The Reboot Podcast

Judson Brewer, Director of Research at the University of Massachusetts Medical School Center for Mindfulness, is a revolutionary thought leader in the field of habit change and the “science of self-mastery.” In this discussion, Judson and Jerry ponder identity, how beliefs about our character might shape the way we show up to meet the world, and the ways in which our perceived identities restrict and confine our sense of self. Links UMass Center for Mindfulness - https://www.umassmed.edu/cfm/ The Craving Mind - https://www.amazon.com/Craving-Mind-Cigarettes-Smartphones-Hooked/dp/0300223242

As leaders, what might happen if we attempted to lead from a place of honesty, equanimity, and compassion? Might we transform our organizations and workplaces into safe oases where our fullest selves emerge, allowing ourselves to step into purpose and the meaningful work of our lives? In this conversation, originally aired on The Interdependence Project Podcast hosted by Tarikh Korula, Jerry and Tarikh tackle the question, “How human can we be as leaders?” We’ve decided this would be a great episode to share with you for the holidays, as we wrap up one year and set out into the fresh tracks of another new season. Links The Interdependence Project Podcast - http://theidproject.org/media/Podcast

On this episode of the Reboot Podcast, Jerry is joined by cinematographer and filmmaker Jeff Orlowski, best known for his critically acclaimed documentary films - Chasing Coral & Chasing Ice. The Emmy Award-winning filmmaker recently received the United Nations' highest environmental honor, the Champions of the Earth award, for his work on spreading powerful environmental messages to a global audience. Believing that film remains one of the best mediums for effecting positive change, Jeff founded Exposure Labs. Self-described as an ‘impact production company,’ their mission focuses on utilizing visceral, honest storytelling to enact change and enable open conversations on tough subjects. In this conversation, Jeff discusses the parallels of filmmaking and serial entrepreneurship, reflecting on how his new projects can generate the same feelings of uncertainty, thrill, and fear that often arise in early-stage startups. Jeff shares his journey into filmmaking and how he sees himself first and foremost as a problem solver. Together, Jerry and Jeff hold a dialogue on Purpose, pondering its elusiveness, why we chase it and the reasons we often seek our purpose in the ‘wrong’ places.

Matt Tara is the CEO of an e-commerce fashion company that failed, but is still very much alive in his head. As a former venture capitalist in private equity, Matt thought he’d be swift to success as an entrepreneur. When the road turned rocky, Matt was forced to put his company to rest, and he was left with many multifaceted feelings -- among them: failure, grief, and the understanding of what it means when an entrepreneur says “this is hard.” Most of all, he felt abandoned and at a loss for peers who could really listen to him. In this conversation, Jerry helps Matt conceptualize the latest speed bump in his life. They begin to unpack all of the gifts and lessons received from this experience and propose tactics for keeping Matt’s inner critic at bay as he considers what’s next.

Bobby Brannigan, CEO of Mercato, has built his second company into a steadily growing business in a hard market with narrow margins. While the company is growing strong, he longs for the excitement of his first startup - which he remembers as a thrilling success. In this conversation, Jerry asks Bobby to consider what having high-risk stakes means for him, and how he can connect to that sense of confidence and aliveness in other aspects of his life. They also acknowledge that patience and persistence are integral to affecting the change Bobby wants to see in the market he cares about - and how it’s not so easy being patient when you know where you want to get to. Links Mercato - http://www.mercato.com

In this engaging discussion, venture capitalist Brad Feld shares insights from his impressive career alongside fellow investor Fred Wilson. They reflect on their 20-year friendship and the vital role of a well-structured board in business success. The duo emphasizes the importance of prioritizing company well-being over personal interests and navigating the emotional challenges investors face. They also explore how empathy and trust are fundamental for creating strong organizational values, illustrating these points with personal anecdotes and lessons learned from past struggles.

Erin Frey and Ti Zhao are the co-founders of Kip - an app which aids in locating a quality therapist and helps you measure your progress. In this episode they sit down with Jerry to talk about what makes them tick and how they work together as leaders. This includes emotional literacy and helping each other regulate when tough issues arise. What does your cofounder (or partner) do when they are scared, angry, sad, triggered? Do you know what they need in that moment? Making time to discover the operating instructions for your partner solidifies not only your communication with each other, but also, as Jerry notes, tending to good communication sets culture, direction, and creates the conditions in which raising capital is enhanced. Links Kip - Smarter Therapy - https://www.hellokip.com/ Erin Frey - https://twitter.com/erinfrey Ti Zhao - https://twitter.com/ti_am_i

Jason Jacobs, former founder of Runkeeper, pursued being an entrepreneur with passion and maniacal focus. After starting Runkeeper at age 30, he now finds himself on the other side at 41 post-acquisition, finally reflecting back on the last decade of work. Knowing that he wants to experience building the next company differently, in a more healthy way and with more joy, Jason talks with Jerry about the conundrum of getting lost and consumed in the fire of work. And, how to dive into his work without being so unhappy. At this mid-life juncture of Jason’s time before his “Second Act,” they take the opportunity to pause and unpack deeply held notions about how work must be, what success is, and what it means to lead a fulfilling life. Links "The Problem of the Potter" - https://www.themonsterinyourhead.com/2010/01/31/disappearing-into-the-fire/

Ben Rubin and Dan Harris have found themselves as unlikely cofounders in 10% Happier, which came together when Ben’s company, Change Collective, underwent a successful pivot into a new focus, a new name, and a new co-founder. At the time, Ben stared down his biggest fears of failure - that of creating another “smoking black hole” - only to shift the company, raise money and relaunch the product all in a short two month span, pulling off what their investor Matt Harris called “a triple lindy.” Almost two years later, 10% Happier is among the top mindfulness and guided meditation apps. In this episode, Ben and Dan open up to Jerry about what it’s like being cofounders. They shed light on how their mutual anxieties affect their relationship and their company. Links http://www.10percenthappier.com/Reboot

Adeesh Agarwal is an architect who has worked in real estate, med-tech, and had started and managed his own design firm, which recently closed it’s doors. He finds himself soul searching at 40 years old looking back at the choices he’s made to have a job and be a responsible caretaker for his family. He struggles with finding work that isn’t soul-sucking, that creates safety and opportunity for his family, and wanting to have a sense of stability and sense of progress in his life. As he looks at his life and the choices ahead, he asks: Who am I? What are my strengths? Jerry and Adeesh talk about how there’s a much deeper existential question behind those questions, and how a better question is to ask: What am I made of? And how do the aspects of me come together in ways that I am proud of and ways that hold me back?