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 and t...
Jul 19, 2023•49 min
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 to sta...
Jul 06, 2023•10 min
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 comp...
Jun 20, 2023•32 min
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. Mollie s...
Jun 07, 2023•52 min
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 pre...
May 19, 2023•53 min•Ep. 165
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 by s...
May 05, 2023•58 min
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 with s...
Apr 18, 2023•26 min
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: Neve...
Apr 04, 2023•9 min
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 Appl...
Mar 22, 2023•24 min
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 po...
Mar 08, 2023•50 min
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 ex...
Feb 28, 2023•45 min•Ep. 163
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. They ...
Feb 14, 2023•31 min
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 an i...
Feb 01, 2023•18 min
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 past ...
Jan 17, 2023•1 hr 3 min•Ep. 162
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! Follow o...
Dec 23, 2022•8 min
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 Thi...
Dec 06, 2022•51 min
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 clear...
Nov 23, 2022•40 min
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 practice ...
Nov 10, 2022•11 min
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 chronicall...
Oct 25, 2022•55 min
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 a ...
Oct 11, 2022•57 min•Ep. 161
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 what ...
Sep 27, 2022•41 min
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 ul...
Aug 30, 2022•48 min•Ep. 161
What can we learn from regret? Regret gives us chance to see things from both sides. The experience we lived through, and the retrospective. Pausing to reflect on what was or has been allows us to see what we’ve learned from the vantage point of where we are now. As Dan Pink asserts in this podcast conversation and in his latest book, "The Power of Regret", regret is a clarifying emotion that is also instructive about how to lead a better life. In this conversation with Jerry, the pair explore t...
Aug 13, 2022•55 min•Ep. 160
When considering collective planning as a team, what are the best practices leaders should adopt and what common pitfalls should they avoid? In this Wisdom for Work, Andy Crissinger and Jerry Colonna share why the actual planning process framework you choose is less important than the interpersonal dynamics among the team. The duo describes how a lack of trust can often undermine even the most thoughtfully designed sessions, and illustrate how collective planning, when executed well, can be a to...
Jul 26, 2022•38 min
When faced with uncertain times and unavoidable challenges, how we show up matters. For some of us, a healthy reaction might be to withdraw and tend to the tender parts of ourselves that need support and care. For others, these crucible moments present an opportunity to lean into the work of our lives and give us the chance to truly discover the work we were born to do. In this episode, Jerry sits down with Andrew Alexseyenko, a Ukrainian entrepreneur and co-founder of KOLO, a nonprofit organiza...
Jul 12, 2022•45 min•Ep. 159
In this conversation, Reboot Coaches Jim Marsden, Marty Janowitz, Ray Foote, and Jerry Colonna sit down to explore career transitions at midlife. Together, they describe their unique midlife experiences and share what was bubbling up for them at the time. They give insight into what helped them get to the other side and acknowledge the importance of honoring endings. Jim walks us through the arc of the Journey of Transformation and shares why we often can’t plan or strategize our way through tra...
Jun 22, 2022•50 min
Laurie Segall is an award-winning journalist, author, and the founder of Dot Dot Dot and D3 Network. In this episode, Laurie sits down with Jerry to chat about her tenure as CNN’s Senior Tech correspondent and gives insight into her experience navigating the world of big media. The pair discuss what it means to “show up” for your life and why slowing down can often be so scary. Laurie reveals how participating in a Reboot Bootcamp forced her to slow down, reflect, and confront some big questions...
Jun 07, 2022•49 min•Ep. 158
What are the benefits of adopting a coaching mindset in your leadership and life? In this podcast Wisdom for Work, Reboot Coaches Andy Crissinger and Chris VandenBrink break down the three fundamental components of coaching - listening, inquiry, and mirroring. The duo describes how incorporating a coach's mentality in your leadership toolkit can foster growth, learning, and creativity within your organization, and provide examples of when and where the leader as coach skillset should be utilized...
May 25, 2022•33 min
In this podcast, Jerry sits down with Chris Remus, Founder of Chainflow, to explore an enormously complex and personal question, “What does it mean to be done?” What unfolds is a thought-provoking conversation around our relationship to work, and why we so often sacrifice our personal happiness in the pursuit of ‘doneness.’ Chris reflects on the ways in which the misalignment between his inner and outer self left him feeling unsafe and sapped his ability to fully tap into his potential. Jerry su...
May 10, 2022•52 min•Ep. 157
Have you ever encountered a person in your life who you couldn’t reason with the same way you could with so many others in your life? Are there some folks that make you act differently, or feel like you walk on eggshells around them? In this podcast, Ali sits down with Megan Hunter, a co-founder of The High Conflict Institute and expert on High Conflict Personalities (also known as HCPs). The pair discuss the five types of HCPs and explore how the HCP brain works differently (and what that means...
Apr 26, 2022•48 min
