The Reboot Podcast

If your closest colleagues were asked to describe the way in which you conducted yourself in your professional career, what might you hope to hear? For Semil Shah, the adjectives he strives for are: dependable, consistent, and reliable. As the founder of Haystack and the father of three young children, Semil takes immense pride in his ability to be seen as available and accountable despite his busy schedule, so much so, that he feels pangs of guilt when he considers his dependability to be slipping. In his second appearance on the Reboot Podcast, Semil works with Jerry to unpack the driving forces that sit behind his need to be seen by his peers in a certain light, and how this need might be limiting his ability to build honest, meaningful connections with those he cares about. Through their conversation, Jerry and Semil explore the root of Semil’s guilt, the power of perception, and beauty of aging with grace. Links Semil Shah on Twitter - https://twitter.com/semil #46 - Hitting a Wall - with Semil Shah - https://www.reboot.io/episode/46-we-are-not-different-with-semil-shah/

In a modern working world which often venerates the ‘grind,’ - long hours and dogged work-ethic - as the dominating model for focused career development, where does that leave room for building families and raising children? In today’s episode, Jerry is joined by Melissa Pasquale, mother of three and Chief Operating Officer at Engain. Together, Melissa and Jerry consider the navigational challenges of being a parent while maintaining a career. Throughout their conversation, Jerry calls on Melissa to consider the fallacy in yearning for the perfect work-life balance; asking us all to consider that our longing to achieve harmony between work and life inevitably imparts feelings of guilt at our inability to do it all (the notion of, "I'm not really working unless I'm panting.”). When we recognize that we can’t absolve the guilt we feel in that nebulous place of balance between work and life, we can pause to consider the deeper question of, “How we are complicit in the need to be ‘good’ enough - at work, as parents, and in life?”

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” — Author Unknown In a culture driven by a series of actions and reactions, how much consideration do we give to the space that lives in the inbetween? When triggered, what might happen if we allow ourselves to pause and tune into our hearts, dropping into what is holding true for us in that moment? In allowing ourselves that brief period of time between stimulus and response, we can learn how to shift our responses from ones of reflexivity to reflectivity - where the resulting interaction emanates respect and trust for ourselves and others. On this week’s episode of the Reboot Podcast, Nicole Glaros, Partner at Techstars, joins Jerry for a thoughtful conversation on perceived awareness, the power of mindfulness, and the inherent resiliency which arises when we master the ability to widen the gap between stimulus and response. Links Nicole Glaros - https://twitter.com/nglaros Founder Fights - https://www.thecornerboxing.com/founder-fights Reboot Bootcamps - https://www.reboot.io/service/bootcamps/

If you’re an avid listener of the Reboot Podcast then you are well acquainted with podcast host and Reboot CEO, Jerry Colonna. You might know that he has the particular gift of making founders cry, and that he possesses the ability to drive authentic conversations with tenderness and compassion. But what makes Jerry such a great coach, leader and friend? For this episode of the podcast, we’re flipping the script on our host, bringing in long time friend and colleague Brad Feld to anchor a conversation in which Jerry recounts the pieces of his past that have shaped his life and led him to where he is today. Together they discuss a multitude of topics, including the power of journaling, the importance of quietness and listening, and how Jerry’s insatiable curiosity drove his career path from journalist, to venture capitalist and now to author and coach. Links Brad Feld on Twitter - https://twitter.com/bfeld

What is it like to be part of a group of peers, who meet regularly, to discuss your most vulnerable challenges that may or may not be related to your business? What does that interaction do for you and your leadership? How does that affect your organizations? In this episode, Al Doan (founder of Missouri Star Quilt Company), Christine Carrillo (CEO of JOANY), Keeley Tillotson (CEO of Wild Friends Foods), and Bryan Birsic (CEO of Wunder) come together to talk with Jerry Colonna about how important their peer groups have been for their personal and professional lives. They talk about the bonds that form and connections made beyond company size and title to a shared humanity, and the importance of space to speak honestly about fears and concerns and struggles, as well as wins. They also touch on how supportive conversations and deep listening fosters accountability at one’s growth edges, self-discovery, and a practice of vulnerability that ripples out into their companies, families, and friendships at large. And, how through their peer groups, they arrive at better versions of themselves and better leaders in their own organizations. Links Reboot Circles/Peer Groups - http://www.Reboot.io/circles

Radical honesty - an open and authentic contribution, which lacks the intention of causing unnecessary pain and suffering, but serves to provide a mirror in which we can clearly reflect on the aspects of ourselves to which we are blind. On this episode of the Reboot Podcast, Jerry is joined by Patty McCord, former chief talent officer of Netflix, renowned for pioneering the use of radical honesty in the workplace. With her new book, "Powerful: Building a Culture of Freedom and Responsibility", Patty aims to clearly define the best path for creating workplace cultures of high performance and profitability. Jerry and Patty consider how the implementation of radical honesty in our organizations serves to forge solid, supportive spaces where workplace safety is no longer defined solely by the assurance of employment, but contains space for team members to feel seen, heard and nourished to grow, where skill sets are broadened, and diverse people with different ways of thinking come together without fear or expectation to judge or be judged. Wouldn’t that be a more powerful way of working? Links #43 – The Dharma of Inclusivity – with Konda Mason - https://www.reboot.io/episode/43-dharma-of-inclusivity-konda-mason/ Patty MCcord - Powerful - https://www.amazon.com/Powerful-Building-Culture-Freedom-Responsibility/dp/1939714095

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

How can you expect to serve others, whether it be customers, portfolio companies, or your organization if your own house is not in order? In this episode that we originally ran last summer, we welcome Brad Feld and Fred Wilson back to the Reboot Podcast. Jerry, Brad, and Fred have a friendship and history that goes back 20 years, and the wealth of experience between them as entrepreneurs and investors is truly incredible. Fred, Brad, and Jerry share stories from the past, moments where they were pushed to their limits physically and emotionally. They talk about the critical steps they’ve taken to being an effective and supportive board member and investor, and how the lessons from past painful experiences show up in the values of their firms. This episode also launches our very practical skills course - Reboot Your Board - a collection of the wisdom from Fred, Jerry and Brad on how to create, build and maintain the best board possible. Learn more at http://www.RebootYourBoard.com Links Reboot Your Board - http://www.RebootYourBoard.com Brad Feld's blog - https://www.feld.com/ Fred Wilson's blog -http://avc.com/

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