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 surrende...
Apr 06, 2017•41 min
“If we have no peace, it is because we have forgotten that we belong to each other.” - Mother Teresa For Bijan Sabet- an investor, US citizen by birth and descendant of Korean and Iranian immigrants- the January 27th Trump administration issue of an executive order banning the entry of residents and refugees from a number of Muslim countries deeply disturbed him for a number of reasons. Recalling his own early experience of being othered as the child of an Iranian immigrant during the Iran Hosta...
Mar 23, 2017•38 min
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 since tha...
Mar 09, 2017•45 min
"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 allocate...
Feb 16, 2017•45 min
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 call it...
Jan 26, 2017•49 min
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 (as a ...
Jan 19, 2017•1 hr 3 min
“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 career, yet...
Dec 15, 2016•51 min
“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 to mak...
Nov 23, 2016•43 min
This is the bright home in which I live, this is where I ask my friends to come, this is where I want to love all the things it has taken me so long to learn to love. - David Whyte, from "The House of Belonging" Virginia Bauman and Iris Bainum-Houle have experienced great success- Virginia as an entrepreneur and founder, Iris as a designer for film and entertainment- and both have also experienced great feelings of otherness. While successful, both felt a call to live and work differently, a cal...
Nov 02, 2016•48 min
Are you courageous enough to look in your blind spots? Alex Blumberg is at a crossroads. His company, Gimlet Media, is producing some of the most successful, interesting podcasts out there with household names such as Reply All, Heavyweight and Startup Podcast. Alex has been working with Jerry as his coach for a while now and has just completed his first 360 Review. In this raw, vulnerable, and courageous episode-- a cross post of Startup Podcast Season 4, Episode 3-- Alex wrestles with the info...
Oct 20, 2016•37 min
360 reviews are a tool that can help leaders make course corrections, supporting both individual growth and the growth of the company. They are an opportunity to hear specifically through the voices of their colleagues how their behavior is making an impact. In this Reboot Extra, Jerry and VC Fred Wilson talk about the importance of 360 reviews, what a well executed 360 review can do for the board-CEO relationship, as well as some suggestions from Fred for CEOs to get the most out of the review ...
Oct 20, 2016•15 min
“I want to think again of dangerous and noble things. I want to be light and frolicsome. I want to be improbable beautiful and afraid of nothing, as though I had wings.” ― Mary Oliver, Owls and Other Fantasies: Poems and Essays Startups are founded with outcome in mind--creating needed change in the world, a successful exit, or most commonly, both. Holding our desired outcomes, or endings, builds the drive for our best work. But when things don’t unfold along the lines or on the trajectory we de...
Oct 07, 2016•41 min
“Development involves giving up a smaller story in order to wake up to a larger story.” - Jean Houston When is the moment at which you become an entrepreneur? Is there a definitive moment or action that makes it official? Sarah Weiler followed her passion to bring creativity and playfulness into the workplace by founding The Power of Uke. Like many entrepreneurs, Sarah is still working a day job to pay her bills as she builds her business. The Power of Uke is growing, gaining clients and billi...
Sep 23, 2016•51 min
“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 grocery...
Sep 05, 2016•40 min
A few weeks ago, we released our first Reboot Extras in collaboration with NextView Venture’s Traction Podcast. Today we’re happy to bring you part 2 of that conversation. In today’s Reboot Extras, NextView’s Jay Acunzo really takes on the role of a skeptic (and plays it quite well). He challenges Dan with a question that we sometimes hear from founders and startup leaders: “Does the soft, interpersonal and relational stuff really matter?” Or the more common form of pushback: “yes, yes, I know I...
Aug 30, 2016•20 min
“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 belong...
Aug 22, 2016•34 min
This is our first Reboot Extra bringing you more Reboot content, ideas, and stories from more Reboot Voices. What happens when you and your co-founder experience conflict or strife but don't address it up front? When something festers and is ready to boil over, how do you bring it back down to a good place? This is Part 1 in a series about the ups and downs of being an entrepreneur in a special collaboration with NextView Venture’s podcast: Traction. Specifically, we'll tackle issues of communic...
Aug 02, 2016•15 min
"Wisdom, then, is a deeper way of knowing. Wisdom is the art of living in rhythm with your soul, your life, and the divine. Wisdom is the way that you learn to decipher the unknown; and the unknown is our closest companion. So wisdom is the art of being courageous and generous with the unknown, of being able to decipher and recognize its treasures." - John O'Donohue from "Anam Cara: A Book of Celtic Wisdom" We are so fortunate to welcome Brad Feld and Fred Wilson back to the Reboot Podcast. Jerr...
Aug 01, 2016•1 hr
"Our capacity to fail is essential to what we are." Costica Bradatan http://opinionator.blogs.nytimes.com/2013/12/15/in-praise-of-failure/ Startups fail. We hear it all the time. Failure is good. We hear that all the time too. But we rarely hear about the pain, the shame, and second guessing. And even worse, we rarely hear about what opportunities may lie for our own growth in something ending beyond the pivot and lessons learned. A startup failing is not proof that something is broken within yo...
Jul 05, 2016•51 min•Ep. 44
There is real suffering out there, suffering that is causing violence. What are some of the causes of the suffering and how might we address those? It's a true honor to welcome entrepreneur, creator, and educator Konda Mason to the podcast for an important and timely conversation with Jerry. This discussion was recorded last week, and we thought it was really important to get this out sooner rather than later, particularly given the events in Orlando. Konda and Jerry address some of the source c...
Jun 21, 2016•51 min
Parker Palmer is a man whose teachings mean so much to us and our work at Reboot, so it's wonderful to welcome him back to the podcast for a new conversation with Jerry. Jerry invited Parker back to explore some important questions: - What is the role of community in responding to a toxic environment? - How do I respond when my leader hasn't done their work and is leading from that place of shadow? - What does it mean when a leader is using organization to resolve unconscious issues? As is alway...
Jun 07, 2016•53 min
"As we let our own light shine, we unconsciously give others permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.” - Marianne Williamson "A Return to Love: Reflections on the Principles of a Course in Miracles” John Guydon is an entrepreneur and speaker who owns his power more than most. He shares with Jerry his story and how he can’t help but tackle big problems like finding missing children and directly discussing and addressing the eco...
May 27, 2016•50 min
“The way to start would be, first, when we feel the tendency to blame, to try to get in touch with what it feels like to be holding on to ourselves so tightly. What does it feel like to blame? How does it feel to reject? What does it feel like to hate? What does it feel like to be righteously indignant?” - Pema Chodron There’s something calming about finding a target for our blame. It’s like in this moment of being lost in a rough sea of chaos and uncertainty, a person to assign the fault is lik...
May 14, 2016•44 min
You do not have to be a fire for every mountain blocking you. you could be a water and soft river your way to freedom too. - options by Nayyirah Waheed Mary Lemmer shares the emotional story of seemingly everything working against her in last 18 months - her body giving in, her relationship ending, her business coming apart, and losing her Dad’s approval. These are physically and emotionally painful experiences, and yet what if they are exactly what she needs? What if she was only waiting for th...
Apr 25, 2016•47 min
“Hurrying and delaying are alike ways of trying to resist the present.” - Alan Watts What’s the conversation you are having with yourself right now? Maybe you’re thinking about an email you wrote earlier, or need to write later. Maybe you’re thinking about an ever-growing todo list, and feeling the anxiety well up within. Or maybe you are doing all of the above. When you stop to really notice, it’s amazing how many conversations we are having internally at any given time. The most important conv...
Apr 11, 2016•45 min
"A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves." - Lao Tzu For leaders the temptation to tell, fix, and even do is so strong. “I know the way,” or “I have the answers,” or “the buck stops with me.” Sometimes it’s impossible to resist the ego boost of providing the answer, giving the fix, telling the way. But what impact does this have on the team, and ourselves? And is it even true? Jerry is joined today by Patr...
Mar 29, 2016•52 min
Do you love yourself enough to listen with the ears of your heart to the other voices of yourself speaking? - Beno Kennedy In today’s special episode Jerry Colonna, Jim Marsden, and Jade Sherer talk about the power and opportunity of time on the land, Jerry’s own experience on a quest, which was guided by Jim and Jade, and why a quest could change your awareness forever. If it terrifies you, you are ready...go apply at reboot.io/quest. Links Apply for the Reboot Quest - http://www.reboot.io/ques...
Mar 21, 2016•41 min
“By cultivating skillful attitudes of mind, we will respond to more and more of life with awareness and wisdom. With steady awareness of the way things are, the perseverance to stay with that awareness, and the willingness to learn from it, we maximize our sense of well-being.” — Steve Armstrong Life happens. It’s full of moments, good and bad, we never thought would happen to us. The magic and opportunity lies in what you do with those moments. Everything is workable if we choose to work with i...
Mar 15, 2016•43 min
“Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakens.” – Carl Jung. "Work is difficulty and drama, a high-stakes game in which our identity, our self-esteem, and our ability to provide are mixed inside us in a volatile, sometimes explosive ways.” That's David Whyte in his incredible book, "Crossing the Unknown Sea: Work as a Pilgrimage of Identity". That volatile, explosive mix is a gift. It presents a tremendous opportun...
Feb 29, 2016•42 min
"Never let the odds keep you from doing what you know in your heart you were meant to do.” - H. Jackson Brown, Jr. Have you ever asked yourself the question: I wonder if we'd be better off with someone else in my role? In this podcast, a listener, Kent Cavender-Bares from Rowbots, comes to Jerry with a similar question: "What if my deep integrity, my commitment to simply telling how it is, is the reason we’re unable to fundraise? Do I even have a Superpower? Wouldn’t Rowbots be further along if ...
Feb 16, 2016•39 min
