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Reboot Podcast #30 - Who Do You Turn To? - with Yancey Strickler and Ian Hogarth

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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.

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Reboot Podcast #30 - Who Do You Turn To? - with Yancey Strickler and Ian Hogarth

  1. 1. Reboot030_Who_Turn_To Page 1 of 13 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
  2. 2. Reboot030_Who_Turn_To Page 2 of 13 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
  3. 3. Reboot030_Who_Turn_To Page 3 of 13 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
  4. 4. Reboot030_Who_Turn_To Page 4 of 13 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
  5. 5. Reboot030_Who_Turn_To Page 5 of 13 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
  6. 6. Reboot030_Who_Turn_To Page 6 of 13 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
  7. 7. Reboot030_Who_Turn_To Page 7 of 13 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
  8. 8. Reboot030_Who_Turn_To Page 8 of 13 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.
  9. 9. Reboot030_Who_Turn_To Page 9 of 13 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.
  10. 10. Reboot030_Who_Turn_To Page 10 of 13 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.
  11. 11. Reboot030_Who_Turn_To Page 11 of 13 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,
  12. 12. Reboot030_Who_Turn_To Page 12 of 13 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.
  13. 13. Reboot030_Who_Turn_To Page 13 of 13 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 to get all the latest episodes as we release them, head over to iTunes and subscribe and while 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]

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