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 Ian join Jerry in today’s podcast to talk about their friendship, the importance of peer relationships in entrepreneurship, the relief of being heard by those who can empathize with your experience, as well as those who can challenge you from a place of love and deep understanding. Enjoy this discussion with Jerry, Ian Hogarth, and Yancey Strickler.
This conversation was recorded in early December, and since then Ian has announced his intention to give up the Co-CEO role at Soundkick and focus on his role at Chairman.
Reboot Podcast #31 - Why Being Real Matters- with Evgeny Shadchnevrebootio
So many entrepreneurs seek to model their leadership after the high-profile, successful giants of business. Should I be 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 questions. The real question is, “Who the fuck are you?” You’re not Steve Jobs. You’re not Jeff Bezos. You’re you. What does the leader within you look like?
In today’s conversation, Jerry is joined by Evgeny, Co-founder and CEO of Makers Academy. Ev wrestles with the question of whether it’s possible to scale an organization built around trust, or does success require a leader who governs by fear? Together they discover a more beautiful, more fundamental question --“Who is Evgeny?” In that answer they may find a path to personal alignment and more effective leadership.
Reboot Podcast #29 - Who's in Your Corner? - with Carrie Barryrebootio
Carrie Barry has had her own 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 former Olympic Boxer and entrepreneur who owns and runs a boxing gym in Boulder where people come to break a sweat, get a hug, and learn some valuable life lessons. She also happens to be, in a twist, a boxing coach for 2 of Reboot’s finest: Jerry and Ali. Join Jerry in getting a little coaching, and a lot of inspiration in this conversation with Carrie Barry.
Reboot Podcast #32 - Invest in Being Yourself - with Bryce Roberts and Chris ...rebootio
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 challenges. This conversation may leave you asking yourself:
In my own work, what are my values? What are my priorities? What am I wearing today?
Reboot Podcast #34 - Self actualization - with Henry May on Reboot Podcastrebootio
“Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakens.” – Carl Jung.
"Work is difficulty and drama, a high-stakes game in which our identity, our self-esteem, and our ability to provide are mixed inside us in a volatile, sometimes explosive ways.” from David Whyte in his incredible book, Crossing the Unknown Sea: Work as a pilgrimage of Identity.
That volatile, explosive mix is a gift. It presents a tremendous opportunity for us to do our own work, our inner work, and further develop our own understanding of self. In our conversation today, Jerry is joined by Henry May, founder and CEO of CoSchool, based in Columbia. Henry comes to Jerry with this very issue: How might the journey of entrepreneurship, specifically his own, open up new opportunities for him to grow? Or said more directly: How might he use his work at Coschool to do the real work on his humanity?
Reboot Podcast #28 - Reclaiming the Shadow - with Tracy Lawrence on Reboot Po...rebootio
Tracy Lawrence, Co-founder and CEO of Chewse, and Jerry Colonna talk about authenticity, leading from the heart and on the power of embracing the lost and disowned parts of ourselves. For Tracy, it’s not only about being there for the little girl who was bullied in middle school, but also about owning her very own inner bully. Reclaiming that part of herself will not only impact her approach to the latest company experiment, but it also might affect her own leadership and bring her and her company deeper into alignment.
Reboot Podcast #33 - Do I Even Have A Superpower?- with Kent Cavender-Baresrebootio
Have you ever asked yourself the question: I wonder if we'd be better off with someone else in my role?
In this podcast, a listener, Kent Cavender-Bares from Rowbots comes to Jerry with a question a similar question about his superpower: "What if my deep integrity, my commitment to simply telling how it is, is the reason we’re unable to fundraise? Do I even have a Superpower? Wouldn’t Rowbots, be further along if someone else was leading?" Jerry and Kent explore the double edge of a superpower, and how the path through his challenges may lie in a new set of questions: How can I be even more like Kent? How can I embrace my superpower? How can I believe in myself? And why is that so damned important?
Reboot Podcast #25 - Live Beyond Compare - Brad Feld and Jerry Colonna - Rebo...rebootio
It’s so easy, sometimes fun, sometimes painful, and always tempting to compare ourselves to others. As entrepreneurs, the temptation is even stronger. It can at times seem like there’s an endless supply of compare yourself material - from the media, to social media. Ask any Reboot coach...one of the busiest days as a coach is the day a big acquisition or funding announcement occurs. The second busiest is the day after. So what would it be like to let go? What if you stopped trying to be a VC / entrepreneur / father like everyone else? What if you were just you and that was OK?
That is exactly the advice our podcast guest offered up to a 34 year old Jerry Colonna - many, many years ago. We’re truly honored to have Brad Feld on the podcast with Jerry today. Brad 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 these two friends 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.
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot...rebootio
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 your superpower hiding in plain sight.
Reboot Podcast #31 - Why Being Real Matters- with Evgeny Shadchnevrebootio
So many entrepreneurs seek to model their leadership after the high-profile, successful giants of business. Should I be 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 questions. The real question is, “Who the fuck are you?” You’re not Steve Jobs. You’re not Jeff Bezos. You’re you. What does the leader within you look like?
In today’s conversation, Jerry is joined by Evgeny, Co-founder and CEO of Makers Academy. Ev wrestles with the question of whether it’s possible to scale an organization built around trust, or does success require a leader who governs by fear? Together they discover a more beautiful, more fundamental question --“Who is Evgeny?” In that answer they may find a path to personal alignment and more effective leadership.
Reboot Podcast #29 - Who's in Your Corner? - with Carrie Barryrebootio
Carrie Barry has had her own 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 former Olympic Boxer and entrepreneur who owns and runs a boxing gym in Boulder where people come to break a sweat, get a hug, and learn some valuable life lessons. She also happens to be, in a twist, a boxing coach for 2 of Reboot’s finest: Jerry and Ali. Join Jerry in getting a little coaching, and a lot of inspiration in this conversation with Carrie Barry.
Reboot Podcast #32 - Invest in Being Yourself - with Bryce Roberts and Chris ...rebootio
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 challenges. This conversation may leave you asking yourself:
In my own work, what are my values? What are my priorities? What am I wearing today?
Reboot Podcast #34 - Self actualization - with Henry May on Reboot Podcastrebootio
“Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakens.” – Carl Jung.
"Work is difficulty and drama, a high-stakes game in which our identity, our self-esteem, and our ability to provide are mixed inside us in a volatile, sometimes explosive ways.” from David Whyte in his incredible book, Crossing the Unknown Sea: Work as a pilgrimage of Identity.
That volatile, explosive mix is a gift. It presents a tremendous opportunity for us to do our own work, our inner work, and further develop our own understanding of self. In our conversation today, Jerry is joined by Henry May, founder and CEO of CoSchool, based in Columbia. Henry comes to Jerry with this very issue: How might the journey of entrepreneurship, specifically his own, open up new opportunities for him to grow? Or said more directly: How might he use his work at Coschool to do the real work on his humanity?
Reboot Podcast #28 - Reclaiming the Shadow - with Tracy Lawrence on Reboot Po...rebootio
Tracy Lawrence, Co-founder and CEO of Chewse, and Jerry Colonna talk about authenticity, leading from the heart and on the power of embracing the lost and disowned parts of ourselves. For Tracy, it’s not only about being there for the little girl who was bullied in middle school, but also about owning her very own inner bully. Reclaiming that part of herself will not only impact her approach to the latest company experiment, but it also might affect her own leadership and bring her and her company deeper into alignment.
Reboot Podcast #33 - Do I Even Have A Superpower?- with Kent Cavender-Baresrebootio
Have you ever asked yourself the question: I wonder if we'd be better off with someone else in my role?
In this podcast, a listener, Kent Cavender-Bares from Rowbots comes to Jerry with a question a similar question about his superpower: "What if my deep integrity, my commitment to simply telling how it is, is the reason we’re unable to fundraise? Do I even have a Superpower? Wouldn’t Rowbots, be further along if someone else was leading?" Jerry and Kent explore the double edge of a superpower, and how the path through his challenges may lie in a new set of questions: How can I be even more like Kent? How can I embrace my superpower? How can I believe in myself? And why is that so damned important?
Reboot Podcast #25 - Live Beyond Compare - Brad Feld and Jerry Colonna - Rebo...rebootio
It’s so easy, sometimes fun, sometimes painful, and always tempting to compare ourselves to others. As entrepreneurs, the temptation is even stronger. It can at times seem like there’s an endless supply of compare yourself material - from the media, to social media. Ask any Reboot coach...one of the busiest days as a coach is the day a big acquisition or funding announcement occurs. The second busiest is the day after. So what would it be like to let go? What if you stopped trying to be a VC / entrepreneur / father like everyone else? What if you were just you and that was OK?
That is exactly the advice our podcast guest offered up to a 34 year old Jerry Colonna - many, many years ago. We’re truly honored to have Brad Feld on the podcast with Jerry today. Brad 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 these two friends 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.
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot...rebootio
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 your superpower hiding in plain sight.
Reboot Podcast #22 - Does Anyone Know what they are Doing? With Sharon Salzbe...rebootio
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 our key teachers at Reboot, Sharon Salzberg, to the podcast. In this conversation, Sharon and Jerry discuss Sharon’s own entrepreneurial path, a new definition of success (and failure), authenticity, loving kindness and the question: Does anyone really know what they are doing?
Reboot Podcast #26 - Finding your Business Soulmate - Founders of The Grommet...rebootio
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 show) and her partner Joanne Domeniconi oni are the Co-founders of The Grommet. They join Jerry to talk about the beginning of their partnership, where and how they found alignment at the human level, how it has evolved over time, and the challenges it represents as they scale the business
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 wounds).
Reboot Podcast #20 with Bijan Sabet - Investors are Human toorebootio
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 and they explore some of the tensions that often arise between investors and entrepreneurs, the emotional perspective of the investor, and the importance of purpose and artistry. As a bonus, it includes Jerry reading a blessing at the end.
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
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 positive change in their lives. Ben comes to Jerry wondering how he can better deal with the negative inner dialogue. They quickly discover that inner voice, and more specifically the feelings that precede it, are a powerful indicator of an underlying fear. What opportunities exist in exploring that fear?
Reboot Podcast #11 - Stop and See: Mind Hacking, Meditation and Leadership - ...rebootio
“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 Wired’s "Smart List 2012: 50 people who will change the world."
In this episode, Vincent and Jerry talk about their mindfulness practices, how Vincent navigated his own ups and downs as an entrepreneur, and how meditation and mindfulness can create better leaders, and better organizations.
And be sure to listen all the way through the end, as Vincent has included a 10 minute guided meditation for you to kickstart your own mindfulness practice.
Reboot Podcast #36 - The Quest - with Jim Marsden and Jade Sherer on Reboot P...rebootio
Time and time again, I get the pleasure of seeing skeptical, but open Reboot Bootcampers enter the Colorado wilderness with instructions from Jim looking for a conversation – and time and time again I see them come back in shock with how the land opened new insights up for them. Jerry included.
In today’s special episode, Jerry Colonna, Jim Marsden and Jade Sherer talk about the power and opportunity of time on the land, how Jerry’s own experience on a vision quest, which was guided by Jim and Jade, and why a quest could change your own awareness forever. If it terrifies you, you are ready…
Reboot Podcast #9 - Investing in Trust - with Fred Wilson and Jerry Colonnarebootio
Fred Wilson barely needs an introduction for his role and impact in the startup community both as blogger and co-founder of Union Square Ventures. Fred’s also a big reason why I’m here giving this intro: his blog ultimately led me to meeting and now working with Jerry; and his family podcast, Positively 10th Street, was one of the first podcasts I ever listened to. Feels like things have come full circle.
So I’m thrilled to have Fred join Jerry for this episode. In 19 years of friendship and partnership in the startup world, these two have seen just about everything. In this conversation they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey. There’s a lot of great material referenced in this discussion, so we’ve gone ahead and compiled a bunch of links from this show on our podcast page at reboot.io/podcast.
In what we hope will be a series of several, enjoy this first Reboot conversation with Fred Wilson and Jerry Colonna.
Reboot Podcast #19 Building a House of Belonging with Tanisha Robinsonrebootio
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 generate more than $20M in revenue this year. But the company isn’t just about shirts and home goods, it’s a place where people (including a black, gay, woman from a Mormon family of 7 in a small town in Missouri) have a place to self-identify and a place to belong. As Tanisha shares, running a company fueled by your passion to make the world better is both exhilarating and heartwrenching.
Ben Saunders knows very well the ups and downs that come with attempting to do something extraordinary. 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’ a polar explorer. Between October 2013 and February 2014, he and his companion Tarka broke the record for the longest ever polar journey on foot. On their path to the South Pole, they faced temps of -50F and wind chills near -70F all while they covered nearly seventy marathons back-to-back on less than four hours of sleep a night.
This record breaking journey was nearly ten years in the making for Ben, and truly was an amazing accomplishment, but despite all that he found the inner journey that followed even more challenging than what he faced out on the ice. In this conversation, Ben and Jerry discuss his journey on and off the ice.
Reboot Podcast #8 - How Introspection Changed My Business - With Blaine Vess ...rebootio
“Knowing yourself is the beginning of all wisdom.”
― Aristotle
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 to help push his company to the next level. To achieve that, he didn’t look elsewhere, he looked within.
In this conversation, Jerry and Blaine talk about Blaine’s “year of introspection”. It included a stop at one of our bootcamps, working with a coach and a therapist, and that year ultimately helped him understand how and why he was holding himself back. Perhaps Blaine and Jerry’s conversation, our first of 2015, may spark your own year of introspection.
Reboot Podcast #39 - New Choices with Mary Lemmer on Reboot Podcastrebootio
Mary Lemmer came on to share her emotional story of seemingly everything working against her; her body giving in, her relationship ending, her business coming apart, losing her dad's approval, all in a very short period of time. Physically and emotionally, these were painful experiences for Mary and yet, what if they were exactly what she needs? What if this is the moment she was waiting for?
Reboot Podcast #37 - Are you a Servant Leader - with Patrick Campbell on Rebo...rebootio
For leaders the temptation to tell, fix, and even do is so strong. “I know the way,” or “I have the answers,” or “the buck stops with me.” Sometimes it’s impossible to resist the ego boost of providing the answer, giving the fix, telling the way. But what impact does this have on the team, and ourselves? And is it even true?
Jerry Colonna is joined today by Patrick Campbell, co-founder and CEO of Price Intelligently – a bootstrapped company in Boston. Patrick and Jerry explore different leadership styles, the power of “if I die docs,” and how the secret to leadership, and servant leadership, may not lie in having the right answers, but instead asking the right questions.
Reboot Podcast #05 - How Do You Define Success? With Jerry Colonna and Joseph...rebootio
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. Why is the drive, the itch to not sit still, so strong? What’s he running towards? Or perhaps running from?
Joseph and Jerry explore why he feels compelled to run, take a look at how & what Joseph is using to define success and why mindfulness is about so much more than meditation...it’s about expanding the space between stimulus and response.
Reboot Podcast #23 - With a Little More Care… with Sherman Lee and Jerry Colonnarebootio
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 staring down a draining bank account, a shaky business model, and a crippling fear: if I fail, I won’t be able to provide. A year later we sit with our 23rd podcast episode, a return visit from Sherman one of our first guests, and an opportunity to appreciate Sherman’s journey and growth since we last spoke.
Reboot Podcast #06 - Do you avoid difficult conversations? – with Jerry Colon...rebootio
“If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.”
Jesus, Gospel of Thomas
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 what it means to be fierce, and what’s behind the desire to make people happy. It’s a conversation that will leave you asking: “What if I led from place knew where i knew I was good and also know there are things I want to do better?”
Enjoy the conversation...
Q’s
What if you led from a place in which you knew you were good and knew the things you wanted to do better?
Reboot Podcast #7 - The Relationship between Depression and Entrepreneurship?...rebootio
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 alone. In this podcast, which is slightly different than past episodes, Jerry converses with Rand about his experience - his “loop,” how shame and guilt are at times his driver, the importance of understanding one’s emotional state, and how he’s made progress in coming out of his own depression, including his one piece of advice for entrepreneurs or anyone dealing with their own depression.
Reboot Podcast #45 – What’s Love Got to Do with It?- with Fred Wilson and Bra...rebootio
How can you expect to serve others, whether it be customers, portfolio companies, or your organization if your own house is not in order? We are so fortunate to 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 is truly incredible.
Reboot Podcast #38 - Plant seeds of your life - With Congressman Tim Ryan on ...rebootio
Congressman Tim Ryan is our guest for Episode 38 of the Reboot Podcast. Tim is a special guy, and not just because he’s a congressman, and not just because he’s from Ohio – though that’s pretty great too – but because he’s committed to bringing heart, humanity, mindfulness and a long-term focus into a space that doesn’t always welcome it: government. In this conversation (originally recorded in November), Tim shares his journey to mindfulness, his ongoing practice in noticing his own inner conversation, and his commitment to mindfully planting seeds for the future and having the patience to watching them grow.
Reboot Podcast #15 - Becoming a Leader: The Crucible of Co-Founder Conflict w...rebootio
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 largest video platforms, we have the 3 co-founders of JW Player joining Jerry in person. In a very open conversation, they explore key challenging moments in their company and partnership history -and how they emerged from those moments stronger and more committed than ever. It's an inspiring story of leaders born through adversity
Reboot Podcast #04 - The hidden burdens in our work – with Jerry Colonna, She...rebootio
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, fears that entrepreneurs will know all too well.
Reboot Podcast #22 - Does Anyone Know what they are Doing? With Sharon Salzbe...rebootio
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 our key teachers at Reboot, Sharon Salzberg, to the podcast. In this conversation, Sharon and Jerry discuss Sharon’s own entrepreneurial path, a new definition of success (and failure), authenticity, loving kindness and the question: Does anyone really know what they are doing?
Reboot Podcast #26 - Finding your Business Soulmate - Founders of The Grommet...rebootio
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 show) and her partner Joanne Domeniconi oni are the Co-founders of The Grommet. They join Jerry to talk about the beginning of their partnership, where and how they found alignment at the human level, how it has evolved over time, and the challenges it represents as they scale the business
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 wounds).
Reboot Podcast #20 with Bijan Sabet - Investors are Human toorebootio
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 and they explore some of the tensions that often arise between investors and entrepreneurs, the emotional perspective of the investor, and the importance of purpose and artistry. As a bonus, it includes Jerry reading a blessing at the end.
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
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 positive change in their lives. Ben comes to Jerry wondering how he can better deal with the negative inner dialogue. They quickly discover that inner voice, and more specifically the feelings that precede it, are a powerful indicator of an underlying fear. What opportunities exist in exploring that fear?
Reboot Podcast #11 - Stop and See: Mind Hacking, Meditation and Leadership - ...rebootio
“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 Wired’s "Smart List 2012: 50 people who will change the world."
In this episode, Vincent and Jerry talk about their mindfulness practices, how Vincent navigated his own ups and downs as an entrepreneur, and how meditation and mindfulness can create better leaders, and better organizations.
And be sure to listen all the way through the end, as Vincent has included a 10 minute guided meditation for you to kickstart your own mindfulness practice.
Reboot Podcast #36 - The Quest - with Jim Marsden and Jade Sherer on Reboot P...rebootio
Time and time again, I get the pleasure of seeing skeptical, but open Reboot Bootcampers enter the Colorado wilderness with instructions from Jim looking for a conversation – and time and time again I see them come back in shock with how the land opened new insights up for them. Jerry included.
In today’s special episode, Jerry Colonna, Jim Marsden and Jade Sherer talk about the power and opportunity of time on the land, how Jerry’s own experience on a vision quest, which was guided by Jim and Jade, and why a quest could change your own awareness forever. If it terrifies you, you are ready…
Reboot Podcast #9 - Investing in Trust - with Fred Wilson and Jerry Colonnarebootio
Fred Wilson barely needs an introduction for his role and impact in the startup community both as blogger and co-founder of Union Square Ventures. Fred’s also a big reason why I’m here giving this intro: his blog ultimately led me to meeting and now working with Jerry; and his family podcast, Positively 10th Street, was one of the first podcasts I ever listened to. Feels like things have come full circle.
So I’m thrilled to have Fred join Jerry for this episode. In 19 years of friendship and partnership in the startup world, these two have seen just about everything. In this conversation they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey. There’s a lot of great material referenced in this discussion, so we’ve gone ahead and compiled a bunch of links from this show on our podcast page at reboot.io/podcast.
In what we hope will be a series of several, enjoy this first Reboot conversation with Fred Wilson and Jerry Colonna.
Reboot Podcast #19 Building a House of Belonging with Tanisha Robinsonrebootio
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 generate more than $20M in revenue this year. But the company isn’t just about shirts and home goods, it’s a place where people (including a black, gay, woman from a Mormon family of 7 in a small town in Missouri) have a place to self-identify and a place to belong. As Tanisha shares, running a company fueled by your passion to make the world better is both exhilarating and heartwrenching.
Ben Saunders knows very well the ups and downs that come with attempting to do something extraordinary. 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’ a polar explorer. Between October 2013 and February 2014, he and his companion Tarka broke the record for the longest ever polar journey on foot. On their path to the South Pole, they faced temps of -50F and wind chills near -70F all while they covered nearly seventy marathons back-to-back on less than four hours of sleep a night.
This record breaking journey was nearly ten years in the making for Ben, and truly was an amazing accomplishment, but despite all that he found the inner journey that followed even more challenging than what he faced out on the ice. In this conversation, Ben and Jerry discuss his journey on and off the ice.
Reboot Podcast #8 - How Introspection Changed My Business - With Blaine Vess ...rebootio
“Knowing yourself is the beginning of all wisdom.”
― Aristotle
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 to help push his company to the next level. To achieve that, he didn’t look elsewhere, he looked within.
In this conversation, Jerry and Blaine talk about Blaine’s “year of introspection”. It included a stop at one of our bootcamps, working with a coach and a therapist, and that year ultimately helped him understand how and why he was holding himself back. Perhaps Blaine and Jerry’s conversation, our first of 2015, may spark your own year of introspection.
Reboot Podcast #39 - New Choices with Mary Lemmer on Reboot Podcastrebootio
Mary Lemmer came on to share her emotional story of seemingly everything working against her; her body giving in, her relationship ending, her business coming apart, losing her dad's approval, all in a very short period of time. Physically and emotionally, these were painful experiences for Mary and yet, what if they were exactly what she needs? What if this is the moment she was waiting for?
Reboot Podcast #37 - Are you a Servant Leader - with Patrick Campbell on Rebo...rebootio
For leaders the temptation to tell, fix, and even do is so strong. “I know the way,” or “I have the answers,” or “the buck stops with me.” Sometimes it’s impossible to resist the ego boost of providing the answer, giving the fix, telling the way. But what impact does this have on the team, and ourselves? And is it even true?
Jerry Colonna is joined today by Patrick Campbell, co-founder and CEO of Price Intelligently – a bootstrapped company in Boston. Patrick and Jerry explore different leadership styles, the power of “if I die docs,” and how the secret to leadership, and servant leadership, may not lie in having the right answers, but instead asking the right questions.
Reboot Podcast #05 - How Do You Define Success? With Jerry Colonna and Joseph...rebootio
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. Why is the drive, the itch to not sit still, so strong? What’s he running towards? Or perhaps running from?
Joseph and Jerry explore why he feels compelled to run, take a look at how & what Joseph is using to define success and why mindfulness is about so much more than meditation...it’s about expanding the space between stimulus and response.
Reboot Podcast #23 - With a Little More Care… with Sherman Lee and Jerry Colonnarebootio
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 staring down a draining bank account, a shaky business model, and a crippling fear: if I fail, I won’t be able to provide. A year later we sit with our 23rd podcast episode, a return visit from Sherman one of our first guests, and an opportunity to appreciate Sherman’s journey and growth since we last spoke.
Reboot Podcast #06 - Do you avoid difficult conversations? – with Jerry Colon...rebootio
“If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.”
Jesus, Gospel of Thomas
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 what it means to be fierce, and what’s behind the desire to make people happy. It’s a conversation that will leave you asking: “What if I led from place knew where i knew I was good and also know there are things I want to do better?”
Enjoy the conversation...
Q’s
What if you led from a place in which you knew you were good and knew the things you wanted to do better?
Reboot Podcast #7 - The Relationship between Depression and Entrepreneurship?...rebootio
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 alone. In this podcast, which is slightly different than past episodes, Jerry converses with Rand about his experience - his “loop,” how shame and guilt are at times his driver, the importance of understanding one’s emotional state, and how he’s made progress in coming out of his own depression, including his one piece of advice for entrepreneurs or anyone dealing with their own depression.
Reboot Podcast #45 – What’s Love Got to Do with It?- with Fred Wilson and Bra...rebootio
How can you expect to serve others, whether it be customers, portfolio companies, or your organization if your own house is not in order? We are so fortunate to 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 is truly incredible.
Reboot Podcast #38 - Plant seeds of your life - With Congressman Tim Ryan on ...rebootio
Congressman Tim Ryan is our guest for Episode 38 of the Reboot Podcast. Tim is a special guy, and not just because he’s a congressman, and not just because he’s from Ohio – though that’s pretty great too – but because he’s committed to bringing heart, humanity, mindfulness and a long-term focus into a space that doesn’t always welcome it: government. In this conversation (originally recorded in November), Tim shares his journey to mindfulness, his ongoing practice in noticing his own inner conversation, and his commitment to mindfully planting seeds for the future and having the patience to watching them grow.
Reboot Podcast #15 - Becoming a Leader: The Crucible of Co-Founder Conflict w...rebootio
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 largest video platforms, we have the 3 co-founders of JW Player joining Jerry in person. In a very open conversation, they explore key challenging moments in their company and partnership history -and how they emerged from those moments stronger and more committed than ever. It's an inspiring story of leaders born through adversity
Reboot Podcast #04 - The hidden burdens in our work – with Jerry Colonna, She...rebootio
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, fears that entrepreneurs will know all too well.
Zelle Nelson and Maureen McCarthy are not only co-founders of The Center For Collaborative Awareness, but they are also married to each other. They created a collaboration process called “The Blueprint of We” in 1998 as they began their dating relationship. This collaboration process is used to build and sustain healthier, more resilient business and personal relationships, which makes day-to-day interactions effortless and time together creative and productive. This process is facilitated through completing a document that has five components: The Story of Us, Interaction Styles and Warning Signs, Expectations, Questions to Return to Peace, and Short and Long-Term Agreements. Maureen and Zelle are using the Blueprint of We process and document to create a place where people actually look forward to going to work where everyone’s knowledge, passions, and interests rise to the surface to create a stronger and more vibrant company or community.
Reboot Podcast #44 – We are Designed to Fail – with Nicholas Russell and Jerr...rebootio
Startups fail, we hear that all the time. Failure is good, we hear that all the time too. But we rarely hear about the pain, the shame and the second-guessing that comes with it. Even worse, at least for me, we rarely hear about the opportunities that lie, or may lie in something ending beyond just a pivot or a lesson learnt. In that moment, reading that email on the bench, my feet hurting, I wished someone would have told me what I know now to be true. This startup failing is not proof that something is broken within you. In fact, it's an opening and an opportunity to find something new within you and for you.
Reboot Podcast #41 - Being a superhero with John Guydon on Reboot Podcastrebootio
Our deepest fear is that we are powerful beyond measure. How does that land for you? For me, I got to be honest, it feels like it was written for somebody else, a different type of person, a more capable and more talented and more powerful type of person. But it wasn’t. It's a reminder to us all that within us, we have the capacity to, as our guest says today, make really heavy, seemingly immovable things, move. In other words, we have great power if we choose to own it. The choice is always there and ours to make
Reboot Podcast #10 - Fail with Honor - with Derek Bereit, Beth McKeon, & Jer...rebootio
“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 McKeon, Founder and CEO of Kids Calendar, who is dealing with another common challenge: How do you find, recruit and hire the right person for your startup at the stage that it’s in?
As always we’d love to hear feedback from you either on our website or on twitter @reboothq. Now on with to the conversations.
So Whats Your Story? Power Networking Tips & TecnhniquesRae Stonehouse
Rae Stonehouse, author of Power Networking for Shy People: Tips & Techniques for Moving from Shy to Sly! Offers proven sage advice on how to maximize your business networking effectiveness.
In So What’s Your Story? Rae provides sage advice on how to have a story ready at a moment’s notice to highlight you and your business.
Reboot Podcast #01 - How self reflection potentially saved a business - the r...rebootio
Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joins Jerry for this episode to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended a CEO bootcamp last October and begin to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge that could have destroyed his business. Derek’s openness and introspection is inspiring, and will inspire you to re-examine how your own stories impact your business and your life.
Reboot Podcast #43 – The Dharma of Inclusivity – with Konda Masonrebootio
There is real suffering out there and that suffering that is causing violence. What are some of the causes of the suffering and how might we address those?
It’s a true honor to welcome entrepreneur, creator, and teacher, Konda Mason to the podcast for an important and timely conversation with Jerry. This discussion was recorded last week, and we thought it was really important to get this out sooner rather than later, particularly given the events in Orlando. Konda and Jerry address some of the source causes of this suffering, this pain, and what opportunities might lie in remembering we’re all in this together. This conversation will challenge you on your own privileges and inspire you find new ways of connecting with people from all backgrounds.
Keep your thoughts healthy – with Eric Zimmer
It’s really easy to get stuck into a pattern of circling around the same negative thoughts over and over.
It’s also really easy to shut down any of your negative thoughts and say, “Everything’s great!”
In this episode, among other things, Eric and I cover how to keep your thoughts as healthy as possible without going to either extreme.
http://rachelrofe.com/keep-your-thoughts-healthy-with-eric-zimmer
Want More?
If you liked this, there’s plenty more where it come from. Let’s stay in touch!
We can connect in any of these places:
Main website: http://www.RachelRofe.com
A Better Life Podcast – where these transcripts are taken from:
http://www.rachelrofe.com/podcast
Rachel's books – Learn new ways to improve your life:
http://www.rachelrofe.com/booklist
Twitter: http://www.Twitter.com/RachelRofe
Twitter: http://www.Twitter.com/AbetterlifeRR
Instagram: http://www.Instagram.com/RachelRofe
Instagram: http://www.Instagram.com/chooseabette...
YouTube: http://www.YouTube.com/RachelRofe
YouTube: http://www.YouTube.com/Chooseabetterlife
Did you miss our last episode?
You can get it here: http://rachelrofe.com/how-to-be-charismatic-with-jordan-harbinger
Discover the innovative and creative projects that highlight my journey throu...dylandmeas
Discover the innovative and creative projects that highlight my journey through Full Sail University. Below, you’ll find a collection of my work showcasing my skills and expertise in digital marketing, event planning, and media production.
At Techbox Square, in Singapore, we're not just creative web designers and developers, we're the driving force behind your brand identity. Contact us today.
buy old yahoo accounts buy yahoo accountsSusan Laney
As a business owner, I understand the importance of having a strong online presence and leveraging various digital platforms to reach and engage with your target audience. One often overlooked yet highly valuable asset in this regard is the humble Yahoo account. While many may perceive Yahoo as a relic of the past, the truth is that these accounts still hold immense potential for businesses of all sizes.
Company Valuation webinar series - Tuesday, 4 June 2024FelixPerez547899
This session provided an update as to the latest valuation data in the UK and then delved into a discussion on the upcoming election and the impacts on valuation. We finished, as always with a Q&A
Premium MEAN Stack Development Solutions for Modern BusinessesSynapseIndia
Stay ahead of the curve with our premium MEAN Stack Development Solutions. Our expert developers utilize MongoDB, Express.js, AngularJS, and Node.js to create modern and responsive web applications. Trust us for cutting-edge solutions that drive your business growth and success.
Know more: https://www.synapseindia.com/technology/mean-stack-development-company.html
Building Your Employer Brand with Social MediaLuanWise
Presented at The Global HR Summit, 6th June 2024
In this keynote, Luan Wise will provide invaluable insights to elevate your employer brand on social media platforms including LinkedIn, Facebook, Instagram, X (formerly Twitter) and TikTok. You'll learn how compelling content can authentically showcase your company culture, values, and employee experiences to support your talent acquisition and retention objectives. Additionally, you'll understand the power of employee advocacy to amplify reach and engagement – helping to position your organization as an employer of choice in today's competitive talent landscape.
Anny Serafina Love - Letter of Recommendation by Kellen Harkins, MS.AnnySerafinaLove
This letter, written by Kellen Harkins, Course Director at Full Sail University, commends Anny Love's exemplary performance in the Video Sharing Platforms class. It highlights her dedication, willingness to challenge herself, and exceptional skills in production, editing, and marketing across various video platforms like YouTube, TikTok, and Instagram.
B2B payments are rapidly changing. Find out the 5 key questions you need to be asking yourself to be sure you are mastering B2B payments today. Learn more at www.BlueSnap.com.
The 10 Most Influential Leaders Guiding Corporate Evolution, 2024.pdfthesiliconleaders
In the recent edition, The 10 Most Influential Leaders Guiding Corporate Evolution, 2024, The Silicon Leaders magazine gladly features Dejan Štancer, President of the Global Chamber of Business Leaders (GCBL), along with other leaders.
Reboot Podcast #30 - Who Do You Turn To? - with Yancey Strickler and Ian Hogarth
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A Reboot peer group is a hand-selected group of entrepreneurs and leaders who meet in
supportive Reboot coach-facilitated sessions twice a month. So, what are these groups really
like? We asked a peer group member to share his experience.
“Hi, my name is Bobby Brannigan. I am co-founder and CEO at Mercato. One of the biggest
challenges that I face as an entrepreneur has been navigating the waters of solving hard problems
while under extreme stress. You can’t be open and honest with everyone about your business
because you don’t want to scare people away, you don’t want to get people nervous because that
is going to upset their ability to do what they have to do. At the same time, there are not a lot of
people that actually could relate to these situations so, having a group you can turn to is
extremely beneficial and it allows you not only to spend more time thinking about these issues
and how to better solve them, but hearing yourself explain them out loud and getting people to
question different routes that you might think about taking and that kind of stuff is invaluable.
It’s been great to have that group to really think in a much deeper sense with people that sharing
the same challenge and they really trying to grow and really get out of that comfort zone just as I
am. That’s been really excellent for me.”
So, who do you turn to? What if you had a community of peers who were committed to
supporting you, like Bobby, a group you knew you could always count on? There is great power
in knowing you are not alone. Learn more about Reboot’s peer groups at reboot.io/peers.
**
“As you point out, the CEO can say things to the coach that they can't say to almost anybody
else, but equally important is that relationship that one can have with someone who just gets it.
There is a similarity and a universality to the experience that only a peer really, truly grasps and
to be able to talk to somebody about that is, you know, incredibly helpful.”
Welcome to the Reboot podcast.
“Watch carefully, the magic that occurs when you give a person just enough comfort to be
themselves.” – Atticus.
In the fall of 2013, my startup was circling the drain. We’d made a bet to scrap just one revenue-
generating model in favor of a far riskier swing for the fences, and it was not working at all. The
team was barely speaking to each other and the weight as a co-founder was overwhelming.
Thankfully, I always had Tuesday evening. Tuesday night was my space and time to connect
with another entrepreneur, someone who really knew the ups and downs, the wins and losses, the
challenges of being an entrepreneur. Tuesday night was my space and time to be reminded the
weight was real that I wasn’t alone in shouldering it. That is what Tuesday evening was for me.
There’s a saying, “Behind every great man is a great woman” I would say that behind every great
entrepreneur, is a great friend, someone who not only accepts their wholeness, but demands it.
The entrepreneurial path simply can't be travelled alone. So when Jerry asked kick-starter CEO
and co-founder Yancey Strickler “Who do you turn to?” his response was immediate. “Ian
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Hogarth, co-founder and chairman of Songkick.” So, we are grateful and thrilled to have Yancey,
Ian and Jerry talk about the importance of peer relationships in entrepreneurship, the relief of
being heard by those who can truly empathize with your experience, as well with those who can
challenge you from a place of love and deep understanding. So, enjoy this conversation between
Jerry, Ian Hogarth and Yancey Strickler, about their own version of Tuesday evening.
This conversation was recorded in early December and since then, Ian has announced his
intention to give up the co-CEO role and focus more on his role as chairman at Songkick. I’d
encourage everyone to read his very well-written blog post on his transition, which you can find
along with quote and other key links on our website, at reboot.io/podcast.
**
Jerry Colonna: Hey guys, thanks for coming on this show; Ian, Yancey, it’s really, really
a pleasure to have you on the show today. Before we get started, why don’t you
both take a moment and just sort of introduce yourselves and this way people
could sort of associate voices with names and that sort of thing.
Yancey Strickler: Yeah, I’m Yancey, I’m CEO of Kickstarter.
Ian Hogarth: Hi, I am Ian; I am the co-CEO of Songkick.com.
Jerry: And tell us a little bit about Songkick.
Ian: Songkick is the largest concert discovery service in the world with about ten
millions fans using us every month; selling tickets for some of the world’s biggest
artists like Adele, Mumford & Sons and Kenny Chesney.
Jerry: So basically if I need tickets to a hot show, I can call you?
Ian: You can call me, yeah.
Jerry: I might not do anything, but –
Yancey: There’s multiple, interesting things in what Ian just said I just want to point out.
Number one, co-CEO, we’ll talk about that, Ian has multiple peers and another is
Adele. I haven’t had the chance to talk to Ian yet since this happened, but
Songkick, this week, sold the tickets for Adele’s new tour in a totally new way
that seems like it went incredibly well.
Ian: Yeah, I mean, it’s been a pretty intense week. As you guys both know, I mean,
Adele is the biggest artist in the world by quite a long way right now. She just
blew past recorded music tallies that were set 15 years ago, and she’s partnered
with us to sell tickets to her recently announced tour. And the tour is obviously
huge just because she is, you know, such a unique artist, but it’s particularly huge
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because she is the highest demand artist in the world who hasn’t toured for five
years. So, the number of people who want tickets to see her live is somewhere
between ten and a hundred times the number of available tickets, which typically
means they end up within about five seconds on the re-sale market being touted
by people for ten times the value. We launched some new stuff with her, which is
obviously quite an intense thing to do with the biggest tour of the year, but that
new stuff worked and we reduced the amount to some of the secondary markets
about [Inaudible 0:07:08] using proprietary new technology. So it’s been a super,
super intense week; very, very rewarding to see our new products working.
Yancey: That’s awesome. I’m happy for you.
Jerry: That’s amazing and I want to take note of the fact that Yancey brought us right
back to that with a certain amount of pride in you, friend. Isn’t that true, Yancey?
Yancey: Well, yeah, definitely. I mean, it’s funny, Ian and I talk a lot about what we do,
but Ian is like just a proper person and does things the right way and so he told me
about what they were doing but he didn’t tell me who it was with. He just said “a
major artist” and then when I saw the Adele thing this week, I was like, “Oh that’s
who it was.” But he, you know, even at a one-on-one dinner, late, he keeps it
clean. So I was just excited to see that news this week. And also, it’s funny, I
mean, even – it’s just funny, the emotions that come with watching other people
succeed, I mean, I think that often even if it’s unrelated to you, there could be
feelings of jealousy with seeing other people do well, but with a friend like this, I
mean, when I saw that stuff happen, I was just over the moon about it. So, you
know, it’s good to give a shout out when you know, when you really can with a
clear heart and you know, you really do just feel really excited by something that
someone has done.
Jerry: I think that’s beautifully said Yancey and part of the reason why I was so
interested in having the two of you come on this show was to talk about the
experience of being friends with another CEO and the ways in which we can all
gain support just by talking to peers and just by having a conversation. And I
think, you just sort of dove right into it, which is this notion of how does one feel
about a friend’s success, because it can involve all sorts of feelings there.
Ian: I think that one of the more interesting things about is that you, you know,
Yancey and I don’t – most of the time we don’t really – you know, we are trying
to solve problems that face our business and sort of share challenges we are facing
and so, you know, typically all the really good stuff that is going on, we find out
about through the press.
Yancey: It’s totally true.
Ian: All the challenging stuff is like the stuff we talk about and so I think the facts that
you know the other stuff that’s going on with someone’s company at any given
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point in time is also like a really unique amount of context to have when you are
seeing all the stuff play out in public. I mean, I think it’s interesting though you
know, although I had to be, you know, kind of very discrete about who it was that
I was working with just because I mean, it’s really such an enormous artist, I
think, in general, I was thinking about this, you know, what we are going to talk
about on this call today, and I think the biggest thing for me is like as a CEO, you
sort of have to have all these things in your head that you can't really talk to
anyone else about, and so what’s unique about having a relationship where you
really trust someone who understands the challenges, the role, but who you can
also trust with highly sensitive information, is you can kind of like, unburden
yourself I suppose of some of the – not exactly the weight, but the fact that things
are just ricocheting around in your own head and you haven’t got an outlet for it.
And obviously you can do a lot with co-founders and board members, but I think
there’s a unique – as you know Jerry, as being a coach, you know that a coach is
here and he has a different set of things to than what a board member can
typically hear. And I think up here is an even more unique relationship if you
have the trust there because you can share stuff not just as a – you can share stuff
where you suspect there is a [Inaudible 0:11:20] of experience going on that you
can draw from as well as maybe a more experienced, veteran’s kind of experience
that you can draw from like a coach.
Jerry: Yeah. I think, again, I think you said it incredibly well. You know, one of the
things that – the coach relationship can be very, very helpful because as you point
out, the CEO can say things to the coach that they can't say to almost anybody
else, but equally important is the relationship that one can have with someone
who just gets it because even if their company is, you know, completely different
market, or even as in the case of the two of you, you are in completely different
countries, there is a similarity and a universality to the experience that only a peer
really truly grasps. And to be able to talk to somebody about that is, you know,
incredibly helpful. Tell me, what is it that – so you mentioned that you tend to
turn to each other, not so much to share the good news, but to just share the
experiences, the other experiences; what sort of things have you talked through
without going into any details that might be revealing otherwise?
Yancey: I mean, I think that we talk about probably looming decisions that maybe we feel
nervous about, you know, you are just kind of running it through with someone,
and you know, just like there is a set of emotions and various tensions that come
with like making a big decision and enacting a big decision that you know, I just –
I know that Ian implicitly understands. Like, there is no need to explain and like
once this happens then all these other things like, I think we both understand what
it is to make a decision in a job like this. I think it’s a lot of that and then yeah,
just probably processing, you know, I mean, sometimes these conversations are,
yeah, not dissimilar to a coach relationship, but I think a little more intimate
where you just want to say something out loud and try to understand what it is
that you really think about something you know, through talking about it with
someone else. I agree with Ian that it is about challenges; there is that – Ian
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brought this up the last time we were hanging about a month ago in London, a
New Yorker profile of Reid Hoffman talks about how he has meals – it’s him and
Mark Pincus having dinner together and each bring their list of things they want
to talk about. But their list is like, I don’t know, lobbying the president for
something, so maybe that is what it is like on the other side, you know, once you
are out, you know, once you have made it, that’s what it is [Crosstalk] for now
it’s just challenge.
Ian: I mean, just to riff on that, my main point was that we should satirize with the
contents of the rest of our dinner by being like, “I’m stacking on Ai, what are you
stacking on?” That is just so transactional but –
Yancey: Just a couple of weeks ago, I had breakfast with another peer CEO, someone that
Ian and I are both friends with, and yeah, it was the same kind of deal, we saw
each other, great to see each other, he was reading like a highly intellectual book
that I immediately bought and was fantastic, and we sort of caught up but then
immediately it was like, “So you know, what is bringing you pain right now?”
And we just did that for an hour-and-a-half and talked it through and each of us,
we just like went back and forth. Yeah, it’s amazing, at the end of the day you feel
so light and you are like, all right, so my problems are not as bad as I thought
because like you are someone that I think of as being hyper-successful and their
problems are actually quite similar and you know, and then like, it’s always easier
to tell someone else what to do than it is to do something on your own. And so it
just brings clarity and confidence.
Ian: Right; I mean, on that note, one thing I was thinking about, you know, on this
broad topic was I had a walk one time with Yancey in London, where I’d really
been agonizing over a member of my exact team who had been underperforming
for a while, and I was essentially – I had basically made the decision to sort of let
them go, but Yancey just said, “Yeah, you should do that.” And it’s that external
perspective that you know, someone knows you well enough to not beat about the
bush, but also you know, has the distance to sort of help you, you know, kind of
validate something that you can't really talk about with the other members of your
team. I think outside of the wrestling with the generic problem set you face as a
founder or CEO, I think the other thing that is sort of unique about what Yancey
and I have is that we are both really, I guess, intellectually and emotionally
curious about the intersection of art and culture and our businesses are trying to
make a contribution at that intersection and have been for some time now, and
both of us have been doing this for close to ten years. And so we are both really,
really interested in where – what is that a creator wants from the internet, what is
that the consumer wants from me, where are the tensions there, what are the
opportunities, what have you seen as really cool and a lot of – there’s a sort of set
of things that I guess we typically talk about which is just, should I – what do you
think about this issue of my management team or I’ve got this deal I’m looking at,
do you think it makes sense, or board conversations, or whatever those kinds of
things, but the other half of what we talk about is like, I’ve got this kind of crazy
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idea about what I think is going to happen next, like, I don’t know if this is going
to work, I don’t know if this is a really good idea, what do you think about it and
this feeling around the edges of the avant guard ideas in our marketplace broadly
where art meets tech and that is really unique to have someone to share that with
because I think it’s sort of – it’s rare you meet people as interested in both of
those areas and kind of working at the cutting edge of it.
Yancey: Totally, and I think also, I mean, how Ian and I met, you know, there is this music
conference in Cannes called Midem that we both went to, five or six years ago,
and there was a guy named Ian Rogers who was the head of Apple Music and
CEO of Beats Music and now has gone to Louis Vuitton because – but just a great
guy and someone like, he liked both of us and so he brought us together into this
into this house with a couple of other guys, you know, Anthony Volodkin from
Hype Machine, James [Inaudible 0:18:57] from 61 and a few other people, but
like all kind of like-minded people of like techie-art people who just like are super
fans and are really committed to a certain set of ideals, and I still feel like that
cohort group that I am a part of and probably some of the people that I most love
and respect in this universe, like I just feel such a kinship with them and it was
just – you know, for Ian and I, we just shared a room together at a conference for
four days, but it was – it just created a very lasting and meaningful friendship that
will take us long and beyond our current careers. It brought us together and had a
very similar kind of perspective and value set.
Jerry: I’m noting the importance of that sense of cohort, that sense of – even if the
businesses aren’t precisely the same, you are both launching SAS businesses or
something like that, there is a sense of shared view of the world and shared
experience that seems to have enhanced the relationship; am I seeing that
correctly?
Ian: Yeah, I think also just the – I think the number of people who are really obsessed
with this little – this one kind of area of kind of business, kind of creativity like
technology is actually quite small and I think that it’s kind of being – that
happened to be sort of a lucky meeting of lots of people, I mean, maybe not lucky
when you consider Ian kind of put us all in the house, but, I think it was the fact
that at that point in time, this – maybe the technology landscape was less, you
know, frantic and the people working in that area were maybe people who were a
little bit going against the grain of it, just because it was not necessarily an
obvious thing to build something like Songkick or like Kickstarter or Hype
Machine or 61 or the Top Spin which is Ian’s project, so I think that maybe the
cohort was almost the fact that we were like slightly out of the hype cycle. I mean,
I remember when I went to the house, I didn’t actually know what a lot of other
people – I had heard of other people’s companies, but didn’t necessarily like
unless you, you know, spend a ton of time playing with the products and it was
like a real chance to, you know, immerse myself in some other projects that were
at a relatively early stage that I was kind of privileged enough to get to know
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when they were being kind of in a really experimental phase before they had kind
of blown up.
Yancey: Do you have that with Y Combinator at all Ian? You were early YC, like are these
communities sort of things quite typical, like is ours more specific than as usual,
what is your sense of that?
Ian: I think with Y Combinator, so many of the startups stayed in California after we
finished the batch that there was kind of a really strong San Francisco based
offline network that made it a bit challenging to preserve the same kind of
closeness if you were based remotely. I mean, I see people like Drew Houston and
Daniel when I’m over in San Francisco, but it’s just a bit different because I think
they were all like in the same apartment block for two years afterwards, and that
just creates different kinds of connections. I think in a way, the other kind of the
friendship I have with Yancey is very unique one, but other close kind of
relationships I have in the startup world, I think there is one thing in common that
sort of has lead to them, which is you know, one party makes a decision to share
something that seriously stressed about gets help and then something is kind of
forged, a new kind of trust and it’s pretty hard to do because usually the thing is
barely massive. So you know, just thinking about a friend of mine in London you
know, he was about to go through like a really horrific experience with his
business and he just needed someone to talk it over and he called me. I didn’t
really know him that well, but he sort of unburdened himself and then you know,
when something was going on with me, I’d call him back and I think you know,
probably I’ve read some of your blog posts, Jerry, and I think it’s this – there’s a
kind of I suppose a southern moment of like nakedness I guess, where you are just
like sharing something really raw and really like sensitive and something that you
are just like scared to tell anyone else, but that is the thing that ultimately opens
up the ability to share those things going forward and then at some point it just
becomes like zero fear to share things you are pretty – things that have that same
quality. I mean, if like something crazy was going on with Songkick, I would just
call Yancey and I wouldn’t even really think about the fact that I was telling him
something whereas if it was any other person, I would feel a lot more vulnerable.
So, I think you never get a relationship like the one that Yancey and I have or that
Yancey have with other peers or I do without that first moment of extreme
vulnerability.
Jerry: Yeah, let me jump in and thank you for sharing that story because I think you –
with that observation, you really bring out a very important point which is that if
you are going to avail yourself of this kind of support, someone has to go first.
Someone has to be willing to open up and be real, be authentic, be vulnerable and
share what is really going on. What I often do with – at the start of the bootcamps
is, I lay out a notion which is, ‘The bull shit stops here.’ The whole, ‘We are
killing it’ notion, the way startup CEOs and founders will try to kind of do an
almost dance around each other and pretend everything is great, when of course it
is not. That doesn’t mean everything sucks, it just means it’s not as great as you
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would tell your investors this and by doing so, to your point, Ian, you make
yourself available for the kind of support that a really good friend and peer can
deliver.
Ian: I think the other thing I’d say on that topic is like, Paul Graham once said
something to me, where he said like, you know, if you are involved with enough
startups, you realize that every startup is fucked –
Jerry: Yes.
Ian: – and no startups are actually like as good as they look from the outside. I think
it’s easy to hear that, but it’s really, really hard to believe that when you are like
reading TechCrunch every day, and I remember like I had – one day where I had
a call with Yancey and I had a call with another friend of mine, and you know, I
think that Kickstarter is one of the most phenomenally disruptive, transformative,
awesome companies on the internet and you know, my other friend has a similar
business in that sense, both of them were just dealing with really bad days. You
know, there’s like tons of stuff that was hard to deal with and challenging and
really stressful and I remember thinking wow, like this is – I should really just
take Paul Graham’s statement as gospel now; like I’m probably not going to get
more evidence at this point, and it was very – it was kind of like a weird moment
when I just thought like how much of it is service we all do each other by not
being more real in public. You know, it’s somehow I don’t know, it’s like the
need to play a certain narrative for the press, as I think actually is pretty harmful
to most founders’ psychology.
Jerry: I think you said it really well. I think one of the most important things I try to do
is normalize the entire range of experiences and, you know, as I often say, just
because you feel like shit, doesn’t mean you are shit, and you know, that just
because your company is fucked up, doesn’t mean it’s more fucked up than the
company down the street, and it also doesn’t mean you are going to fail. It just
means that all companies start off in the sort of unhealthy, dysfunctional, crazy
state and the movement is towards a kind of more functional while still
maintaining a kind of dysfunctional state as you move across the maturation of
the business.
Yancey: You know, I agree with Ian that it would be nice if everyone could be real, but it
is kind of the prisoner’s dilemma sort of situation where all it takes is one person
to not be real and it just ruins it for everybody. I mean, it’s like a lot of people
standing up and saying, ‘these are all things that are wrong with me’ and someone
else stands up and says, ‘All my shit is great, I don’t know what is wrong with
these people. Do business with me.’
Jerry: Right.
Yancey: and that’s just – there is always that.
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Jerry: Right.
Ian: Yeah, the state of equilibrium.
Yancey: So you have to figure out – I mean, it’s funny, on the internet, on Twitter, things
like that, like I don’t really say anything about Kickstarter or talk about what I am
experiencing, I just see no benefit to it. I would like to have the time to be like
writing very open diaries about what is going on, but I just – I don’t know it’s
hard and it’s like high risk. When I do talks and like take Q&As from the
audience, I mean, I don’t know, I don’t hold anything back. I just feel like –
especially if it’s other entrepreneurs or just like younger people in the room, I just
want them understand that yeah, they came here to like hear the Kickstarter guy
talk and I’m the Kickstarter guy, and like have tons of anxiety and you know,
experience a lot of challenging things. I mean, it’s funny, I had a meeting recently
with a guy who does – runs something similar to Kickstarter and he’s been doing
it a lot longer than us and yeah, just really good work, but like not very well-
recognized and we had met because he had – we had met before, but he had
written negative about Kickstarter publically. And so some mutual friends put us
in touch and we met, and he kind of apologized and admitted that he had just sort
of felt jealous about the success or, you know, he just felt like some of the credit
going to Kickstarter, like why shouldn’t some of that go his way, but he was like
open about this and I really thought that was awesome. In the conversation, I was
just – you know, just expressed real gratitude and expressed a real appreciation
for what he has done and you know, but what I wanted to say, but what I didn’t
know how, it was just, yeah, I’d feel jealous if people all the time; you know, I’m
in the same boat just with like, I have my – just as I am something to you, I have
my own versions of that. And you know, it’s interesting, I mean, I think about you
know, what is it, what are the ways to find that sort of – I don’t know, just to not
feel that, to really be able to not feel like everything is zero sum and that someone
else winning means you are losing, and you are holding yourself up to these
unrealistic expectations, like all those things are quite hard and it is quite hard
when everyone is putting out there, an avatar of what their experience is and it is
built around, you know, hyper success and an incredible work ethic. That’s what
everyone is trying to communicate and yeah, so you have a Saturday afternoon
and it’s like well, you know, I kind of just like want to watch basketball and
maybe go for a walk with my wife, but like man, the Uber guy right now, he is
probably learning how to play the cello, and learning Spanish and –
Jerry: No, Portuguese, it’s much different.
Yancey: – and doing meditation with a LinkedIn guy on a jet over Japan right now. Who
am I? And there is just great Franklin FDR quote that comparison is the thief of
joy, because there is always someone better than you and I still don’t have like the
strength to fully not feel that but, you know, it’s gotten better with age, but it is
still there.
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Jerry: I think you are on to something in giving yourself relief from that relentless sense
of comparison which by the way is rooted in this sort of sense of inadequacy that
we are never really good enough. And the thing that I hear you both doing for
each other is being able to laugh about that with somebody who gets it and sort of
cut through things and be able to say, ‘Yeah, you know, this is what I’ve got and
there is a joke’ and you move on and then you go for a walk with your wife.
Ian: Yeah. I think on that kind of subject of being real, I mean, I think Yancey’s point
about prisoner’s dilemma is bang on, and I think that there is like it is an unstable
equilibrium being like super real. I think though, it’s interesting to see how far
you can take it, like I was just thinking about another story on that note which is, I
remember when we were closing our series B rounds, there is a guy who has been
an amazing mentor to me over the years, Greg McAdoo who used to be at
Sequoia and is now doing something quite interesting and something different,
and we had a call where I was really nervous, I was – we were about to sign
everything with Sequoia and I basically knew that one aspect of our kind of
something in our presentation was really good wasn’t actually that good, like the
underlying fundamentals weren’t as strong as they looked. And I’d kind of – I
think, kind of let things get in the way a bit, in terms of that thing being perceived
like a real runaway train and I was really scared I was going to get into a situation
where I had a board member who had – where I had set up a dynamic to
essentially having to create hype rather than just having an honest, open direct
conversation about the true nature of the business. And I went out for breakfast
with him and I took – what felt at that time, like a ginormous risk, because we
hadn’t closed this money yet, you know, it was critical financing for the business
and I just said, “Look, I need to be straight with you about something. This aspect
of our growth is you know, really great for the short term, but I think the
underlying fundamentals are unsustainable and I want to make a bunch of
changes, so if this thing happens then we have a more sustainable, fundamental
kind of driver of this growth.” And he said, you know – and I remember having
this moment of sort of my stomach falling out a bit, and then he said, “Well, you
know, I have already [Inaudible 0:34:43] that and I’m glad you bought it up. Let’s
crack on with fixing it, and I think you are dead right to prioritize that.” We just
moved on and then about I guess, a few months after we closed that round, I had a
call with him, where again, I had just been giving him a bit of bad news about a
few things and I sort of sent him an email afterwards saying, “Hey sorry it was so
much bad news. Hopefully more good stuff on our next call” and he just shot me
this note and he said, you know, “Our job is to deal with the facts as they are and
not how we wished they’d be, that’s what we get paid to do. I thought it was a
great call.” And I think, you know, I do think it’s incumbent on us to push to a
world where you can be real even though as Yancey said, there’s probably some
ceiling on how effective we can be at it, certainly at least when we have any kind
of a real private relationship, you know, I hope you can get there.
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Jerry: Yeah, I really applaud that story. I applaud both of you because he obviously
created the conditions where you could be brave and tell him the truth and the
facts as they are and then his response was ideal. We are planning a bootcamp for
VCs and a couple of my clients have already sort of raised their eyebrows and
said, “Oh my goodness, that’s incredible.” But one of the things that we want to
be teaching is exactly what Andrew said to you, which is that the job of a director,
the job of an investor is to deal with the facts as they are, not as we wish them to
be; and so much dissention and discomfort comes from being in conflict around
that. I love the implicit trust that seems to be in that relationship and extend in
part from you saying the truth and that creates – as we were talking about, the
vulnerability in being able to do that, but it ends up speaking volumes about your
leadership. So, I really, really applaud you for that. You know, we build these
peer groups and we encourage a lot of folks to come together and talk about
things, and one of the basic tenets is this notion of what we call “no fixing” which
we have taken from our kind of patron saint, Parker Palmer, and it’s the notion
that when people come together, there’s no setting the other person straight,
there’s no fixing them; it’s primarily built around the notion of them listening to
each other, and then if advice is sought, advice is given. I don’t know, what do
you think about this notion?
Yancey: Yeah, I mean, I think that your first job is to be like attentive pair of ears for the
other person. I mean, you definitely learn – I don’t know, I think just as a leader,
you learn, you know, just how to be a good listener and how to be really just be
sorting through what someone is saying and thinking about it from a few different
perspectives, both what they are seeing, what you are seeing, what you’ve seen
before and I don’t know, my mind is always immediately like working towards
just trying to see some insights or trying to see it from different perspectives, but I
am also quite confident that Ian is probably already thought about a lot of those
things. But you are just trying to be another set of ears, another set of eyes for the
other person. Sometimes it is just helpful to talk out loud about something. In the
end, you are just like yeah, I don’t really know what I am asking for here; I just –
this is just on my mind and I don’t know where else to go with that.
Jerry: Yeah, and I needed to be heard. Ian, what do you think?
Ian: I enjoy a little bit of tough love, so I sometimes I you know, I like people to sort
of – I enjoy it when people want to like kind of wade in and try and fix my
opinion sometimes –
Jerry: Ian, dude, just fire the guy.
Ian: Yeah, right. I think for me, like I just think there is – I think people will fall into
two fairly distinct camps, I think some people really want to be heard and I think
some people want someone to help them solve the problem and I think you know,
it’s important to differentiate because I do think that sometimes you have a much
more passive role to play and sometimes you have a much more active,
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challenging kind of provocative role to play in helping someone resolve whatever
is going on with them. I would say that Yancey and I tend to be more on the
provocateur kind of end of the spectrum with each other just because I think we
find it fun and I think it almost like – a good example would be the thing that –
the speech that Yancey recently delivered about sort of being a different kind of
company. You know, he sent that to be beforehand as a draft and we talked about
it a bit over the phone, over dinner, and I felt like a more interesting thing for him
there would be to really like take a strong devil’s advocate position on some of
the issues and really play it out a bit because I think he knew that I’d broadly
agree with most of the central tenets, but one of the points I made to him is you
know, a lot of the things you describe about, the idealized company, we kind of
agreed about [Inaudible 0:40:48] things that have already achieved but you
happen to have a unique monopoly in a great market and if you don’t, then the
stuff is impossible. Like maybe you do have to do some tax evasion or whatever
the other things on his list were and you know, I kind of – my view is probably
somewhere in the middle, but I think we are both drawn to provocative ideas
particularly around the domain that we live and breathe, and I think it is fun to
sometimes come and try and shake someone’s view up a bit and that can be as
therapeutic as just someone listening attentively.
Yancey: Yeah, that conversation is one of my more memorable conversations of this year
and it was Kickstarter – we were a week away from announcing that we are
becoming a public benefit corporation and we are putting a lot into this and I was
quite proud of it and so I sent to Ian, what it was that we were going to do and
yeah, Ian just wrote back this like quite critical email that was just like, “You
know, I think this stuff in interesting and good, but I also think that these are
things that you only have the opportunity to do because of your market position
and the expectation of other companies. To do this is wrong” And I suddenly – I
mean, that response hurt me, it hurt my feelings and like it kind of – and it hurt
my pride because here I wanted someone that I really love and care about to say
like “Way to go man, so proud of you!” and here he’s like, I don’t know, this is
cool, but also like maybe this is – maybe you are doing this from place of
privilege and it’s not as legit as you think it is. And he ended up calling me after
that, I think, just because he thought maybe it had been too strong, but it was
actually really helpful for me to just to think about it from a very different
perspective and just to really make sure there was humility around this thing and
that just to not presume certain things about yourself just because we are able to
do that, but no one else in my life talked to me about it that way; no one else, and
I was just so appreciative of that .
Jerry: It’s a beautiful story and it reminds me of something I just said in a coaching
session this morning. I said, you know, “Great coaching isn’t about telling the
client what they want to hear, it’s about telling the client what they need to hear”
and I think that Ian told you what you needed to hear, more than he told you what
you wanted to hear.
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Ian: I mean, I do think a bit of it as just Yancey and I both just like you know, being a
bit cheeky and provocative, you know, but I think it’s just fun playing around
with the real edges of ideas, you know, and I think that is the ultimate shared you
know, shared thing that Yancey and I have is that we are both really drawn to
where there is a lot of intellectual – where you can invest a lot of intellectual
energy and have fun running a business. They are interested in those like, those
edges and I think you know, the nature of those edges is you can, you know, you
can really oscillate on the position and play with things a lot.
Jerry: Well, I really want to thank the two of you for – you know, in a sense I feel like
I‘ve been invited into one of your sessions with each other, and I feel honored and
privileged to sort of watch it unfold. So many of the ways in which you were
supporting each other are exactly the kind of things that I would recommend to
people and I love the fact that – you know, Yancey and I have worked together
for a while, but I love the fact that you guys have each other. And Ian, I have to be
honest with you, now I understand why Yancey is such a good CEO, it’s because
he’s got you. So, thank you so much for doing this. I know that the folks who
listen to the podcast really are going to benefit from this kind of dialogue and my
hope in having this conversation is that they – whether it’s formally or informally
that each of them find an Ian or a Yancey in their life, and that they really grow
and benefit from that. So, thank you for taking the time.
Ian: Thanks Jerry.
Yancey: Cool, thanks Jerry.
**
That’s it for our conversation today. You know, a lot was covered in this episode from links, to
books, to quotes, to images; so we went ahead and compiled all that, and put it on our site at
Reboot.io/podcast. If you’d like to be a guest on the show, you can find out about that on our site
as well. I’m really grateful that you took the time to listen. If you enjoyed the show and you want
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you’re there, it would be great if you could leave us a review letting us know how the show
affected you. So, thank you again for listening, and I really look forward to future conversations
together.
[Singing]
“How long till my soul gets it right?
Did any human being ever reach that kind of light?
I call on the resting soul of Galileo,
King of night-vision, King of insight.”
[End of audio 0:46:59]
[End of transcript]