
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

May 10, 2022 • 52min
#157 - When Are You Done? - with Chris Remus & Jerry Colonna
In this podcast, Jerry sits down with Chris Remus, Founder of Chainflow, to explore an enormously complex and personal question, “What does it mean to be done?” What unfolds is a thought-provoking conversation around our relationship to work, and why we so often sacrifice our personal happiness in the pursuit of ‘doneness.’ Chris reflects on the ways in which the misalignment between his inner and outer self left him feeling unsafe and sapped his ability to fully tap into his potential. Jerry supports Chris in understanding that the real work of our lives is never truly ‘done,’ especially when we allow the junctures we arrive at and pass through to be greater tools for connecting to purpose and our heart’s greatest desires. 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.

Apr 26, 2022 • 48min
Reboot Extra #13 - Navigating High Conflict Personalities - with Megan Hunter & Ali Schultz
Have you ever encountered a person in your life who you couldn’t reason with the same way you could with so many others in your life? Are there some folks that make you act differently, or feel like you walk on eggshells around them? In this podcast, Ali sits down with Megan Hunter, a co-founder of The High Conflict Institute and expert on High Conflict Personalities (also known as HCPs). The pair discuss the five types of HCPs and explore how the HCP brain works differently (and what that means for interactions with them). Megan describes what to do if you find yourself as a Target of Blame and shares tools and approaches for navigating these personalities, as well as what not to do. 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.

Apr 12, 2022 • 52min
#156 - Safety and Trust: The Crux of Adult Relationships - with Brad Feld & David Jilk
At Reboot, we firmly believe that the act of leadership affords everyone the opportunity to grow into their most adult selves. Inquiring radically into our own psychologies and facing up to the truths behind our behavior allows us to lead and relate to others from a more informed place. In this podcast, Jerry sits down with Brad Feld and David Jilk, co-authors of "Entrepreneur's Weekly Nietzsche: A Book for Disruptors". The duo, who’ve shared a personal and professional relationship for nearly forty years, share why collaborating effectively requires honesty, respect, and the ability to lean into healthy conflict when it arises. Jerry, Dave, and Brad emphasize the importance of setting, communicating, and honoring boundaries, and highlight why safety and trust are at the crux of all healthy, adult relationships. 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.

Mar 29, 2022 • 8min
Reboot Extra #12: Compassionate Abiding: A Guided Meditation for Anxious Times with Marty Janowitz
What does it feel like to connect deeply with the groundlessness that arises during times of anxiety? In this short clip, Reboot Coach and Facilitator Marty Janowitz leads a short meditation practice in compassionate abiding. In this introductory practice, you’ll focus on breathwork, sitting with uncertainty, and discovering what it means to reconnect with the cradle of our lovingkindness. 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.

Mar 17, 2022 • 49min
Reboot Extra #11: Women's Conversations - Finding Joy & Creative Habits - with Rachel Ryle & Ali Schultz
In this Podcast Extra, Reboot Co-founder Ali Schultz sits down with Rachel Ryle, an award-winning animator, illustrator, and storyteller. Rachel describes how tending to her energy and taking ownership of her mental health has brought more purpose and fulfillment to her everyday life. She describes her daily gratitude practice and details how leaning into joyful pursuits has reinvigorated her creativity and boosted productivity. 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.

Mar 6, 2022 • 49min
#155 - The Heart of the Matter - with Simon Maltais & Jerry Colonna
As the Coronavirus pandemic continues to shape our lives, many of us are flat-out exhausted. While this enduring moment in time has impacted us all, the prolonged nature of this global public health crisis has left healthcare workers feeling physically and mentally exhausted. Burnout, it’s a topic that we often address on the Reboot Podcast, and a term we’ve all been hearing more and more over the course of the past few years. For cardiac surgeon Dr. Simon Maltais, long hours in a demanding work environment were to be expected, but slowly, over time, when he looked in the mirror, the outer Simon was becoming unrecognizable to the inner Simon. In this conversation, he shares how his quest for perfection, and his desire to “sparkle and be loved” led him down a destructive path fueled by alcohol, anger, and self-criticism. Jerry and Simon discuss the high rates of depression and burnout among healthcare professionals and the resilience they need to deal with the suffering that surrounds them. In sharing honestly about his experience, Simon hopes that his fellow colleagues in healthcare and others in high intensity environments will feel less alone. 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.

Feb 15, 2022 • 54min
#154 - Untying the Knot of the Heart - with Duff McDonald & Jerry Colonna
When we’re so committed to being right about our own reality, we miss things happening right under our nose. Egos are handy, but they can be limiting to the amount of joy we experience in life if we let them lead the way. In this episode Duff McDonald, journalist and author of "Tickled: A Commonsense Guide to the Present Moment", recounts how the quiet of quarantine shocked him out of his narrow perspective of living, and turned his way of being on its head. Duff describes how the gift of fallow time forced him to thinking radically about how he’d been operating in the world up until that point, and shares how untying the knot of his heart produced a fire hydrant of love, opening him up to the magic of life itself. 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.

Feb 8, 2022 • 6min
Reboot Extra #10: Drawing From the Power of Our Ancestors: A Guided Visualization with Jamie Kim
How often do you connect with those who came before you? What do you know about them? What was life like for them? What did they live through? What were their unfulfilled dreams? What stories are still alive in your family to this day? When doing the work of learning about our past, we can forget that we are here because of many generations of love expressing itself. In this podcast Extra, Jamie Kim offers a visualization to connect with those who came before you and to feel the magnitude of that love and support. 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.

Jan 25, 2022 • 13min
Operator's Manual #4: On Modeling Self-care and Building the Machine - with Ali Schultz & Jerry Colonna
In this episode of our Operator's Manual series, Ali and Jerry consider how the health and resilience of an organization can be directly tied to the CEO’s own modeled behavior around self-care. Jerry reminds us that the CEO’s job is to build the machine that builds the products and services, not to build the products and services. 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.

Jan 11, 2022 • 42min
#153 - Everyone Is Scalable - with Matt Blumberg & Jerry Colonna
Matt Blumberg, founder and CEO of Bolster, shares his insights on entrepreneurship after years of leading Return Path. He discusses the transition to launching Bolster in his 50s, emphasizing the need for a seasoned team. The conversation touches on his book, Startup CXO, which outlines essential skills for functional roles. They also explore the advantages of using fractional executives to scale efficiently and highlight the importance of empathy and proactive planning in leadership, especially for founders navigating diverse roles.