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 ...
Oct 06, 2017•51 min
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 wit...
Sep 21, 2017•46 min
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." Al...
Aug 29, 2017•1 hr 4 min
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...
Aug 17, 2017•1 hr
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 that could have destroyed his business. In this conversation, Jerry and Derek talk about how in our ...
Jul 24, 2017•52 min
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 Jerry Colonna, Nancy talks about what it means to be a social entrepreneur and being human centric ...
Jul 13, 2017•48 min
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 circles and begin building a new venture fund. Recently, Adi has begun to wonder how to live his passion ...
Jun 22, 2017•43 min
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 images we're up holding? In this conversation, Jerry sits down with Sharon Salzberg, on her new book ...
Jun 06, 2017•43 min
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 along the way, she found a community and purpose around her brother's legacy. Over the last 14 years, ...
May 25, 2017•1 hr 1 min
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 though he preached a lot about what's important, he found that a hard talk to walk and instead found hims...
May 04, 2017•54 min
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 was killing it as an online quilting retailer, but was this really what he wanted his life to be? Reco...
Apr 20, 2017•39 min
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. In this conversation Jerry leads Simon to remember that there is no such thing as a perfect surrende...
Apr 06, 2017•41 min
"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 his own early experience of being othered as the child of an Iranian immigrant during the Iran Hosta...
Mar 23, 2017•38 min
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 the podcast in Episode #41: Are You Afraid of Your Own Power. It has been just under a year since tha...
Mar 09, 2017•45 min
"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 their lives. Throughout the episode Jerry and Roshi Joan discuss how leaders can learn to best allocate...
Feb 16, 2017•45 min
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." - Hasidic Tale, as told by Parker Palmer Every entrepreneur hears the call of an inner voice. We may call it...
Jan 26, 2017•49 min
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 incarcerated individuals transform their hustle to entrepreneurial ventures. Following a chance visit (as a ...
Jan 19, 2017•1 hr 3 min
"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 its peaks. One in three entrepreneurs will struggle with depression or burnout in their career, yet...
Dec 15, 2016•51 min
"One does not become enlightened by imagining figures of light, but by making the darkness conscious. The latter procedure, however, is disagreeable and therefore not popular." - C.G. Jung Exploring one's shadow is no easy undertaking. The idea of getting to know what Jung referred to as, "That which I do not wish to be" is rarely considered an exciting prospect. Yet we implore all leaders to be courageous and get to know and learn to work with their shadow. It is only when we do the work to mak...
Nov 23, 2016•43 min
This is the bright home in which I live, this is where I ask my friends to come, this is where I want to love all the things it has taken me so long to learn to love. - David Whyte, from "The House of Belonging" Virginia Bauman and Iris Bainum-Houle have experienced great success- Virginia as an entrepreneur and founder, Iris as a designer for film and entertainment- and both have also experienced great feelings of otherness. While successful, both felt a call to live and work differently, a cal...
Nov 02, 2016•48 min
Are you courageous enough to look in your blind spots? Alex Blumberg is at a crossroads. His company, Gimlet Media, is producing some of the most successful, interesting podcasts out there with household names such as Reply All, Heavyweight and Startup Podcast. Alex has been working with Jerry as his coach for a while now and has just completed his first 360 Review. In this raw, vulnerable, and courageous episode-- a cross post of Startup Podcast Season 4, Episode 3-- Alex wrestles with the info...
Oct 20, 2016•37 min
360 reviews are a tool that can help leaders make course corrections, supporting both individual growth and the growth of the company. They are an opportunity to hear specifically through the voices of their colleagues how their behavior is making an impact. In this Reboot Extra, Jerry and VC Fred Wilson talk about the importance of 360 reviews, what a well executed 360 review can do for the board-CEO relationship, as well as some suggestions from Fred for CEOs to get the most out of the review ...
Oct 20, 2016•15 min
"I want to think again of dangerous and noble things. I want to be light and frolicsome. I want to be improbable beautiful and afraid of nothing, as though I had wings." ― Mary Oliver, Owls and Other Fantasies: Poems and Essays Startups are founded with outcome in mind--creating needed change in the world, a successful exit, or most commonly, both. Holding our desired outcomes, or endings, builds the drive for our best work. But when things don't unfold along the lines or on the trajectory we de...
Oct 07, 2016•41 min
"Development involves giving up a smaller story in order to wake up to a larger story." - Jean Houston When is the moment at which you become an entrepreneur? Is there a definitive moment or action that makes it official? Sarah Weiler followed her passion to bring creativity and playfulness into the workplace by founding The Power of Uke. Like many entrepreneurs, Sarah is still working a day job to pay her bills as she builds her business. The Power of Uke is growing, gaining clients and billi...
Sep 23, 2016•51 min
"I am not what has happened to me, I am what I choose to become." - Carl Jung Amir Salihefendic, the founder and CEO of Doist, is the creator of the powerful and popular productivity tool, Todoist (which is awesome). He comes to Jerry feeling torn between two seemingly different directions for his business. On one side, he feels the ambition to do big, world changing things and to be on every smartphone and desktop. But on the other side, as the son of entrepreneurial parents who owned a grocery...
Sep 05, 2016•40 min
A few weeks ago, we released our first Reboot Extras in collaboration with NextView Venture's Traction Podcast. Today we're happy to bring you part 2 of that conversation. In today's Reboot Extras, NextView's Jay Acunzo really takes on the role of a skeptic (and plays it quite well). He challenges Dan with a question that we sometimes hear from founders and startup leaders: "Does the soft, interpersonal and relational stuff really matter?" Or the more common form of pushback: "yes, yes, I know I...
Aug 30, 2016•20 min
"Most of us have two lives. The life we live, and the unlived life within us. Between the two stands Resistance." ― Steven Pressfield "The War of Art" Semil Shah has done remarkably well as a one-man shop, but he is wrestling with the challenges of growing his business and being with his growing family of 5, while continuing to grow himself. Adding to those challenges, there's also a sneaky voice for him, one that can drive him and also hold him back, one that is saying to him: "You don't belong...
Aug 22, 2016•34 min
This is our first Reboot Extra bringing you more Reboot content, ideas, and stories from more Reboot Voices. What happens when you and your co-founder experience conflict or strife but don't address it up front? When something festers and is ready to boil over, how do you bring it back down to a good place? This is Part 1 in a series about the ups and downs of being an entrepreneur in a special collaboration with NextView Venture's podcast: Traction. Specifically, we'll tackle issues of communic...
Aug 02, 2016•15 min
"Wisdom, then, is a deeper way of knowing. Wisdom is the art of living in rhythm with your soul, your life, and the divine. Wisdom is the way that you learn to decipher the unknown; and the unknown is our closest companion. So wisdom is the art of being courageous and generous with the unknown, of being able to decipher and recognize its treasures." - John O'Donohue from "Anam Cara: A Book of Celtic Wisdom" We are so fortunate to welcome Brad Feld and Fred Wilson back to the Reboot Podcast. Jerr...
Aug 01, 2016•1 hr
"Our capacity to fail is essential to what we are." Costica Bradatan http://opinionator.blogs.nytimes.com/2013/12/15/in-praise-of-failure/ Startups fail. We hear it all the time. Failure is good. We hear that all the time too. But we rarely hear about the pain, the shame, and second guessing. And even worse, we rarely hear about what opportunities may lie for our own growth in something ending beyond the pivot and lessons learned. A startup failing is not proof that something is broken within yo...
Jul 05, 2016•51 min•Ep. 44
