The Reboot Podcast

"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 their attention, the pitfalls of pathological altruism, and how practicing compassion is the cornerstone to wise leadership. Links Roshi Joan Halifax on Twitter - https://twitter.com/jhalifax Upaya Zen Center - https://www.upaya.org When Things Fall Apart - http://a.co/edOQ1a7

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 drive, intuition, or our guiding voice. Regardless of name it pushes us forward. This voice can be our most powerful ally in the pursuit of authentic leadership, or become our greatest enemy when clouded by fear, anxiety, or self-judgment. Most of us equate struggle as a bad or wasted experience. But as we find in this episode, that association is far from the truth. Instead, heartbreak holds our greatest potential to allow true transformation to be possible. Fresh off an $8M round, Matt Munson led his team at Twenty20, a crowd-sourced commercial photography catalogue, in a radical pivot--changing the business model from B2C to B2B. The business seemed to be moving in the right direction, yet Matt began to feel crippling pressure to achieve more growth. This pressure, perhaps better defined as anxiety, quickly became all consuming, permeating through the entire Twenty20 team. It wasn't long until the company had reached another tipping point to survive. With the support of his board, Matt made the difficult decision to layoff nearly 80% of his staff and embrace a new path-- one centered around simplicity, transparency, and embracing the open-hearted warrior within. Links Matt Munson on Twitter - https://twitter.com/mattmuns Twenty20 on Twitter - https://twitter.com/Twenty20app Twenty20 - https://www.twenty20.com How I burned 10 Million Dollars so you don't have to - https://goo.gl/MIpPbW Getting Real - https://gettingreal.io

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 guest) to a prison at the age of 26, Catherine left behind a successful investment career to launch a program to build on what she recognized were valuable entrepreneurial skills - simply applied to illegal businesses. Through the journey of building two wildly successful organizations, Cat had her own personal experience of failure, great shame and having to grant herself grace, and a second chance. Nestled in this conversation about failure, mercy and second chances, is an important second discussion. Joined by investor Brad Feld, this episode also includes a heartfelt reflection on the lottery of birth, acknowledging our own privilege, and what we can do when confronted with these realizations. Links Cat Hoke on Twitter - https://twitter.com/Catherine_Hoke Defy Ventures on Twitter - https://twitter.com/DefyVentures Brad Feld on Twitter - https://twitter.com/bfeld Understanding Privilege – My Experience in Prison - http://feld.com/archives/2016/11/understanding-privilege-experience-prison.html Feld Thoughts - http://feld.com Defy Ventures - https://defyventures.org This former drug dealer is now running a successful gym - https://www.facebook.com/NowThisNews/videos/1127697567320366/ Defy Ventures is helping inmates transform their hustle. - https://www.youtube.com/watch?v=lLoacd_rJsY Episode #43 – The Dharma of Inclusivity – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/

"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 when it happens to them, many entrepreneurs feel totally alone in their experience. Rob Symington is a founder and entrepreneur who experienced a debilitating period of burnout following the launch of his startup, a startup that was inspired by the idea that work could be more fulfilling, less stressful and generally improve people's lives no less. In this conversation, Jerry and Rob discuss his experience, why Rob believes it's so important for him to share it, how he is moving forward, and the fact that the pressure of doing something you passionately believe in can challenge you unlike anything else. Links Escape the City - http://www.escapethecity.org "Email to team on my startup burnout, lessons learned, & finding a new way forwards" - goo.gl/A7vW2w Elle Harrison - http://www.wildcourage.com "It's not you, it's the startup life" - https://medium.com/reboot-leadership-resiliency/its-not-you-it-s-the-startup-life-9290a5183ee9#.kenj6fbw0 "How to avoid burnout" - https://medium.com/reboot-leadership-resiliency/how-to-avoid-burnout-9690601852d8#.syts nzk4h "Love After Love" by Derek Walcott - https://allpoetry.com/Love-After-Love

Join leadership expert Jerry Colonna and renowned Jungian psychoanalyst James Hollis as they dive deep into the concept of the 'shadow.' They discuss how confronting our darker aspects can lead to authentic leadership and personal growth. With insights on emotional awareness, they explore how unresolved issues impact relationships and leadership style. Listen in to discover the power of self-reflection and love in navigating challenges and transforming oneself for the greater good.

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/

Fred Wilson, a seasoned venture capitalist, joins Jerry Colonna to delve into the transformative power of 360 reviews. They discuss how these reviews can enhance board-CEO relationships by providing critical insights into leadership behaviors. Fred highlights the necessity of honest feedback for personal and organizational growth, especially in uncovering blind spots. The conversation emphasizes a holistic approach to leadership evaluation, advocating for the integration of diverse feedback to foster transparency and accountability in management.

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

"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/