The Reboot Podcast

“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 make the unconscious conscious, that we are able to build true compassion for ourselves and others; freeing us to become the leaders we were born to become. James Hollis is a Jungian analyst, author and lecturer whose work has inspired and influenced us at Reboot. In this episode Jerry and James talk in depth about the Jungian concept of shadow, how shadow shows up in leadership, and what we can do once we become aware of our shadow. Links James Hollis’s website - http://www.jameshollis.net "Why Good People Do Bad Things" - goo.gl/cS6kWe Episode #14 Shadow and Leadership - https://www.reboot.io/episode/shadow-and-leadership/ Episode #28 Reclaiming Shadow - https://www.reboot.io/episode/28-reclaiming-the-shadow/ Episode #42 Building Relational Trust - https://www.reboot.io/episode/42-building-relational-trust-parker-palmer

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 call that arose out of the desire to be their full authentic self at all times. This new connection led them to take their own experiences of otherness and transform them to create a sense of belonging, love, acceptance, and community for others. Links Cuties - http://hicuties.com/about/ "The Dharma of Inclusivity" – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/

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 information that is illuminated in his 360 Review. Are they shortcomings to be tucked back under the rug? Or are they opportunities for growth and a deeper understanding of himself as a leader and human? Links Startup Podcast https://gimletmedia.com/show/startup/ Gimlet Media https://gimletmedia.com Alex Blumberg https://twitter.com/abexlumberg

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 process. Links Reboot 360 Reviews - http://www.Reboot.io/360

“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 - http://www.couragerenewal.org/723/

“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 war in Bosnia when he was young, and in this exploration they uncover a new path forward for Amir and the business, one of integration. Links Amir Salihefendic on Twitter - https://twitter.com/amix3k Doist - https://doist.com/ Todoist - https://todoist.com/ Todoist on Twitter - https://twitter.com/Todoist Reboot.io Podcast # 7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin - https://www.reboot.io/episode/depression-and-entrepreneurship/ Parker Palmer - http://www.couragerenewal.org/parker/

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 about. We believe the startup world needs less “how tos” and more self-reflection around the question: “how am I personally showing up?” And this is perhaps the most important question startup founders can ask themselves - after all, one of the biggest reasons startups fail is due to Co-Founder conflict. Subscribe to the NextView blog (and podcast): - http://www.nextviewvc.com/blog Sign up for the Reboot.io Podcast and more - http://www.reboot.io/signup Follow Dan and Jay on Twitter: - http://www.twitter.com/jayacunzo - http://www.twitter.com/danputt

“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/semil Semil Shah's blog - http://blog.semilshah.com/ Getting Things Done by David Allen - https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280 Writing Therapy in Impostor Syndrome - https://en.wikipedia.org/wiki/Impostor_syndrome#Therapy Impostor Syndrome - https://en.wikipedia.org/wiki/Impostor_syndrome Fred Wilson - https://twitter.com/fredwilson

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 to hear your thoughts on this episode, so please check out the show notes at reboot.io/podcast Links Full show notes: https://www.reboot.io/episode/45-whats-love-got-to-do-with-it-fred-wilson-brad-feld Jerry's post on this episode. https://www.reboot.io/whats-love-got/ Fred's first episode of Reboot Podcast https://www.reboot.io/episode/investing-in-trust/ Brad's first episode of Reboot Podcast https://www.reboot.io/episode/live-beyond-compare/ Fred Wilson on Twitter ­ - https://twitter.com/fredwilson Fred’s Blog - http://avc.com Union Square Ventures ­ - https://www.usv.com/ Brad Feld on Twitter ­ - https://twitter.com/bfeld Brad’s Blog ­"Feld Thoughts" ­ - http://www.feld.com/ Foundry Group - http://www.foundrygroup.com/

"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 address go to reboot.io/podcast Links Nicholas Russell on Twitter - https://twitter.com/bettercity We Are Pop Up - https://www.wearepopup.com/ We Are Pop Up on Twitter - https://twitter.com/wearepopup "Let Your Life Speak" by Parker Palmer - https://www.amazon.com/Let-Your-Life-Speak-Listening/dp/0787947350 Pema Chodron - https://en.wikipedia.org/wiki/Pema_Ch%C3%B6dr%C3%B6n

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?calendarinstructorid=54375

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-Between-Us-Blessings/dp/0385522274 Nelson Mandela - https://en.wikipedia.org/wiki/Nelson_Mandela Rosa Parks - https://en.wikipedia.org/wiki/Rosa_Parks "A Ritual to Read to Each Other" by William Stafford - http://williamstafford.org/spoems/pages/ritual.html

"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/