The Reboot Podcast

“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 desire, it can be easy to generalize the entirety of our efforts as a failure. Tarikh Korula has founded a number of companies but has yet to achieve an exit. In this episode Jerry and Tarikh discuss how we define failure and how we hold the tragic gap--the space between where we do the work and our often elusive end aspirations. Links Tarikh Korula on Twitter - https://twitter.com/tarikh Robert Irwin: Why Art? - https://youtu.be/5Ac-m3W9fGY "Farewell to Katch" - goo.gl/rx4O1s Parker Palmer on Standing in the Tragic Gap

“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 billings, but Sarah is reluctant to identify as an entrepreneur. In this conversation Jerry and Sarah discuss what’s holding her back from identifying as an entrepreneur and why it’s so hard to shift from living to satisfy what you think is expected of you to what you want and love to do. Links Sarah on Twitter ­ - https://twitter.com/weilersarah Power of Uke on Twitter - https://twitter.com/powerofuke ­ Power of Uke - http://powerofuke.com/

“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 store, he knows how important it is to just keep the business alive and take care of yourself and your family (and to be grateful for that) - to not put your family, your health, yourself at risk. The ambitious path with burnout or the steady, safe path with possible regrets? He has wrestled with this as something he must decide, but what if there isn't a choice? Or what if there is a 3rd option he’s not seeing? Jerry and Amir explore this apparent conflict, talk about his upbringing and his family’s escape from the w

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 should think about that stuff - but I’ll do that when we’re further along and I have more time.” It’s the idea that if I’m not seeing a measurable impact on my bottom line RIGHT NOW by investing in the health of my team and co-founder relationship, then how can it possibly be worth my time? [Spoiler: The best time to do this type of work? Now.] We also explore several big challenges facing founders in an effort to debunk the myth that the “soft stuff” is less important than the “harder” skills we typically hear more a

“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 here, yet.” At the end of the day, we are not that different because we all have a version of that voice, often referred to as impostor syndrome, but the opportunity for all of us lies in how we are with that voice. Jerry and Semil explore that voice, and how shifting his relationship with it can help him be a better man and a better investor - the very things it and he are after. Links Full show notes: - https://www.reboot.io/episode/46-we-are-not-different-with-semil-shah/ Semil Shah on Twitter - https://twitter.com

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 communication, leadership, and mental well-being. Dan Putt of Reboot joins NextView's VP of platform Jay Acunzo for this series. Subscribe to the NextView blog (and podcast): - http://www.nextviewvc.com/blog Sign up for Reboot Podcast and more - http://www.reboot.io/signup Follow the guys on Twitter: - http://www.twitter.com/jayacunzo - http://www.twitter.com/danputt

"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. Jerry, Brad, and Fred have a friendship and history that goes back 20 years, and the wealth of experience between them is truly incredible. In what we hope will be a series of conversations, Fred, Brad, and Jerry share stories from the past, moments where they were pushed to their limits physically and emotionally. They talk about the critical steps they've taken to being an effective and supportive board member and investor, and how the lessons from past painful experiences show up in the values of their firms. We’d love

"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 you. In fact it’s an opening and opportunity to find something new within you and for you. Nick Russell was co-founder and CEO of UK based We are Pop-up. Nick joined Jerry on the very day he handed over the keys and closed up shop on his startup of 3+ years. In this discussion, Jerry and Nick talk about what he’s experiencing now, what he learned and wishes he had done differently, and a surprising path forward for him. It's a path that could be helpful for you in your own transitions. For show notes and Nick’s email add

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 causes of this suffering, this pain, and what opportunities might lie in remembering we’re all in this together. This conversation will challenge you on your privileges and inspire you find new ways of connecting with people from all backgrounds. Links The Whole Person Economy - http://www.thewholepersoneconomy.com/konda-mason/ Konda Mason on Twitter - https://twitter.com/swamikondananda Impact Hub Oakland - https://oakland.impacthub.net Spirit Rock Meditation Center - https://www.spiritrock.org/instructordetails?calend

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 always the case when Parker and Jerry get together, this is a conversation packed full of deep lessons on leadership, the shadow, the importance of relational trust, and the incredible power present in community. This episode will leave you with new profound questions and answers about yourself, your role in your organization, and the power you hold, but may not yet accept. Links Parker Palmer - http://www.couragerenewal.org/parker/ "To Bless the Space Between Us" by John O’Donohue - http://www.amazon.com/Bless-Space-Betwee

"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 economic gap that exists between Black Americans and other communities. Links John Guydon on Twitter ­ - https://twitter.com/Guydon The Lassy Project - http://www.thelassyproject.com/ The Dark Dollar - http://www.imdb.com/title/tt5555176/

“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 like an unsinkable lifeboat to grasp. We climb aboard, take a deep breath, and relax. We do this as individuals, we do this in organizations, we do this as a society. But what incredibly valuable opportunities lie in resisting the urge to assign blame? What might we learn in what didn’t (or did) work if we explore a bit more? Jerry is joined today by author and CTO Dave Zwieback to talk about just that. Dave, in his book “Beyond Blame,” explores the fallacy of blame, how it fails to identify the immense complexity and int

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 this moment to arise? Links The show notes: https://www.reboot.io/episode/39-time-new-choices-mary-lemmer/ Marry Lemmer on Twitter - https://twitter.com/me_lem Foodscape - http://www.myfoodscape.com/ Animas Valley Institute - http://www.animas.org/ Let Your Life Speak by Parker Palmer - http://www.amazon.com/Let-Your-Life-Speak-Listening/dp/0787947350 Pema Chodron - https://en.wikipedia.org/wiki/Pema_Ch%C3%B6dr%C3%B6n Loving-Kindness by Sharon Salzberg - http://www.amazon.com/Lovingkindness-Revolutionary-Happiness-Shambh

“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 conversation we have is with ourselves. What are you saying right now? Congressman Tim Ryan is our guest for Episode 38 of the Reboot Podcast. Tim is a special guy, and not just because he’s a congressman, and not just because he’s from Ohio - though that's pretty great too - but because he’s committed to bringing heart, humanity, mindfulness and a long term focus into a space that doesn’t always welcome it: government. In this conversation (originally recorded in November), Tim shares his journey to mindfulness, his ongoi

"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 Patrick Campbell, co­founder and CEO of Price Intelligently - a bootstrapped company in Boston. Patrick and Jerry explore different leadership styles, the power of “if I die docs,” and how the secret to leadership may not lie in having the right answers, but instead asking the right questions. Links Price Intelligently - http://www.priceintelligently.com/ Price Intelligently on Twitter ­ - https://twitter.com/priceintel Patrick Campbell on Twitter ­ - https://twitter.com/Patticus

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/quest Jim Marsden on Twitter - https://twitter.com/jamarsden Jade Sherer - http://www.earthsecho.com/htm/about.htm Earth’s Echo Explorations - http://www.earthsecho.com/index.htm Animas Valley Soulcraft Program - http://www.animas.org/ Bill Plotkin - http://www.animas.org/about-us/our-founder/ "Soulcraft" by Bill Plotkin - http://www.amazon.com/Soulcraft-Crossing-Mysteries-Nature-Psyche/dp/1577314220

“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 it. And if we choose to let it work us. Our guest today, Richard Hughes-Jones, is choosing to work with it. As a former management consultant, he was always a man with a plan both for himself and others. So it was quite a big leap for him to dive into the entrepreneurial world nearly two years ago, a place where a plan doesn’t guarantee survival. Instead, he was quickly reminded he was part of a bigger struggle, one where plans most certainly do not ensure success or survival: life. In this conversation with Jerry, Rich

“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 opportunity for us to do our own work, our inner work, and further develop our own understanding of self. In our conversation today, Jerry is joined by Henry May, founder and CEO of CoSchool, based in Columbia. Henry comes to Jerry with this very issue: How might the journey of entrepreneurship, specifically his own, open up new opportunities for him to grow? Or said more directly: How might he use his work at Coschool to do the real work on his humanity? CoSchool - http://coschool.co/ CoSchool on Twitter - https://twitter.com

"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 someone else was leading?" Jerry and Kent explore the double edge of a superpower, and how the path through Kent's challenges may lie in a new set of questions: How can I be even more like Kent? How can I embrace my superpower? How can I believe in myself? And why is that so damned important? Links Rowbot - http://rowbot.com/ Rowbot on Twitter - https://twitter.com/rowbotsystems Kent Cavender-Bares on Twitter - https://twitter.com/kbares Parker Palmer - https://en.wikipedia.org/wiki/Parker_Palmer Jerry’s post, “The Cru

“Be yourself; everyone else is already taken.” - Oscar Wilde VC’s Bryce Roberts of OATV and Indie.vc, and Chris Marks of Blue Note Ventures both found the standard issue of the VC world was not a fit for them. They both sought out to set a new path, one that aligned with who they are and what they value. In a conversation with Jerry, and each other, they explore the challenges on their journey, and the potential opportunities they have to better connect with entrepreneurs through those challenges. This conversation may leave you asking yourself: In my own work, what are my values? What are my priorities? What am I wearing today? Links Bryce Roberts on Twitter - https://twitter.com/bryce Chris Marks on Twitter - https://twitter.com/bluenotevc Indie.vc - http://indie.vc Blue Note Ventures - http://bluenotevc.com O’Reilly Alphatech Ventures - http://oatv.com Bryce’s blog post - The Peace Dividend of the Seed Surge - http://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/ Aileen Lee’s article on on Unicorn