“Be yourself; everyone else is already taken.” - Oscar Wilde VC’s Bryce Roberts of OATV and Indie.vc, and Chris Marks of Blue Note Ventures both found the standard issue of the VC world was not a fit for them. They both sought out to set a new path, one that aligned with who they are and what they value. In a conversation with Jerry, and each other, they explore the challenges on their journey, and the potential opportunities they have to better connect with entrepreneurs through those challenge...
Feb 01, 2016•51 min
“Authenticity is the alignment of head, mouth, heart, and feet - thinking, saying, feeling, and doing the same thing - consistently. This builds trust, and followers love leaders they can trust.” - Lance Secretan So many entrepreneurs seek to model their leadership after the high-profile, successful giants. Should I be a leader more like Steve Jobs? How can I be more like Jeff Bezos? How can I be more like Travis from Uber? These are not only questions without answers, they are the wrong questio...
Jan 18, 2016•47 min
“Watch carefully the magic that occurs when you give a person just enough comfort to be themselves.” – Atticus Finch There’s a saying: Behind every great man is a great woman. I would add: behind every great entrepreneur is a great friend. The entrepreneurial path simply can’t be traveled alone. So when Jerry asked Kickstarter’s CEO and Co-founder, Yancey Strickler: Who do you turn to? He response was immediate: Ian Hogarth, Co-founder and Chairman of Songkick. We’re grateful to have Yancey and ...
Jan 02, 2016•45 min
“Life doesn't run away from nobody. Life runs at people.” - Joe Frazier Carrie Barry has had great challenges to overcome, including real struggles at home that forced her to leave at the age of 12 and strike out on her own. She’s proven resilient, stitching the struggles of her past into the fabric of her being and choosing to appreciate and utilize that pain into the work she does today. Carrie Barry is a former Olympic Boxer and entrepreneur who owns and runs a boxing gym in Boulder where peo...
Dec 16, 2015•50 min
The shadow is everything about ourselves that we do not know or refuse to know, both dark and light. It is the sum total of the positive and negative traits, feelings, beliefs, and potentials we refuse to identify as our own. The shadow is that part of us that is incompatible with who we think we are or are supposed to be. - David Richo Tracy Lawrence, Co-founder and CEO of Chewse, and Jerry talk about authenticity, leading from the heart, and the power of embracing the lost and disowned parts o...
Nov 29, 2015•55 min
Full notes at Reboot.io/podcast "From caring comes courage." -Lao Tzu It’s wonderful to have the support of so many, to have so many who believe in you. But there is another side to it: the weight and fear of disappointing them. Zoe Weintraub is founder of Opus for Work and is our guest on this episode of the podcast. Zoe and Jerry discuss both the beauty and burden of external expectations, and ultimately find that when you follow the emotion and vulnerability associated with them, they expose ...
Nov 08, 2015•39 min•Ep. 27
Full notes at Reboot.io/podcast “...the greatest gift of relationship proves to be that as the result of encountering each other, we are obliged to grow larger than we had planned.” - James Hollis Two co-founders, who refer to each other as business soulmates, have found themselves in that special place of alignment. A place in partnership where they align not just intellectually, not just energetically, not even just at a values level, but at a human level. Jules Pieri (her second time on the s...
Oct 24, 2015•1 hr•Ep. 26
Full notes at Reboot.io/podcast "Can we live beyond compare?" -David Richo Brad Feld is an investor, entrepreneur, and blogger who has been supporting entrepreneurs all over the world since 1987. Brad has also been a great Reboot supporter and teacher. In this conversation, Brad joins Jerry Colonna to talk about VC’s as Dungeons and Dragons characters, Brad’s evolved investment criteria, and the single best piece of advice Brad offered to Jerry that changed his career. Links Feld Thoughts Blog -...
Oct 11, 2015•50 min•Ep. 25
Full notes at Reboot.io/podcast See Hugh's special Reboot inspired cartoons on the show notes linked above. Hugh MacLeod has tapped into his own heart and his own woundedness so that he can speak to the hearts of people and organizations to inspire, to question, to laugh and to grow. Hugh joins Jerry in this episode of The Reboot Podcast to discuss how how he got his start, what motivates leaders, and how to work (and lead) from the heart. (Hint: often the "how" lies in identifying our own wound...
Sep 19, 2015•28 min•Ep. 24
Full notes at Reboot.io/podcast "With a little more care, a little more courage, and, above all, a little more soul, our lives can be so easily discovered and celebrated in work, and not, as now, squandered and lost in its shadow.” - David Whyte Sometimes we spend so much time looking at where we aren’t or where others have gone that we don’t fully appreciate where we are and how much we’ve grown on the journey. A year ago today, Reboot didn’t have a podcast. A year ago today, Sherman Lee was st...
Sep 07, 2015•42 min•Ep. 23
We’re often in (or feel we’re in) uncharted waters - a place where making things up as we go is a necessity. Feeling lost in those places can be anxiety-inducing. We feel incompetent. We feel shameful. We can end up feeling that everyone has figured it out but me. But how true is that, really? And perhaps the better question--how can owning my own anxiety in these areas help me step more fully into my authentic self and even increase my capacity for happiness? We are honored to welcome one of ou...
Aug 23, 2015•42 min•Ep. 22
"I would love to live like a river flows, carried by the surprise of its own unfolding." John O'Donohue The ups and downs, the hills and valleys, the ebb and flow, the rollercoaster - there are many ways to describe the emotional journey of being an entrepreneur. There are also many, many ways we try to straighten out and control the journey. We look to “optimize” for the peaks and minimize the valleys. But what if we’re looking at it all wrong? In this episode of the Reboot podcast, Jerry is jo...
Aug 12, 2015•44 min•Ep. 21
full show notes: reboot.io/podcast "Everyone thinks of changing the world, but no one thinks of changing himself." - Leo Tolstoy It sounds so obvious, perhaps even tongue in cheek, but it also seems to be forgotten enough that it needs to be said aloud again: Investors are human too. They, like the entrepreneurs they back, can ride the rollercoaster of emotions that often come with starting a company. In this episode Jerry Colonna is joined by Bijan Sabet of Spark Capital to explore some of the ...
Jul 25, 2015•42 min•Ep. 20
For more go to reboot.io/podcast What’s it like to find your path of authentic service in the world? What if you could use the pain of the past, a pain of not knowing where you fit in, of not knowing where you belong to propel you toward work that makes a difference? What if you could create a place of belonging? Well, it might look a lot like what Tanisha Robinson is building with Print Syndicate. Started just 2.5 years ago with 8 people, Print Syndicate now has over 140 employees and will gene...
Jun 21, 2015•42 min•Ep. 19
see more at: Fear is a familiar and powerful co-founder in startups. We do our best to quiet it, shut it down, deny it. Perhaps our biggest struggle is simply acknowledging it. But what if you not only acknowledged your fear, but leaned into it? What if you let go of your own hope to control things, and go back to building and leading from a place of love? Jules Pierri, cofounder and ceo of the product launch platform the Grommet, has done just that for her growing team of 55 employees. In this ...
May 30, 2015•43 min•Ep. 18
see more at: “A good half of the art of living is resilience.” ― Alain de Botton Nigel Sharp, our first returning podcast guest, is wrestling with one of the hardest question any entrepreneur can ask themselves: Am I being stubborn or resilient? Shouldering the hope and opportunity of improving a country through his organization and carrying a real concern for his own team, he stares down an empty company bank account, wrestling with a deep confusion whether he should push on or move on. Jerry a...
May 17, 2015•38 min•Ep. 17
see more at: What if your agreements with partners and co-workers were more focused on the characteristics of how you come together, related to one another, and work together, instead of what happens when sh*t hits the fan? What if your co-founder agreement came from a place of hope instead of fear? Zelle Nelson and Maureen McCarthy are co-founders of The Center For Collaborative Awareness and our guests for today’s conversation. They’ve created a collaborative process called “The Blueprint of W...
May 01, 2015•32 min•Ep. 16
For full video visit: JW Player has come a long way. The JW player and platform is now used by over 2.5 million publishers and 20% of the fortune 1,000 companies. Each month about 1 billion people watch video on their platform. Behind those numbers are real people--including three co-founders who, over the last eight years, have experienced their own profound personal growth and leadership transformations. In a special first video episode, only fitting for the co-founders of one of the world’s l...
Apr 05, 2015•1 hr 2 min•Ep. 15
Full notes and more: reboot.io/podcast Who are you? What do you believe to be true? What do you bring consciously to the world? And, even more interesting, what do you bring unconsciously to your work, your organization, your relationships? How does that which you have either denied about yourself, or feel uncomfortable about, shape your life, either positively or negatively? What lies in this unseen shadow? And why is it important for you to explore? The work of today’s guest shows up in just a...
Mar 19, 2015•59 min•Ep. 14
To have a firm persuasion, to set out boldly in our work, is to make a pilgrimage of our labors, to understand that the consummation of work lies not only in what we have done but who we become while accomplishing the task. -David Whyte - Crossing the Unknown Sea: Work as a Pilgrimage of Identity Show notes (and more): reboot.io/podcast In today’s conversation Jerry is joined by Ben Rubin - Cofounder and CEO of Change Collective - an organization itself that is set on helping people make positiv...
Mar 04, 2015•46 min•Ep. 13
Difficulties are just things to overcome, after all. -- Sir. Ernest Shackleton Ben Saunders knows very well the ups and downs that come with attempting to do something groundbreaking. Like so many entrepreneurs, he struggled with the challenges of being an effective leader, and faced the pain of fundraising or not meeting payroll. But Ben’s end goal was a bit different. He’s a polar explorer. Between October 2013 and February 2014, he and his companion Tarka broke the record for the longest ever...
Feb 19, 2015•54 min•Ep. 12
“Consciousness is so turbulent” - Emily Horn Vincent Horn is a mind hacker & Buddhist geek. He has been practicing meditation intensively since his freshman year in college. In 2006, Vincent co-founded Buddhist Geeks, which has gone on to become one of today's most important venues for exploring Buddhist thought & practice in the 21st century. Buddhist Geeks has been featured on the pages of the Los Angeles Times, The Guardian, Tricycle, and The Atlantic. Vincent was also honored to be part of W...
Feb 09, 2015•55 min•Ep. 11
“I have not failed. I've just found 10,000 ways that won't work.” ― Thomas A. Edison Most startups fail. We all know this as much as we try to forget it. The absolute hardest, hardest question an entrepreneur can ask themselves is: When do you know it’s over? In the first of two conversations in this episode, we are joined by Derek Bereit, CEO and Co-Founder of Symptomly, who is staring down the end of his runway and wrestling with this very question. In a second conversation we hear from Beth M...
Jan 22, 2015•40 min•Ep. 10
Be Without Deception. Being without deception is an extension of telling the truth: it is based on being truthful with yourself. When you have a sense of trusting your own existence, then what you communicate to other people is genuine and trustworthy. -Chogyam Trungpa Rinpoche In 19 years of friendship and partnership in the startup world, Fred Wilson and Jerry Colonna have seen just about everything. In this conversation they share some stories from the Flatiron Partnership days, what makes a ...
Jan 13, 2015•43 min•Ep. 9
“Knowing yourself is the beginning of all wisdom.” ― Aristotle For notes and more: Entrepreneur and CEO Blaine Vess has an impressive story. Studymode, the company he helped start and bootstrap from his dorm room almost 16 years ago, now has 30 employees and sees between 60-90M visitors a month. It’s rare to find 15 year old bootstrapped companies. It’s rare to have the same CEO for 15 years as Blaine has been. But last year, Blaine wanted more for his company and himself. He wanted to know how ...
Jan 05, 2015•31 min•Ep. 8
After years of rapid growth and expansion, followed by a serious year of depression, Rand Fishkin, founder and former CEO of Moz, found himself in a room surrounded by VC backed CEO’s and entrepreneurs where the question was posed: “How many of you struggle seriously with depression or severe anxiety or emotional issues?” He watched almost every person raise their hand. It’s shocking how universal depression is in startups. For anyone struggling with depression, it’s helpful to know you’re not a...
Dec 10, 2014•44 min•Ep. 7
Do you have an innate desire to make people happy? And does that desire at times cause you to at hold back the truth, out of fear of perhaps hurting others and yourself? Carm Huntress is the CEO of RxReview, a company solving a big problem with big data - overspending on prescription drugs. The company started in January 2012 and is growing beyond it’s 11 employees. Carm realizes his nature as a people pleaser affects his leadership in detrimental ways. In this episode, Jerry and Carm unpack wha...
Nov 26, 2014•37 min•Ep. 6
Joseph Chura is the founder and CEO of 2 startups that employ nearly a combined 100 people, yet he feels a constant drive for more. In this conversation with Jerry, Joseph shares his struggles to be present, especially at home with his wife and kids and they explore the question: Why is the drive to succeed, the itch to not sit still, so strong? Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-co...
Nov 11, 2014•57 min•Ep. 5
How can you save a business from the brink of bankruptcy and grow it 2,000% in 10 years, and yet feel like it could all go away in any given moment? Or face the fear, the weight, that you must be chief breadwinner...for you, your family, your co-founder and team’s family as well? Fear is pervasive in our lives, and in the crazy world of startups and entrepreneurship it is an always present participant. In this episode, we have two entrepreneurs dealing with two different and yet similar fears, f...
Oct 28, 2014•48 min•Ep. 4
As CEO of a young startup, you can often feel what you are facing right now can make or break your company, can make or break you. And you will likely find yourself in this place more than once. Nigel Sharp, CEO of Armenian based Lion Sharp, finds himself in one of these very moments. He feels the energy of a promising product, and the reality of 6 months of runway. How do you balance the excitement and challenges? How do discuss the reality of your finances with your team? How do you discuss yo...
Oct 16, 2014•41 min•Ep. 3
