
The Reboot Podcast
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.
Latest episodes

Aug 16, 2019 • 40min
#110 - The Mother of Invention - with Jules Pieri & Jerry Colonna
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! Sign up for our newsletter to stay up to date on all our episode releases.

Jul 25, 2019 • 1h 18min
#109 - With Great Power Comes Great Responsibility - with Dan Harris & Jerry Colonna
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.

Jul 12, 2019 • 59min
#108 - Leading Shoulder to Shoulder - with Sara Hicks & Mathias Meyer
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: - 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.

4 snips
Jun 18, 2019 • 30min
#107 - Reboot: Leadership & the Art of Growing Up - with Jerry Colonna
Author Jerry Colonna discusses his new book 'Reboot: Leadership and the Art of Growing Up' and shares insights on radical self-inquiry, leading authentically, and aligning inner and outer selves. He emphasizes the value of journaling for personal growth and explores the dynamic nature of work and leadership practice.

Jun 6, 2019 • 1h 3min
#106 - Chasing Purpose - with Jeff Orlowski & Jerry Colonna
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

May 23, 2019 • 49min
#105 - Reboot Your Definition of Success - with Alex Rethore & Jerry Colonna
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: - 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.

May 10, 2019 • 56min
#104 - The Next Chapter - with David Ryan & Jerry Colonna
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

Apr 27, 2019 • 56min
#103 - What Kind of Company Do You Want to Work For? - with Chris Savage & Brendan Schwartz
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: - 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.

Apr 4, 2019 • 60min
#102 – To Actually Live Your Life – with Khe Hy & Jerry Colonna
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: - 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.

Mar 21, 2019 • 50min
#101 – A More Powerful Way of Working – with Patty McCord & Jerry Colonna
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: - 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.