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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.






#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...

Duration: 00:53:33

#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...

Duration: 00:49:06

#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...

Duration: 01:06:20

#66 What Are You Made Of? - with Jerry Colonna & Adeesh Agarwal

Adeesh Agarwal is an architect who has worked in real estate, med-tech, and had started and managed his own design firm, which recently closed it’s doors. He finds himself soul searching at 40 years old looking back at the choices he’s made to have a job and be a responsible caretaker for his family. He struggles with finding work that isn’t soul-sucking, that creates safety and opportunity for his family, and wanting to have a sense of stability and sense of progress in his life. As he...

Duration: 01:02:26

#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...

Duration: 00:53:08

#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...

Duration: 00:49:35

#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...

Duration: 00:44:45

#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...

Duration: 00:44:38

#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...

Duration: 01:02:24

#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...

Duration: 00:55:22

#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...

Duration: 00:39:31

#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...

Duration: 00:42:18

#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...

Duration: 00:46:22

#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...

Duration: 00:46:49

#54 Hearts Broken Open - with Matt Munson & Jerry Colonna

A disciple asks the rebbe: “Why does Torah tell us to ‘place these words upon your hearts’? Why does it not tell us to place these holy words in our hearts?” The rebbe answers: “It is because as we are, our hearts are closed, and we cannot place the holy words in our hearts. So we place them on top of our hearts. And there they stay until, one day, the heart breaks and the words fall in.” - Hasidic Tale, as told by Parker Palmer Every entrepreneur hears the call of an inner voice. We may...

Duration: 00:50:18

#53 Transform Your Hustle - with Catherine Hoke & Brad Feld

Almost all successful entrepreneurs will fail - if not fail, fail, fail, and fail again - on their path to success. Every human being made choices in their lives which they regret, are embarrassed of and have caused them deep shame. What would your life be like if you were known only by the worst thing you had ever done? Catherine Hoke is the founder of Defy Ventures, a program that helps incarcerated individuals transform their hustle to entrepreneurial ventures. Following a chance visit...

Duration: 01:04:32

#52 Feast on Your Life - with Rob Symington & Jerry Colonna

“If we hope to go anywhere or develop ourselves in any way, we can only step from where we are standing. If we don't really know where we are standing... We may only go in circles...” ― John Kabat-Zinn The Reboot podcast was started because we believed that there needed to be an authentic, real conversation about the emotional journey of entrepreneurship. One that included its valleys and not just its peaks. One in three entrepreneurs will struggle with depression or burnout in their...

Duration: 00:52:38

#51 The Love that Heals: Welcoming in Our Shadow - with Jerry Colonna & James Hollis

“One does not become enlightened by imagining figures of light, but by making the darkness conscious. The latter procedure, however, is disagreeable and therefore not popular.” - C.G. Jung 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...

Duration: 00:44:30

#47 Embracing Both Sides of Yourself - with Amir Salihefendic & Jerry Colonna

“I am not what has happened to me, I am what I choose to become.” - Carl Jung Amir Salihefendic, the founder and CEO of Doist, is the creator of the powerful and popular productivity tool, Todoist (which is awesome). He comes to Jerry feeling torn between two seemingly different directions for his business. On one side, he feels the ambition to do big, world changing things and to be on every smartphone and desktop. But on the other side, as the son of entrepreneurial parents who owned a...

Duration: 00:42:00

#46 Hitting a Wall - with Semil Shah & Jerry Colonna

“Most of us have two lives. The life we live, and the unlived life within us. Between the two stands Resistance.” ― Steven Pressfield "The War of Art" Semil Shah has done remarkably well as a one-man shop, but he is wrestling with the challenges of growing his business and being with his growing family of 5, while continuing to grow himself. Adding to those challenges, there’s also a sneaky voice for him, one that can drive him and also hold him back, one that is saying to him: “You don’t...

Duration: 00:34:34

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