.” - Joe Frazier Carrie Barry has had great challenges to overcome, including real struggles at home that forced her to leave at the age of 12 and strike out on her own. She’s proven resilient, stitching the struggles of her past into the fabric of her being and choosing to appreciate and utilize that pain into the work she does today. Carrie Barry is a former Olympic Boxer and entrepreneur who owns and runs a boxing gym in Boulder where people come to break a sweat, get a hug, and learn some valuable life lessons. She also happens to be, in a twist, a boxing coach for 2 of Reboot’s finest: Jerry and Ali. Join Jerry in getting a little coaching, and a lot of inspiration in this conversation with Carrie Barry. Links The Corner Boxing Club - http://www.thecornerboxing.com The Corner Boxing Club on Twitter - https://twitter.com/thecornerboxing

The shadow is everything about ourselves that we do not know or refuse to know, both dark and light. It is the sum total of the positive and negative traits, feelings, beliefs, and potentials we refuse to identify as our own. The shadow is that part of us that is incompatible with who we think we are or are supposed to be. - David Richo Tracy Lawrence, Co-founder and CEO of Chewse, and Jerry talk about authenticity, leading from the heart, and the power of embracing the lost and disowned parts of ourselves. 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 her approach to the latest company experiment, but it also might affect her own leadership and bring her and her company deeper into alignment. links Chewse - https://www.chewse.com Tracy Lawrence on Twitter https://twitter.com/chewishgirl "Shadow Dance" by David Richo http://www.amazon.com/Shadow-Dance-Liberating-Power-Creativity/dp/1570624445 Buffer open salaries blog post https://open.buffer.com/introducing-open-salaries-at-buffer-including-our-transparent-formula-and-all-individual-salaries/

Full notes at Reboot.io/podcast "From caring comes courage." -Lao Tzu It’s wonderful to have the support of so many, to have so many who believe in you. But there is another side to it: the weight and fear of disappointing them. Zoe Weintraub is founder of Opus for Work and is our guest on this episode of the podcast. Zoe and Jerry discuss both the beauty and burden of external expectations, and ultimately find that when you follow the emotion and vulnerability associated with them, they expose your superpower hiding in plain sight. Links Opus for Work - https://www.opusforwork.com Zoe Weintraub on Twitter - https://twitter.com/ZoeWeintraub Opus for Work on Twitter - https://twitter.com/OpusForWork

Full notes at Reboot.io/podcast “...the greatest gift of relationship proves to be that as the result of encountering each other, we are obliged to grow larger than we had planned.” - James Hollis Two co-founders, who refer to each other as business soulmates, have found themselves in that special place of alignment. A place in partnership where they align not just intellectually, not just energetically, not even just at a values level, but at a human level. Jules Pieri (her second time on the show) and her partner Joanne Domeniconi are the co-founders of The Grommet. They join Jerry to talk about the beginning of their partnership, where and how they found alignment at the human level, how it has evolved over time, and the challenges it represents as they scale the business. Links The Grommet - thegrommet.com The Grommet on Twitter - https://twitter.com/TheGrommet Jules Pieri - https://twitter.com/julespieri Joanne Domenic - https://twitter.com/jdomeniconi Fred Wilson - https://en.wikipedia.org/wiki/Fred_Wilson_(financier) Mark Pincus - https://en.wikipedia.org/wiki/Mark_Pincus Sunil Paul - https://en.wikipedia.org/wiki/Sunil_Paul David Whyte - http://www.davidwhyte.com How to Be an Adult in Relationships by David Richo - http://www.amazon.com/How-Be-Adult-Relationships-Mindful/dp/1570628122 The Center for Collaborative Awareness - http://www.blueprintofwe.com/cfca.html Parker Palmer - http://www.couragerenewal.org/parker/

Full notes at Reboot.io/podcast "Can we live beyond compare?" -David Richo Brad Feld is an investor, entrepreneur, and blogger who has been supporting entrepreneurs all over the world since 1987. Brad has also been a great Reboot supporter and teacher. In this conversation, Brad joins Jerry Colonna to talk about VC’s as Dungeons and Dragons characters, Brad’s evolved investment criteria, and the single best piece of advice Brad offered to Jerry that changed his career. Links Feld Thoughts Blog - http://www.feld.com Something New is Fucked Up In My World Every Day by Brad Feld - http://www.feld.com/archives/2015/04/something-new-fucked-world-every-day.html Foundry Group - http://www.foundrygroup.com Anchor Point Fellows Program at Wellesley College - http://anchorpoint.blogs.com/amythoughts/2013/08/albania-to-zimbabwe-anchor-point-internships-in-global-leadership-conference.html

Full notes at Reboot.io/podcast See Hugh's special Reboot inspired cartoons on the show notes linked above. Hugh MacLeod has tapped into his own heart and his own woundedness so that he can speak to the hearts of people and organizations to inspire, to question, to laugh and to grow. Hugh joins Jerry in this episode of The Reboot Podcast to discuss how how he got his start, what motivates leaders, and how to work (and lead) from the heart. (Hint: often the "how" lies in identifying our own wounds). Hugh’s Cartoon - “I am not delusional. I am an entrepreneur.” - http://gapingvoid.com/blog/2009/10/18/im-not-delusional/

Full notes at Reboot.io/podcast "With a little more care, a little more courage, and, above all, a little more soul, our lives can be so easily discovered and celebrated in work, and not, as now, squandered and lost in its shadow.” - David Whyte Sometimes we spend so much time looking at where we aren’t or where others have gone that we don’t fully appreciate where we are and how much we’ve grown on the journey. A year ago today, Reboot didn’t have a podcast. A year ago today, Sherman Lee was staring down a draining bank account, a shaky business model, and a crippling fear: if I fail, I won’t be able to provide. A year later we sit with our 23rd podcast episode, a return visit from one of our first guests, Sherman Lee, and an opportunity to appreciate Sherman’s journey and growth since we last spoke. Links Episode notes -https://www.reboot.io/episode/23-with-a-little-more-care-with-sherman-lee-and-jerry-colonna/ Good Audience - http://www.goodaudience.com Good Audience on Twitter - https://twitter.com/GoodAudience Sherman Lee on Twitter - https://twitter.com/SHERM8N

We’re often in (or feel we’re in) uncharted waters - a place where making things up as we go is a necessity. Feeling lost in those places can be anxiety-inducing. We feel incompetent. We feel shameful. We can end up feeling that everyone has figured it out but me. But how true is that, really? And perhaps the better question--how can owning my own anxiety in these areas help me step more fully into my authentic self and even increase my capacity for happiness? We are honored to welcome one of our key teachers at Reboot, Sharon Salzberg, to the podcast. In this conversation Sharon and Jerry discuss Sharon’s entrepreneurial path, a new definition of success (and failure), authenticity, loving kindness, and the question: Does anyone really know what they are doing? Sharon Salzberg on Twitter - https://twitter.com/SharonSalzberg Insight Meditation Society - https://en.wikipedia.org/wiki/Insight_Meditation_Society Lovingkindness - http://www.amazon.com/Lovingkindness-Revolutionary-Happiness-Shambhala-Classics/dp/157062903X Real Happiness - http://www.amazon.com/Real-Happiness-Meditation-28-Day-Program/dp/0761159258 Real Happiness at Work - http://www.amazon.com/Real-Happiness-Work-Meditations-Accomplishment/dp/0761168990

"I would love to live like a river flows, carried by the surprise of its own unfolding." John O'Donohue The ups and downs, the hills and valleys, the ebb and flow, the rollercoaster - there are many ways to describe the emotional journey of being an entrepreneur. There are also many, many ways we try to straighten out and control the journey. We look to “optimize” for the peaks and minimize the valleys. But what if we’re looking at it all wrong? In this episode of the Reboot podcast, Jerry is joined by Bill Morrision, founder of Constellation Behavioral Health, which offers specialized treatment programs for alcohol and drug addiction. With Jerry, Bill explores the deep and complicated connections between his purpose, his mission, the peaks, the valleys, and the fear of going off plan. Constellation Behavioral Health - http://www.constellationbehavioralhealth.com Alta Mira Recovery Programs - http://www.constellationbehavioralhealth.com/alta-mira/ Jerry’s blog post “Up and to the Right” - http://www.themonsterinyourhead.com/2014/05/18/up-and-to-the-right/ Pema Chodron’s “Comfortable with Uncertainty” - http://www.amazon.com/Comfortable-Uncertainty-Cultivating-Fearlessness-Compassion/dp/1590300785

full show notes: reboot.io/podcast "Everyone thinks of changing the world, but no one thinks of changing himself." - Leo Tolstoy It sounds so obvious, perhaps even tongue in cheek, but it also seems to be forgotten enough that it needs to be said aloud again: Investors are human too. They, like the entrepreneurs they back, can ride the rollercoaster of emotions that often come with starting a company. In this episode Jerry Colonna is joined by Bijan Sabet of Spark Capital to explore some of the tensions that often arise between investors and entrepreneurs, the emotional perspective of the investor, and the importance of purpose and artistry. As a bonus, it includes Jerry reading a blessing at the end. ©2015 Reboot.io Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported http://creativecommons.org/licenses/by-nc-sa/3.0/

For more go to reboot.io/podcast What’s it like to find your path of authentic service in the world? What if you could use the pain of the past, a pain of not knowing where you fit in, of not knowing where you belong to propel you toward work that makes a difference? What if you could create a place of belonging? Well, it might look a lot like what Tanisha Robinson is building with Print Syndicate. Started just 2.5 years ago with 8 people, Print Syndicate now has over 140 employees and will generate more than $20M in revenue this year. But the company isn’t just about shirts and home goods, it’s a place where people (including a black, gay, woman from a Mormon family of 7 in a small town in Missouri) have a place to self-identify and a place to belong. As Tanisha shares, running a company fueled by your passion to make the world better is both exhilarating and heart wrenching. ©2015 Reboot.io Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported http://creativecommons.org/licenses/by-nc-sa/3.0/

see more at: http://reboot.io/podcast Fear is a familiar and powerful co-founder in startups. We do our best to quiet it, shut it down, deny it. Perhaps our biggest struggle is simply acknowledging it. But what if you not only acknowledged your fear, but leaned into it? What if you let go of your own hope to control things, and go back to building and leading from a place of love? Jules Pierri, cofounder and ceo of the product launch platform the Grommet, has done just that for her growing team of 55 employees. In this conversation, Jules and Jerry discuss what it was like to embrace the grit of her Detroit working class upbringing, face head on the fears of being a non-prototypical entrepreneur building a new kind of company in one of the scariest economic times in recent memory. Through it all, Jules has been able to move forward with courage to build an organization where people can feel loved and do great work in the process.

see more at: http://reboot.io/podcast “A good half of the art of living is resilience.” ― Alain de Botton Nigel Sharp, our first returning podcast guest, is wrestling with one of the hardest any entrepreneur can ask themselves: Am I being stubborn or resilient? Shouldering the hope and opportunity of improving a country through his organization and carrying a real concern for his own team, he stares down an empty company bank account, wrestling with a deep confusion whether he should push on or move on. Jerry and Nigel explore the questions he’s holding, what moves him personally about his business, and where to possibly go next.

see more at: http://reboot.io/podcast What if your agreements with partners and co-workers were more focused on the characteristics of how you come together, related to one another, and work together, instead of what happens when sh*t hits the fan? What if your co-founder agreement came from a place of hope instead of fear? Zelle Nelson and Maureen McCarthy are co-founders of The Center For Collaborative Awareness and our guests for today’s conversation. They’ve created a collaborative process called “The Blueprint of We,” used to build and sustain healthier, more resilient business and personal relationships - those that start from a place of hope and openness. They join Jerry to share how they came together, how the process works, and how this work can impact your relationships and your organization.

For full video visit: https://www.reboot.io/podcast JW Player has come a long way. The JW player and platform is now used by over 2.5 million publishers and 20% of the fortune 1,000 companies. Each month about 1 billion people watch video on their platform. Behind those numbers are real people--including three co-founders who, over the last eight years, have experienced their own profound personal growth and leadership transformations. In a special first video episode, only fitting for the co-founders of one of the world’s largest video platforms, we have the 3 co-founders of JW Player (Dave Otten, Jeroen "JW" Wijering, and Brian Rifkin) joining Jerry in person. In a very open conversation, they explore key challenging moments in their company and partnership history -and how they emerged from those moments stronger and more committed than ever. It's an inspiring story of leaders born through adversity

Full notes and more: reboot.io/podcast Who are you? What do you believe to be true? What do you bring consciously to the world? And, even more interesting, what do you bring unconsciously to your work, your organization, your relationships? How does that which you have either denied about yourself, or feel uncomfortable about, shape your life, either positively or negatively? What lies in this unseen shadow? And why is it important for you to explore? The work of today’s guest shows up in just about everything we do here at Reboot so we are thrilled to have one of our key teachers, Parker Palmer, join Jerry for a discussion on a very important and powerful topic: Shadow and Leadership.

To have a firm persuasion, to set out boldly in our work, is to make a pilgrimage of our labors, to understand that the consummation of work lies not only in what we have done but who we become while accomplishing the task. -David Whyte - Crossing the Unknown Sea: Work as a Pilgrimage of Identity Show notes (and more): reboot.io/podcast In today’s conversation Jerry is joined by Ben Rubin - Cofounder and CEO of Change Collective - an organization itself that is set on helping people make positive change in their lives. Ben comes to Jerry wondering how he can better deal with the negative inner dialogue. They quickly discover that inner voice, and more specifically the feelings that precede it, are a powerful indicator of an underlying fear. What opportunities exist in exploring that fear?

Difficulties are just things to overcome, after all. -- Sir. Ernest Shackleton Ben Saunders knows very well the ups and downs that come with attempting to do something groundbreaking. Like so many entrepreneurs, he struggled with the challenges of being an effective leader, and faced the pain of fundraising or not meeting payroll. But Ben’s end goal was a bit different. He’ a polar explorer. Between October 2013 and February 2014, he and his companion Tarka broke the record for the longest ever polar journey on foot. On their path to the South Pole, they faced temps of -50F and windchills near seventy below all while they covered nearly seventy marathons back-to-back on less than four hours of sleep a night. This record breaking journey was nearly ten years in the making for Ben, and truly was an amazing accomplishment, but despite all that he found the inner journey that followed even more challenging. In this conversation, Ben and Jerry discuss Ben's journey on and off the ice.

“Consciousness is so turbulent” - Emily Horn Vincent Horn is a mind hacker & Buddhist geek. He has been practicing meditation intensively since his freshman year in college. In 2006, Vincent co-founded Buddhist Geeks, which has gone on to become one of today's most important venues for exploring Buddhist thought & practice in the 21st century. Buddhist Geeks has been featured on the pages of the Los Angeles Times, The Guardian, Tricycle, and The Atlantic. Vincent was also honored to be part of Wired’s "Smart List 2012: 50 people who will change the world." In this episode, Vincent and Jerry talk about their mindfulness practices, how Vincent navigated his own ups and downs as an entrepreneur, and how meditation and mindfulness can create better leaders, and better organizations. And be sure to listen all the way through the end, as Vincent has included a 10 minute guided meditation for you to kickstart your own mindfulness practice.

“I have not failed. I've just found 10,000 ways that won't work.” ― Thomas A. Edison Most startups fail. We all know this as much as we try to forget it. The absolute hardest, hardest question an entrepreneur can ask themselves is: When do you know it’s over? In the first of two conversations in this episode, we are joined by Derek Bereit, CEO and Co-Founder of Symptomly, who is staring down the end of his runway and wrestling with this very question. In a second conversation we hear from Beth McKeon, Founder and CEO of Kids Calendar, who is dealing with another common challenge: How do you find, recruit and hire the right person for your startup at the stage that it’s in? As always we’d love to hear feedback from you either on our website or on twitter @reboothq. Now on with to the conversations.

Be Without Deception Being without deception is an extension of telling the truth: it is based on being truthful with yourself. When you have a sense of trusting your own existence, then what you communicate to other people is genuine and trustworthy. -Chogyam Trungpa Rinpoche In 19 years of friendship and partnership in the startup world, these two 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. In what we hope will be a series of several, enjoy this first Reboot conversation with Fred Wilson and Jerry Colonna.

“Knowing yourself is the beginning of all wisdom.” ― Aristotle For notes and more: http://www.reboot.io Entrepreneur and CEO Blaine Vess has an impressive story. Studymode, the company he helped start and bootstrap from his dorm room almost 16 years ago, now has 30 employees and sees between 60-90M visitors a month. It’s rare to find 15 year old bootstrapped companies. It’s rare to have the same CEO for 15 years as Blaine has been. But last year, Blaine wanted more for his company and himself. He wanted to know how to help push his company to the next level. To achieve that, he didn’t look elsewhere, he looked within. In this conversation, Jerry and Blaine talk about Blaine’s “year of introspection”. It included a stop at one of our bootcamps, working with a coach and a therapist, and that year ultimately helped him understand how and why he was holding himself back. Perhaps Blaine and Jerry’s conversation, our first of 2015, may spark your own year of introspection.

After years of rapid growth and expansion, followed by a serious year of depression, Rand Fishkin, founder and former CEO of Moz, found himself in a room surrounded by VC backed CEO’s and entrepreneurs where the question was posed: “How many of you struggle seriously with depression or severe anxiety or emotional issues?” He watched almost every person raise their hand. It’s shocking how universal depression is in startups. For anyone struggling with depression, it’s helpful to know you’re not alone. In this podcast, which is slightly different than past episodes, Jerry converses with Rand about his experience - his “loop,” how shame and guilt are at times his driver, the importance of understanding one’s emotional state, and how he’s made progress in coming out of his own depression, including his one piece of advice for entrepreneurs or anyone dealing with their own depression.

Do you have an innate desire to make people happy? And does that desire at times cause you to at hold back the truth, out of fear of perhaps hurting others and yourself? Carm Huntress is the CEO of RxReview, a company solving a big problem with big data - overspending on prescription drugs. The company started in January 2012 and is growing beyond it’s 11 employees. Carm realizes his nature as a people pleaser affects his leadership in detrimental ways. In this episode, Jerry and Carm unpack what it means to be fierce, and what’s behind the desire to make people happy. It’s a conversation that will leave you asking: “What if I led from a place where I knew I was good and also know there are things I want to do better?”

Joseph Chura is the founder and CEO of 2 startups that employ nearly a combined 100 people, yet he feels a constant drive for more. In this conversation with Jerry, Joseph shares his struggles to be present, especially at home with his wife and kids and they explore the question: Why is the drive to succeed, the itch to not sit still, so strong?

How can you save a business from the brink of bankruptcy and grow it 2,000% in 10 years, and yet feel like it could all go away in any given moment? Or face the fear, the weight, that you must be chief breadwinner...for you, your family, your co-founder and team’s family as well? Fear is pervasive in our lives, and in the crazy world of startups and entrepreneurship it is an always present participant. In this episode, we have two entrepreneurs dealing with two different and yet similar fears, fears that entrepreneurs will know all too well.

As CEO of a young startup, you can often feel what you are facing right now can make or break your company, can make or break you. And you will likely find yourself in this place more than once. Nigel Sharp, CEO of Armenian based Lion Sharp, finds himself in one of these very moments. He feels the energy of a promising product, and the reality of 6 months of runway. How do you balance the excitement and challenges? How do discuss the reality of your finances with your team? How do you discuss your fears, not only of failure but of success?

Duncan Morris, by any measure, had achieved a great deal success as co-founder and CEO of the international, 60 employee, online marketing agency - Distilled.net. And yet, something felt off for him. At our bootcamp in June he was touched and challenged by a question from Jerry: “What if you could truly understand who you are, and lead from that place?” In evaluating this question, a new question emerged for Duncan: “What if I don’t want to be a leader of a company with 60+ people?” In this conversation with Jerry, hear how exploring these questions has ultimately changed his work, his company, and his life.

Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joins Jerry for this episode to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended a CEO bootcamp last October and begin to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge that could have destroyed his business. Derek’s openness and introspection is inspiring, and will inspire you to re-examine how your own stories impact your business and your life.