What exactly is the Arc of Dysfunction, and why is it important for all organizations, especially startups? From the unhealthy and dysfunctional beginnings to the healthy and dysfunctional apex, Jerry and Ali explore the different stages of this arc and provide insights on how to navigate through them. Discover how understanding and acknowledging this arc can be liberating for leaders and teams, and how it can inform decision-making and company growth. Leave us a review on Apple Podcasts!...

When confronted with the realness of our lives, how we choose to respond matters. It’s no easy feat to turn toward suffering when the world around us gets messy. However, when we open ourselves to love, we create a current of empathy that can lead us, and others, to community, connection, and healing. In this episode, our friend and teacher Sharon Salzberg returns to discuss her latest book, "Real Life: The Journey from Isolation to Openness and Freedom". Sharon reflects on how her COVID...

For individuals stepping more fully into leadership roles, the transition from individual contributor to team leader can bring about a myriad of feelings. What happens when you go from making something to building a team? In this Wisdom for Work, Andy Crissinger & Ray Foote describe the Brightest Bulb Challenge and discuss strategies to help leaders thrive as they transition from maker to leader. They make the case for conducting time and outcome audits and provide guidance for managing...

For leaders, navigating the roller coaster experience of entrepreneurship can be flat-out exhausting. The constant fluctuation of riding highs and surviving lows often leaves little time for reflection, much less appreciation for how far you’ve come. But what if there was a different way? What if you didn’t have to ride the rollercoaster at all? In this episode, Jerry sits down with Jean Smart, founder and CEO of Penelope, a retirement savings platform exclusively for small business owners...

How do you know when it’s time to shut down the business? What does it take to come to this realization as the entrepreneur behind the wheel? In this Operator’s Manual, Ali and Jerry dive into these questions, and touch on the perils of scaling and growth without a drive for profitability. 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...

Being a technical founder poses particular challenges to scaling in your role as CEO. Scaling a company is challenging. Leading through that scale as your role as CEO is also constantly changing adds to the waves of change that a leader must move through on the arc of growth. In this podcast conversation, Andy Crissinger sits down with Evan Drumwright, CEO of Dextrous Robotics. Evan reflects on his transition from academia to entrepreneurship and describes the unique challenges of scaling a...

Content warning: This podcast contains conversations around self-harm and suicidal ideation. The pit of despair is a tough and tricky place. How can you find a way through when it feels like you’re fumbling around in the dark? Mollie West Duffy and Liz Fosslien, authors of Big Feelings: How to Be Okay When Things Are Not Okay, return for another heartfelt conversation with Ali Schultz. In this episode, we define despair and describe how in all of its facets, it is not simply depression....

In this episode of the Reboot Podcast, Jerry sits down with Annahid Dashtgard, a fellow author, activist, and champion for justice, equity, diversity, and inclusivity. The pair discuss Annahid’s latest book, The Bones of Belonging: Finding Wholeness in a White World, which is a poignant collection of essays centered around Annahid’s experiences searching for, and teaching about, belonging in our deeply divided world. Jerry and Annahid delve into the little, insidious, persistent ways we feel...

When markets are volatile and times are turbulent, being a VC can be a nerve-wracking experience. How should a seasoned board member handle themselves when anxieties are high? In this podcast conversation, Jerry sits down with Aileen Lee from Cowboy Ventures and Brad Feld from Foundry Group to discuss how to be an effective board member in stormy times. This conversation offers much to think about if you’re a board member, new VC, or CEO. Leave us a review on Apple Podcasts! Follow our step...

If you work with people, odds are good that hard conversations will be part of your work life. Whether it’s firing an employee or dealing with tension in the executive team or trying to get along with a challenging personality at the office, managing people at any level, and in any scenario, makes difficult conversations inevitable and also essential to working well together. In this podcast, Chris VandenBrink and Andy Crissinger talk about leaning into hard conversations so you can do so...

Ever wonder what happened to building a good ol’ profitable business? Maybe you wonder if there are benefits to bootstrapping in this world of high-growth, venture-backed companies with bloated valuations. In this bite-sized episode of Operator's Manual, Ali sits down with Jerry to discuss the very real benefits of bootstrapping a business. 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: ...

In this Wisdom for Work, Andy Crissinger and Chrystal Bell consider the importance of cultivating lasting practices that link to your values and how these ordinary rituals can support you. Chrystal describes the three key elements of practice: intention, attention, and repetition. The duo shares some simple micro-practices for grounding, centering, and setting intentions, and describes how adopting any of these practices can support you in becoming your best adult self. Leave us a review on...

What is your relationship to anger? For many of us, anger is information. Often, it tells us when an important boundary has been crossed or alerts us when a value we hold dear is being threatened. The challenge of being an adult is finding healthy and generative ways to express our anger without hurting ourselves and others. In this episode, Mollie West Duffy returns to chat with Ali and Chrystal about the many facets of anger and how it has shown up in their own lives. The trio considers the...

In this episode of the Reboot Podcast, Jerry sits down with Koshin Paley Ellison, co-founder the New York Zen Center for Contemplative Care, to talk about his latest book, "Untangled". In his work as a contemplative caregiver, Koshin seeks to better understand the causes of suffering and works to nurture sources of strength such as resilience and compassion. In their time together, Jerry and Koshin contemplate epigenetic trauma and the varying ways our personal suffering can be tangled by the...

We often say trust is one person's assessment of another person's competence, sincerity, and reliability. Accountability is a related concept to trust, but it’s also an inside job. Being accountable means being ready to show up for the work that’s in front of us and be a contributor to the fulfillment of the goal of the whole. In this Wisdom for Work, Coaches Ali Schultz and Virginia Bauman illustrate why the key to accountability is healthy channels of communication and cultures of trust....

Adaptive leadership is the notion that a fixed leadership style isn’t a quick fix or one-stop-shop for all your leadership needs. Adaptive leadership asks you to be keen enough to be with who is in front of you, in any situation, and be able to connect relationally and with what matters. That requires a different skillset than a fixed leadership style. In this Operator’s Manual, Ali and Jerry consider why adaptive leadership is so important for your organization’s leaders, why it matters on...

For our first fresh episode of the 2023 season, Jerry sits down with Lisa Sharon Harper, founder of Freedom Road, and author of the superb book, Fortune: How Race Broke My Family and The World and How to Repair it All. In this compelling conversation, Lisa tells the story of her ancestor, Fortune, as a way to illuminate the effects of race, racism, and Othering. Jerry describes the work he’s done to uncover and understand his own ancestors’ history, and shares how returning to his family’s...

Centering is a practice that brings us into present-moment awareness. Tuning into our breath and the sensations in our body opens up choice, clarity, and an enhanced ability to meet whatever we encounter. In this recording, Chrystal Bell shares a simple practice for feeling into the three planes of the human body - length, width, and depth. May reconnecting to your dignity, belonging, and sufficiency support you in feeling more grounded and centered. Leave us a review on Apple Podcasts!...

What fuels your relationship with work? When you’re not working, what comes up for you? The compulsion to work can arise from various fears and drivers. Whether we are driven by perfectionism, tie our productivity to our worth, or use work to distract ourselves from other powerful demons such as shame, the spell of hustle culture can be hard to shake. In this podcast, we’re sharing Ali’s second conversation with Liz Fosslien and Mollie West Duffy, authors of Big Feelings: How to Be Okay When...

Whether we decide to leave our job, make a career move, or unexpectedly find ourselves without a job, the space between secure positions elicits a lot of things--unprocessed fresh feelings, needs, anxieties, and wondering about next steps. Often, that "next steps" part can feel like an overwhelming mountain. In this episode, Ali hosts a thoughtful conversation with executive recruiter Keith McAllister at Modern Executive Solutions. In their time together, the pair discuss the importance of...

Science tells us that the best time to meditate is often when it’s not easy. Bringing mindfulness and perhaps even a pocket meditation for recentering to the situations when you are getting off-kilter, ungrounded, and upregulated are the moments that create lasting change. In this short clip, Reboot Coach and Facilitator Chrystal Bell leads a short meditation practice designed to support you in finding your center and returning to stillness amidst turbulent times. May it be a grounding...

Chronic illness and chronic pain are topics that can bring up a big mix of interconnected feelings -- uncertainty, burnout, anger, and even despair. They also challenge our perfectionism, make comparisons hard to stop, and can bring up thoughts of shame or even regrets. In this podcast, Ali kicks off the first in a series of conversations with Liz Fosslien and Mollie West Duffy authors of the book Big Feelings: How to Be Okay When Things Are Not Okay. The trio shares openly about what...

In this podcast conversation, Jerry talks with Ian Sanders, author of "365 Ways to Have a Good Day", who found himself at the edge of rediscovery at the beginning of COVID lockdown. Fumbling and longing for ground, he dove into his past by paging through his old journals. Unearthing the stories of his life at that moment reminded him of who he was and what made him tick. His collection of entries from his daily sojourns solidified an understanding of who he was and who he might want to be. In...

Sally Helgesen is a women’s leadership expert who has written many books over the past few decades on women and leadership (How Women Rise, The Female Advantage, The Web of Inclusion). In this episode, Sally and Ali Schultz explore the tendencies and habits that often contribute to women feeling stuck in their leadership roles. Sally describes how women leaders have a different perception, or way of being and seeing, that can make for a markedly unique leadership style and offers models of...

As frequent listeners of the podcast can attest, a well-formed open, honest question can be a catalyst for radical self-inquiry and deep inner work. For Gino Zahnd, the founder of Cozy and Seabright, that question was, “What would I like the people that I work with to know about me that they don’t know?.” Gino, who lives with a rare genetic order called Fabry Disease, shares how one profound question asked at Reboot Bootcamp gave him the courage to share his health struggles with his team and...