The Reboot Podcast

For leaders, when our aspirations and passions align, a crucible is formed from which creativity and productivity stem. At this point in our entrepreneurial journeys we might burn a little brighter, and our way forward feels undeniably palpable. Riding the tide, we may begin to feel ourselves cresting the wave and entering a place where the water becomes muddy and our paths unclear. We’ve entered the dip, and suddenly find ourselves in a quit it or stick with it moment where we must determine how we want to walk through this world. On this episode of the Reboot Podcast, Jerry is joined by friend, entrepreneur, author and speaker, Seth Godin. In this conversation, Seth and Jerry seek to tackle the dip, asking us to consider what is actually happening when it occurs, reminding us of the importance of finding our allies during this time, and how living in the tension of unknowing can actually be the catalyst for attuning our understanding to the most authentic way forward – in our companies, our relationships, and on our own personal paths. Links Pema Chodron’s - Comfortable with Uncertainty - https://www.amazon.com/Comfortable-Uncertainty-Cultivating-Fearlessness-Compassion/dp/1590300785 Seth Godin’s - The Dip - https://www.amazon.com/Dip-Little-Book-Teaches-Stick/dp/1591841666 #33 - Do I Event Have a Superpower - with Kent Cavender-Bares - https://www.reboot.io/episode/33-do-you-have-a-superpower/ #73 - Jeff Orlowski - Chasing Purpose: - https://www.reboot.io/episode/73-chasing-purpose-jeff-orlowski/ Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

For leaders in the modern world, dodging the constant bombardment of projected successes that others display across various media outlets can be exhausting. Comparing ourselves to others can lead to an overwhelming sense of inadequacy, which often ripples out to thoughts of insecurity about our work, our relationships, and the way we are perceived by our peers. As Theodore Roosevelt so poignantly observed, “Comparison is the thief of joy.” By allowing our gaze to become so outwardly attuned, we create an internal roadblock against finding peace and equanimity within our own lives. On this episode of the Reboot Podcast, Jerry is joined by longtime friend and self-described serial entrepreneur, Steve Kane. In this discussion, Steve comes to Jerry with the lingering question, “When do we begin to know when enough is enough?” Together, they explore the pivotal role Steve’s father played in molding the baseline for determining his “enough,” and how his own radical self-inquiry supported Steve in making a difficult decision during the successful exit of his third startup, Gamesville. As they ponder the question of ‘enough,’ Jerry and Steve touch on the ways in which we, as humans, yearn for safety, love and belonging, and how, ultimately, our ability to expand our awareness of ‘enough’ is an act of continuous practice, one which allows us to take stock of our lives at any moment and truly consider, “When is enough, enough for me?” Links Steve Kane on Twitter - https://twitter.com/stevenkane Reboot Bootcamp - reboot.io/bootcamps Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: - How To: Leave a Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

For many leaders, particularly entrepreneurs striving to build a vision, the experience of rejection hits close to home; oftentimes, it can feel as though there’s been a dismissal of our very soul. When faced with the fallout of rejection our initial response may be to thicken our skin or steel our reserve, building a wall behind which we suppress our sadness, our hurt, our tender selves. However, for all of us, another opportunity exists, one of compassion but also of strength; the opportunity to meet rejection as a warrior. On this episode of the podcast, Jerry is joined by Grace Belangia, Community Development Strategist for CONima and the Executive Director and Founding Member of the Clubhouse, a collaborative and innovative community for entrepreneurs. This past fall, Grace reached out to the Reboot Podcast looking for support navigating her feelings around rejection. In this conversation, Jerry works with Grace to uncover the root of her fears about rejection and how its threat may actually be the driving force that allowed her to discover her life’s passions. With Jerry’s guidance, Grace is encouraged to take an open-hearted stance toward rejection and reminded that standing as a warrior requires that we release ourselves from the notion that our self-worth is tied to the acceptance of people we deem powerful and influential. Jerry affirms that as we exist, we are lovable and whole, regardless of our perceived failures, and that ultimately, we, and we alone, hold the to key to determining our worth and belonging. Leave us a review on Itunes! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Your iPhone: www.reboot.io/leave-itunes-review-via-iphone/ Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases. www.Reboot.io/signup

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

“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 interdependency of the world around us, and the real cost of rapidly assigning fault. If we pause and explore, we may just find that blame often prevents us from doing the very thing we want most - to learn and to grow. Links Dave Zwieback on Twitter - https://twitter.com/mindweather Beyond Blame by Dave Zwieback - http://www.amazon.com/Beyond-Blame-Learning-Failure-Success/dp/1491906413 The Five Dysfunctions of a Team by Patrick Lencioni - http://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756 Daniel Kahneman - https://en.wikipedia.org/wiki/Daniel_Kahneman John Allspaw - https://twitter.com/allspaw Truth and Reconciliation Movement - https://en.wikipedia.org/wiki/Truth_and_reconciliation_commission#The_South_African_TRC_and_after