The Reboot Podcast

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 pre

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

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 com

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 with

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

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

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 cap

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 drivi

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 - Konda Mason on Twitter - Impact Hub Oakland - Spirit Rock Meditation Center - 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: L

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, inh

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 difficul

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 ta

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/

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 - Kent Cavender-Bares on Twitter - 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! 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 no

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 - Al Doan on Twitter - Signs you need to leave your startup - CEO bootcamp - Reboot Circles - Episode #29 Who’s in your corner? With Carrie Barry - Episode #77: Knowing You’re Not Alone, The Magic of Peer Groups -   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! 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. Perha

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

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 -

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 - The Center for Courage and Renewal - The Courage Way: Leading and Living with Integrity - The Möbius Strip - Leave us