The Reboot Podcast

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 R

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 revi

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: L

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 fo

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 a

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 ack

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: - 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 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 sea

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 ta

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: - How To: Leave a Review on Your iPhone: Never miss an episode! Sig

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: - 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 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 e

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." ( ). 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: - 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.

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 Jef

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 rel

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