The Reboot Podcast

"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

“Authenticity is the alignment of head, mouth, heart, and feet - thinking, saying, feeling, and doing the same thing - consistently. This builds trust, and followers love leaders they can trust.” - Lance Secretan So many entrepreneurs seek to model their leadership after the high-profile, successful giants. Should I be a leader more like Steve Jobs? How can I be more like Jeff Bezos? How can I be more like Travis from Uber? These are not only questions without answers, they are the wrong questions. The real question is, “Who the fuck are you?” You’re not Steve Jobs. You’re not Jeff Bezos. You’re you. What does the leader within you look like? In today’s conversation, Jerry is joined by Evgeny Shadchnev, Co-founder and CEO of Makers Academy. Ev wrestles with the question of whether it’s possible to scale an organization built around trust, or does success require a leader who governs by fear. Together they discover a more beautiful, more fundamental question --“Who is Evgeny?” In that answer they may find a pa

“Watch carefully the magic that occurs when you give a person just enough comfort to be themselves.” – Atticus Finch There’s a saying: Behind every great man is a great woman. I would add: behind every great entrepreneur is a great friend. The entrepreneurial path simply can’t be traveled alone. So when Jerry asked Kickstarter’s CEO and Co-founder, Yancey Strickler: Who do you turn to? He response was immediate: Ian Hogarth, Co-founder and Chairman of Songkick. We’re grateful to have Yancey and Ian join Jerry in today’s podcast to talk about their friendship, the importance of peer relationships in entrepreneurship, the relief of being heard by those who can empathize with your experience, as well as those who can challenge you from a place of love and deep understanding. Enjoy this discussion with Jerry, Ian Hogarth, and Yancey Strickler. This conversation was recorded in early December, and since then Ian has announced his intention to give up the Co-CEO role at Soundkick and focus on his role at Chairman.

“Life doesn't run away from nobody. Life runs at people.” - Joe Frazier Carrie Barry has had great challenges to overcome, including real struggles at home that forced her to leave at the age of 12 and strike out on her own. She’s proven resilient, stitching the struggles of her past into the fabric of her being and choosing to appreciate and utilize that pain into the work she does today. Carrie Barry is a former Olympic Boxer and entrepreneur who owns and runs a boxing gym in Boulder where people come to break a sweat, get a hug, and learn some valuable life lessons. She also happens to be, in a twist, a boxing coach for 2 of Reboot’s finest: Jerry and Ali. Join Jerry in getting a little coaching, and a lot of inspiration in this conversation with Carrie Barry. Links The Corner Boxing Club - http://www.thecornerboxing.com The Corner Boxing Club on Twitter - https://twitter.com/thecornerboxing

The shadow is everything about ourselves that we do not know or refuse to know, both dark and light. It is the sum total of the positive and negative traits, feelings, beliefs, and potentials we refuse to identify as our own. The shadow is that part of us that is incompatible with who we think we are or are supposed to be. - David Richo Tracy Lawrence, Co-founder and CEO of Chewse, and Jerry talk about authenticity, leading from the heart, and the power of embracing the lost and disowned parts of ourselves. For Tracy, it’s not only about being there for the little girl who was bullied in middle school, but also about owning her very own inner bully. Reclaiming that part of herself will not only impact her approach to the latest company experiment, but it also might affect her own leadership and bring her and her company deeper into alignment. links Chewse - https://www.chewse.com Tracy Lawrence on Twitter https://twitter.com/chewishgirl "Shadow Dance" by David Richo http://www.amazon.com/Shadow-Dance-Liberati

Full notes at Reboot.io/podcast "From caring comes courage." -Lao Tzu It’s wonderful to have the support of so many, to have so many who believe in you. But there is another side to it: the weight and fear of disappointing them. Zoe Weintraub is founder of Opus for Work and is our guest on this episode of the podcast. Zoe and Jerry discuss both the beauty and burden of external expectations, and ultimately find that when you follow the emotion and vulnerability associated with them, they expose your superpower hiding in plain sight. Links Opus for Work - https://www.opusforwork.com Zoe Weintraub on Twitter - https://twitter.com/ZoeWeintraub Opus for Work on Twitter - https://twitter.com/OpusForWork

Full notes at Reboot.io/podcast “...the greatest gift of relationship proves to be that as the result of encountering each other, we are obliged to grow larger than we had planned.” - James Hollis Two co-founders, who refer to each other as business soulmates, have found themselves in that special place of alignment. A place in partnership where they align not just intellectually, not just energetically, not even just at a values level, but at a human level. Jules Pieri (her second time on the show) and her partner Joanne Domeniconi are the co-founders of The Grommet. They join Jerry to talk about the beginning of their partnership, where and how they found alignment at the human level, how it has evolved over time, and the challenges it represents as they scale the business. Links The Grommet - thegrommet.com The Grommet on Twitter - https://twitter.com/TheGrommet Jules Pieri - https://twitter.com/julespieri Joanne Domenic - https://twitter.com/jdomeniconi Fred Wilson - https://en.wikipedia.org/wiki/Fred_Wil