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The Reboot Podcast

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The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.
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The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.






#81 The Identities That Rule Us - with Semil Shah & Jerry Colonna

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...


#79 The Space Between Stimulus and Response - with Nicole Glaros & Jerry Colonna

“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...


#77 Knowing You’re Not Alone: The Magic of Peer Groups - with Jerry Colonna

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...


#75 A Pattern of Habits - with Judson Brewer & Jerry Colonna

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 -...


#74 How Human Can We Be as Leaders? - with Tarikh Korula & Jerry Colonna

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...


#72 Heeding Life’s Speed Bumps - with Matt Tara & Jerry Colonna

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...


#71 Patience and Persistence - with Bobby Brannigan & Jerry Colonna

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...


#69 Effective Communication for a Growing Team - with Erin Frey & Ti Zhao

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...


#68 Your Second Act - with Jason Jacobs & Jerry Colonna

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...


#67 The Energy of Our Emotions - with Dan Harris & Ben Rubin

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...


#65 What You Choose to Become - with Jerry Colonna and Derek Flanzraich

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...


#64 Whole Humans Make Better Leaders - with Nancy Lublin & Jerry Colonna

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...


#63 Remember Who You Are - with Adi Mashiach & Jerry Colonna

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...


#62 Letting Go of Perfection - with Sharon Salzberg & Jerry Colonna

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...


#61 The Seasons of Our Lives - with Sally Spencer & Jerry Colonna

Sally Spencer-Thomas is a psychotherapist who found herself in a moment in which she was not prepared when her brother committed suicide. After that significant event in her life, Sally poured much of her life into building awareness and leading innovation in suicide prevention through the Carson J. Spencer Foundation. 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...


#60 The Work of Your Life - with Khe Hy & Jerry Colonna

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...


#59 Everything is Waiting for You - with Al Doan and Jerry Colonna

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...


#58 The Joy of Surrender - with Simon Cant and Jerry Colonna

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...


#56 Participate in Your Own Rescue - with John Guydon & Jerry Colonna

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...


#55 Fierce Compassion - with Roshi Joan Halifax & Jerry Colonna

"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...