The Reboot Podcast

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...

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...

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 T...

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 audi...

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...

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 c...

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 inves...

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 sc...

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 abou...

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 al...

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 hi...

Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joined Jerry for our very first podcast episode in 2014 to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended the first CEO bootcamp and began to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge...

Nancy Lublin, CEO of Crisis Text Line, a non-profit that provides free 24/7 support at your fingertips, is a successful serial social entrepreneur. Previously at Dress for Success and Do Something, her journey as a CEO has been one towards a more authentic and human style of leadership. This journey has informed how she see's her product and the companies she runs. In this candid conversation with...

Throughout his life Adi Mashiach has been a brilliant student, a successful doctor, and has experienced two successful company exits. Along with his wife Mirella, Adi has stepped into the world of VC with the creation of Mesia Ventures. Having just moved to the United States less than a year ago with his family, Adi has started to feel the familiar pangs of belonging trying to break into new circl...

In an entrepreneurial world where being a billionaire is a yardstick for self-worth, and unattainable goals can give us a false sense of responsibility, control and drive, what is the collateral damage to ourselves? As we chase a sense of perfectionism, and measure ourselves against big goals, how do we counteract the sense of self-loathing we can impinge upon ourselves when we fall short of the i...

Sally Spencer-Thomas is a psychologist who found herself in a moment in which she was not prepared when her brother died of suicide. After that significant event in her life, Sally poured much of her life into engaging leaders and finding bold, gap-filling solutions for suicide prevention in schools, workplaces, and communities. Driven by the memory of her brother, Sally dove into her work, and al...

Khe Hy spent 14 years in Financial Services and was successful by all signs, but his work and life felt 'meh.' Something felt disconnected from him as he suited up in the morning and turned off the finance switch in the evening. He opted for a life of more meaning, and started RadReads, a passion project now grown into a community of sorts. But something still didn't feel right for Khe. Even thoug...

Al Doan led his family's fledgling small town quilting shop to a leading online retailer with over 450 employees in just a few short years. To the outside world, this rapid growth established Al has a wildly successful and admired leader, but behind closed doors Al was struggling. He found himself behaving in ways contradictory to his character and struggling to feel happy and content. Sure, he wa...

Simon Cant's path to becoming a VC has been a windy road. Building on a career that includes stints as a lawyer, founder, consultant, director of a non-profit and advisor, he is now an LP in Reinventure, an Australian fintech fund. Alongside his meandering career path, Simon has battled to slow the swing between a strong desire to exert control and an acute awareness of his own need to surrender....

"If we have no peace, it is because we have forgotten that we belong to each other." - Mother Teresa For Bijan Sabet- an investor, US citizen by birth and descendant of Korean and Iranian immigrants- the January 27th Trump administration issue of an executive order banning the entry of residents and refugees from a number of Muslim countries deeply disturbed him for a number of reasons. Recalling...

But little by little, as you left their voices behind, the stars began to burn through the sheets of clouds, and there was a new voice which you slowly recognized as your own, that kept you company as you strode deeper and deeper into the world, determined to do the only thing you could do-- determined to save the only life you could save. - Mary Oliver, The Journey John Guydon first appeared on t...

"To pay attention, this is our endless and proper work." - Mary Oliver In this episode Jerry Colonna is joined by Roshi Joan Halifax, a Buddhist teacher, Zen teacher and anthropologist. Jerry first met Roshi Joan a few years ago when she was presenting on her G.R.A.C.E. model, a process for cultivating compassion in leaders and applicable to anyone looking to cultivate practicing compassion in the...

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." - Hasidi...

Almost all successful entrepreneurs will fail - if not fail, fail, fail, and fail again - on their path to success. Every human being made choices in their lives which they regret, are embarrassed of and have caused them deep shame. What would your life be like if you were known only by the worst thing you had ever done? Catherine Hoke is the founder of Defy Ventures, a program that helps incarcer...

"If we hope to go anywhere or develop ourselves in any way, we can only step from where we are standing. If we don't really know where we are standing... We may only go in circles..." ― John Kabat-Zinn The Reboot podcast was started because we believed that there needed to be an authentic, real conversation about the emotional journey of entrepreneurship. One that included its valleys and not just...