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Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
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Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
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Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
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Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast
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Reboot Podcast #27 - From Caring Comes Courage - with Jerry Colonna on Reboot Podcast

  1. Reboot027_Caring_Comes_Courage Page 1 of 16 Today’s episode is brought to you by JustWorks. JustWorks helps businesses take care of their benefits, their healthcare, payroll and HR. It’s just that simple. We use it and absolutely love it here at Reboot. Grow your business and not your busy work. Get JustWorks. To learn more and to learn how we use it at Reboot, go to Reboot.io/justworks. ** “The stupid-ass startup playbook tells you that there is no place in your company for love. And I’m here to tell you, that’s a lie.” Welcome to the Reboot podcast. “From caring comes courage.” – Lao Tzu. I was kind of a nerd in high school. Okay, I was a nerd in high school. There are a lot of reasons you could have called me a nerd, but a big one was my love for the stock market. Thanks to a small inheritance from a great aunt, trusting parents, an old Sky pager, and a booming internet tech stock bubble, I was actively trading stocks while in high school. My friends used to tease me for checking the NASDAQ and the Dow, sneaking looks during class on the pager, and calling my broker at lunch to buy into whatever was hot at the time; maybe it was Yahoo or SISCO or maybe Juniper Networks and hey, I was good and very lucky, or probably just lucky. But it works for me, so much so that I often heard from friends and even random kids at school that I was going to crush it, that I was going to figure it out and be very successful at a young age, and that felt really good at the time, but it also carried a weight. With each passing year that I didn’t crush it, every word of support, every vote of confidence became a burden of disappointment. By the time I was 28, the comments no longer perked me up, but amplified and supported the voice of doubt. I remember feeling like a fraud, feeling I let all those people down. Frankly people I don’t even talk to or see anymore, but their voice still echoed; they believed in me probably more than I believed in myself. Were they wrong? Did I lie to them? Did I just really screw it up? Their support from the past fuelled my own disappointment today. It’s really 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. Our guest today, a podcast listener and entrepreneur is Zoe Weintraub, founder of Opus for Work. Zoe and Jerry discuss both the beauty and the burden of external expectations. We ultimately find that when you follow the emotion and the vulnerability associated with them, they expose your super power hiding in plain sight. Jerry: Hey Zoe, how are you? It’s good to connect with you. Zoe: Hey Jerry, thanks so much for having me on the show; such an honor, so happy to be here and talk with you today. Jerry: Oh well, it’s really a pleasure, and anybody who emails me and tells me they are a huge fan of the show gets immediate buy right into the show.
  2. Reboot027_Caring_Comes_Courage Page 2 of 16 Zoe: Well, the emails, they work. Jerry: That’s right, they do, especially if you flatter somebody’s ego. No, I’m teasing. So, it’s really a delight to meet you and talk with you; why don’t you just take a moment and tell us a little bit about who you are, what your company does and really in the end, like what prompted to reach out in the first place? Zoe: Yeah, sure. So, my name is Zoe, I’m the CEO and co-founder of Opus for Work and we’re basically a company pursuing the idea of empowering people to work when they want, and to work flexibly. So, we believe that people are seeking a new way to work and that is fundamentally changing, and so we want to be the place that someone can go to educate themselves about flexible work opportunities, find those jobs, and then manage those opportunities so that they can increase their earnings over time. We’ve started kind of, today in the space of on-demand jobs in the Bay area, and we are really looking at how to help people find these jobs, make more money, and then build a reputation that they can use to kind of grow their career in and outside of part time or full-time, temporary work. And my background before that is, I worked in startups, very different, I worked at payments at WePay, and then Grouper, which was a group matchmaking dating company. So, in a way, we are helping people make more money, but also matching them to the right opportunities, and we really see that you know, there’s this great chance for people to have a life in which they have work come as a secondary component, and I think on-demand jobs are kind of the first opportunity. People have seen that in the consumer space, and that it’s going to translate into a lot more industries over time, and so we are kind of betting on helping people make that work. Jerry: Gotcha. And the name of the company is Opus for – tell me a little bit about that. Zoe: Yeah, so Opus kind of came about in a couple fo ways. So, me and my co-founder Zach, who I mentioned, we are both really – Jerry: Oh wait, it’s Zoe and Zach? Zoe: Yeah, and [Unclear 0:06:01] Jerry: Yeah. Zoe: We contemplated a name with our letters in that, but we thought it was a little too self-centered. So, we had worked together at Grouper, and we decided when we left, we wanted to start a company around people. Being in the Bay area, a lot of companies spawned out of great products or great ideas, and we have a lot of those and we wanted to help people. We thought that building a foundation with you know, people at the start would help us explore a bunch of different ideas. So, doing that, I needed to make money while we pursued some ideas, and one of
  3. Reboot027_Caring_Comes_Courage Page 3 of 16 those ways was working for on-demand services. So, I started working for Instacart, Sidecar, Caviar, and just really saw a totally different lens into the types of people that were doing these jobs, and the reasons why they were doing them. I was an entrepreneur, that was why I was doing them; someone was a stay-at- home mom, that was why she was doing them; someone that was retired, needed extra income; all these different reasons and I really saw that people loved it. They loved the freedom, the flexibility and it was empowering, and they think you know, now – that was last November and so eight-nine months later, we really circled in on opportunities and jobs, or the way that you can first help people experience that, but over time as more and more industries adopt this model, like how do you provide the base and the community for people looking for this work. And so that was really exciting to learn about you know, different income classes, different skill sets of people in the Bay area where there is such a dichotomy between high skilled and low skilled, and that gap is only widening. Jerry: Gotcha. That’s really helpful. So, take me to what it is that prompted you to reach out in the first place. Zoe: Yeah, so as I mentioned, I am a big fan of Reboot. I listen to it, whenever you release an episode, I usually run, and I have the lovely Golden Gate Bridge as my backdrop, so that’s very serene. I was thinking, you know, what is it that I personally am trying to work on and developing this company, and I think learning is such a big part of it, and that was one of the reasons why we wanted to undertake it as where can we learn the quickest, and how do we do that and you know, having someone that I fully trust and being supportive as a co-founder has been great to take that risk and that leap. But I was thinking about you know, I am okay with failure because I think it’s a great way to learn, but what about all the people around me that have given me the strength and the confidence to pursue something completely unknown and take this huge risk? What about their, like conception of failure, because now they are so tied to my success and to my journey, and what does that mean for them and how do I share my learnings in a way that impacts them in a meaningful way, but then also doesn’t hurt them too? I mean, what if I do fail? Is it a reflection of them and you know, their belief or their risk or them putting their neck on the line for me in an introduction or an investment, or a Facebook post? So I was just thinking more about those implications and how to bring people along on the journey in a positive way, but then also to protect them from whatever potential happens to me and this company, down the road. Jerry: Okay, so let’s name a few things that’s going on already. Zoe: Okay. Jerry: What was the last phrase you just used? Zoe: Down the road?
  4. Reboot027_Caring_Comes_Courage Page 4 of 16 Jerry: Just before that. What verb do you want to use as it relates to them? Zoe: Affect – how it affects them? Jerry: This is so funny – Zoe: I can’t go back – Jerry: I know, all the listeners are hearing it. You want to protect them. Zoe: Oh yes, okay. Jerry: Oh yes. Zoe: Yeah. Jerry: Tell me about why you need to protect them. Zoe: You know, I think the protection is that – Jerry: Yeah, so just slow down – Zoe: Yeah. Jerry: – because it just happened. Zoe: Yeah. Jerry: Your whole face shifted again. Zoe: Yeah. Jerry: What does protecting them mean? From what? Zoe: Well – Jerry: Yeah, now you are feeling it. Zoe: I don’t know. I think, failure, or lack of meeting my potential, or their set expectation for my potential, maybe. Jerry: Yeah, I don’t know, the answer is not here. Zoe: No.
  5. Reboot027_Caring_Comes_Courage Page 5 of 16 Jerry: And you did this wonderful thing with your eyes, you just shifted your eyes up into the right, because that’s where the answer is. The answer is actually inside of you. So, what is it that you think you are supposed to protect them from? Zoe: Hmm. Jerry: How would it feel if the company fails? How do you imagine they would feel? Zoe: Would they would feel disappointed or let down? Jerry: I don’t know, you ask yourself that question. What do you think they are going to feel? Zoe: I guess, I don’t know if I’m going to go around it, but I think it’s, when you put yourself behind someone and you support someone and you, you know, attach your name to that, then it’s part of their identity. And so protecting them from a part of their identity that they have entrusted me with, and then that fear that they even entrusted me with that and then what happens if something happens to it. Jerry: Yeah, so can you name the feelings that you are feeling right now as you are saying all that, because your lip is quivering. Zoe: I think like uncertainty; like I can’t give them any certainty about that part of themselves that they have shared with me or that they have - Jerry: The trust that they have placed in you. Zoe: Yeah, exactly; the trust. Jerry: Yeah, so notice what that does for Zoe as the person. Zoe is okay with failure, Zach is okay with failure because Zoe and Zach, they are good; right? Zoe: Yeah. Jerry: Right and I wish that our listeners could see the smile on your face when I say Zoe and Zach are good because you feel that. Zoe: Yeah. Jerry: But there’s a whole another layer here, which is, there is a whole group of people putting their lives to the side, their ability to earn a reasonable living, maybe even they have to take a job at Instacart, in order to keep the job at Opus, and what if you and Zach fail the people who placed their trust inside of you? Zoe: Yeah, that’s it.
  6. Reboot027_Caring_Comes_Courage Page 6 of 16 Jerry: That’s a big piece. Zoe: I think I was – I was thinking about it in like this scale or the spectrum of that trust that’s been put in us and in me, and in one side there’s family and friends, and there’s you know, angel investors, and then there’s eventually VCs, and then hopefully eventually there’s paying customers. But then there’s a way to share that, but then there’s really the people. Jerry: The people, yeah. Zoe: And I think that being so, like emotional linked to them makes it harder too. Jerry: Yes, it does because – now we are going to go out on a limb here, right? Zoe: Okay. Jerry: And I really appreciate your bravery here, and I’m going to say something out loud: people who have been fans of this show for a long time, people have seen me do this work understand one thing and one thing only; what I ask clients and people that I encounter to do is to authentically step into their fullness of themselves, including the soft, tender spots because that is where our strength as leaders lies. Zoe: Yeah. Jerry: So, in the past, have you ever been disappointed by someone that you placed trust in; a boss, a friend, a parent, all of the above, none of the above? Zoe: Yeah, I think all of the above. Jerry: All of the above? Zoe: Yeah. Jerry: Right and how does that feel inside? Or, how did it feel when that trust was either broken, or that you had the sense of disappointment and let down? Zoe: You know, I think you feel – I think initially I feel – you feel down or – Jerry: You feel taken advantage of, perhaps? Zoe: You feel taken advantage of, and you feel disillusioned, I think, is the after effect that – Jerry: Like, “What an idiot I am.”
  7. Reboot027_Caring_Comes_Courage Page 7 of 16 Zoe: Yeah, like you couldn’t see that, or you couldn’t see what was right in front of you, or you had those doubts and you didn’t listen to them. Jerry: Right. Zoe: And it’s then rebuilding either that place for that person, if you forgive and move forward, or it’s refilling that with something else and that sense of, you know, part of you is empty or because you would trust in someone, or you would let that someone be a part of you and your own identity. Jerry: Okay, so it’s a deep, deep wound that happens. Existentially we start to question our own worth, “What the hell is wrong with me that I could trust this person?” or even worse, “I saw all the signs and I blew right past them. I still trusted this person.” Zoe: Yeah. Jerry: We start to really undermine our own sense of self when that placed trust turns out to have been a source of disappointment, because we don’t actually know fully if it was misplaced. Zoe: Right. Jerry: Sometimes it’s clearly misplaced. Sometimes it was placed for good, healthy reasons, and we are still disappointed. We are born, programmed to trust our parents. Zoe: Yeah, we are. Jerry: And as a parent, I will tell you that one of the inherent attributes of parenting, the parent-child relationship is wounded. There is no way around that. That’s what happens. When we place love and we act in love in our relationship, we are signing up to pain and disappointment. Zoe: Yeah. Jerry: That is implicit in the relationship. Zoe: Yeah. Jerry: So, it may not have even been an example of our being naïve or foolish, it may be simply a consequence of relationship. Not all relationships disappoint all the time; if they do, it’s probably not a healthy relationship. Zoe: Yeah.
  8. Reboot027_Caring_Comes_Courage Page 8 of 16 Jerry: But all relationships will disappoint at some point. Zoe: Yeah, and it’s accepting that. Jerry: That’s right and not using it as fuel for your own self-denigration. Zoe: Right. Jerry: So, let’s hold that for a moment and just acknowledge the burden of – bring about the people who put their faith and trust in you, and then potentially disappointing them through the failure, because even the investors, there is a great a great line, that I want everyone who is listening to remember this: accredited investors. Zoe: Mm-hmm. Jerry: You know what that means? It means they can afford to lose the money. So, I don’t want anybody listening to this to worry about losing money for accredited investors. The problem is when mom and dad take the second mortgage in the house – Zoe: Yeah. Jerry: – because they are actually not an accredited investor. When you have to borrow money to invest, you are not an accredited investor. Zoe: Exactly. Jerry: You may be an accredited parent, you may be a great parent coming from a pure place of love and belief, but that is not investing. So, there is that group of people, there is – and you named it well, potentially customers, as all these people around us. So, like we say to ourselves, I can role a failure except for the fact that I care about all these people. So, here’s a little thing I want you to hold on to; the fact that you care about people is a super power Zoe. Zoe: Okay. Jerry: The fact that you care is hard, but like every great Marvel DC comic superhero, their super power can have a dark side, and what you are really identifying here is that your super power. I don’t know Zach well enough but if he is your partner, I guarantee you, he cares about people too. Zoe: Yeah, I’d say equally if not more. Jerry: Because the strength of you as a CEO is so evident that if he’s going to be your partner and you allow him to be your partner, he’s going to have shared values.
  9. Reboot027_Caring_Comes_Courage Page 9 of 16 Zoe: Yeah. Jerry: But that super power, I’ll show you how that’s a superpower in a second, but that super power is your tender spot as well. Zoe: Mm-hmm. That makes a lot of sense. Jerry: Here’s a very male example; okay, Superman comes from out of space, and because he comes from out of space, he has a very special relationship with the Sun. That is both his strength and his weakness because if you block the sunlight, he gets weak. This is geeky stuff. The geeks on the [Crosstalk] Zoe: I didn’t make many trips to the comic store but I’ll go with it, I like having a super power. Jerry: And I will forgive you, because we at Reboot refer to ourselves as ‘The Avengers’ and I get to be Iron Man, which is great. Zoe: I can see that, that was [Crosstalk] Jerry: That’s right, Dan Putt is ‘Captain America’. So, you know, he’s like, “Language Jerry, language.” Okay, so let’s hold this for a moment; the tender spot shows up in ‘what if I disappoint?’ You know where the super power comes from? Tell me again, what the purpose of this company is. Zoe: To empower people – Jerry: To empower who? Zoe: People. Jerry: So, you mean, when you were working at – what was it, Instacart? Where were you working? Zoe: Well, I was working for a few of those; Instacart, Sidecar - Jerry: And remember the stay-at-home mom who was working there, right? Zoe: Mm-hmm. Jerry: Remember the retiree? Zoe: Yeah. I remember all of them by name. Jerry: Now you’re going to make me cry, girl. That’s your super power.
  10. Reboot027_Caring_Comes_Courage Page 10 of 16 Zoe: Yeah. Jerry: You remember all of them by name. Zoe: It’s scary to think of the day when I won’t, which I hope doesn’t happen. Jerry: Right, you can always hold them in your heart even if you can’t remember all the specifics. Zoe: Yeah. Jerry: What do you remember about them? Zoe: I remember, you know, why they liked what they were doing, but why it’s so much better for them outside of work. So you know, someone that has eight more hours a day, or eight more hours a week with their kids, or they can take care of their parents that are ageing, or a veteran that can’t get back to the line of work because they have been out of it for X number of years, or people that have a smartphone and don’t realize all that it’s capable, like all that’s at their fingertips and you just have to you know, show them how to download an app or – Jerry: Why is it so important Zoe for you? Why is it so important for them to have a better life, or for their children to have a better life? Zoe: I think it’s important because I think I’ve always been someone who feels like you can educate people to empower them, and I feel as though I possess a lot of knowledge about this space and the potential, and how this helps people. And so, I want to empower them with this knowledge, so that they can make their own decisions about their life, whereas you know, I think most people make decisions about their life based on their jobs and not the other way around. Jerry: Yes, and you said something that was quite revealing. You said, “It’s always been important to me.” That ‘always’ tells me a lot. Yeah, it tells me about your childhood. Zoe: Yeah. Jerry: And it tells me about going to school, and it tells me what kind of a friend you’ve been, and it tells me what kind of daughter you are, and it tells me what kind of sister you might be, and it tells me what kind of cousin – the care for the empowerment of other people, yeah, is a major motivation. Zoe: Yeah. Jerry: Right, and it is part of what defines who you are as a person.
  11. Reboot027_Caring_Comes_Courage Page 11 of 16 Zoe: Absolutely. Jerry: And this, my friend, is your super power. Zoe: Oh, that’s a tough one. Jerry: What’s tough about it? Zoe: Well, just that you are linked to so many other people’s empowerment, and that is what empowers me that you feel all that. Jerry: Yes. What’s the alternative to feeling all of that? Zoe: I don’t think there is one. Jerry: Right. To me, the word that pops in my head is, it’s a kind of death. Zoe: Yeah. Jerry: For someone like you, and I’m just beginning to get to know you, but for someone like you, feeling that connected, feeling that powerfully connected to other human beings, is like Superman needing to be in the sunlight. Zoe: Yeah. Jerry: Right? Zoe: Absolutely. Jerry: Right and so – I’m going to go out on a limb here, you are living in the belly of the beast in the tech community. Zoe: Yeah. Jerry: And you are daily bombarded with messages that say, focus on the intellect, focus on the business case, right? Zoe: Yeah. Jerry: You know the messages you get; the stupid-ass startup playbook tells you that there is no place in your company for love. And I’m here to tell you, that’s a lie. In fact, I’m here to tell you, that anybody who doesn’t think that Steve Jobs loved certain aspects of the products is denying the reality of his genius. He is a very complicated character, and I like focusing on Steve because Steve is this bizarre, polarizing icon.
  12. Reboot027_Caring_Comes_Courage Page 12 of 16 Zoe: yeah. Jerry: But this is the part that you, and probably Zach as well, love and this is what led you to create the company in the first place. Tell me again, the name of the company? Zoe: Opus. Jerry: And what does Opus mean? Zoe: A composition of work. Jerry: Not just a composition of work; your greatest composition of work. Zoe: Yeah. Jerry: The aspiration that is implicit in the title of this company, is to be, dare I say it, you and Zach and all of the team’s greatest expression, greatest heart-centered artistic expression, which is in helping empower people. Zoe: Yeah. Jerry: How’s that for a mission statement? Zoe: That’s a really good mission statement; I think we will have to quote you on it. Jerry: Well, it’s a good thing we are recording this, because I can never remember what I say. Zoe: Me neither. Jerry: Imagine asking people to come work for that company. Zoe: Oh, I can’t wait. I’ve been – we’ve been talking to several engineers for technical lead positions, and I am reminded every time I have a conversation, of not only why I started this company, but how exciting it is to be able to bring people into that mission, and the potential to do that is incredible. Jerry: Now, imagine those people, for a brief period of time, worked for Opus and then Opus fails; will they feel pain? Zoe: No. Jerry: Well, I think they’ll feel the loss. Zoe: Well, the money, yeah, the income maybe.
  13. Reboot027_Caring_Comes_Courage Page 13 of 16 Jerry: And they’ll feel the loss of it not having worked. Zoe: Right. Jerry: We just finished up on our most recent boot camp, alumni boot camp, and someone said, “Now I get, viscerally, what does it mean when I hear the line, ‘better than to have loved and lost, than never to have loved before’.” Better to have experienced a work environment that strives to empower people to empower people, than to work for yet another company whose main mission is to optimize hours in order to create profitability. Zoe: There’s no learning there in no matter how short or how long it is; it’s that opportunity to learn. Jerry: That’s right, and the opportunity to experience that that maybe possible. You know, as we often talk about at Reboot, in describing our own work, but in really describing what we wish for people, it’s “Good work, done well, for the right reasons.” Good work done well, so that you are profitable – nothing that we are saying here, takes you out of the obligation to create a self-sufficient, self- sustaining machine, called the company. Zoe: And the right reason is the intention. Jerry: That’s right. The right reasons are everything. You know, many people know I’m a Buddhist and we often talk about Buddhism, and to me Buddhism’s core teaching is what is known as the four noble truths. The truth that life is filled with suffering, the truth that what we do to push away suffering increases suffering, the truth that the cessation of suffering, there is way out, ‘cause if not, you might as well kill yourself; the truth of the fourth noble truth, which is the eight-fold path towards the reduction of suffering. And to me the most important step in the eight-fold path is right intention. What are you up to? Why are you doing this? What is my intention? The example I often use is, a man plunges a knife into the chest of another man; is it a good act or a bad act? He’s a surgeon, who happens to be robbing you, because he’s trying to feed his children. Right? I mean, intention defines so much of what we are about and so your intention is to empower your employees, to empower other people, so that they can go home and spend time with their children, or finish their college degree, or pay off, you know, their student loan debts. That’s your intention. Zoe: Yeah. Jerry: That’s noble. I can’t tell you if it’s a good business. Zoe: I can’t yet quite either, but I hope that I can and I think that’s the bet and the hypothesis that we are making, is that that intention can create a sustainable
  14. Reboot027_Caring_Comes_Courage Page 14 of 16 business and that the intention of the people that work for it and the intention of what it’s doing to the economic landscape, or how people look at work and how people look at – and how they then want to hire for their companies, that it can carry through. Jerry: Yeah. So, I’m feeling quite paternalistic right now and – which is funny because I’m always feeling paternalistic, that’s an issue that I am dealing with. So, I’m going to speak more advising than coaching in a moment, and this speaks to the implicit question, I think you were asking, which is, “How do I survive when I care so much?” Does that resonate? Zoe: Yes. Jerry: So, here’s how you survive and here’s what it’s about in terms of this – what we often talk about is a greater resiliency. I don’t care if Opus succeeds or fails, so we never lose connection to your core purpose. The truth is, every single one of our entrepreneurial endeavors is like an art project; some turn out well, some don’t turn out so well. Zoe: Yeah. Jerry: A few years back, I was very reluctant to scale myself as a coach because, well, I still have all this ambivalence about I never want to lose what’s happening for me right now, which is the ability to have a deep, meaningful conversation with one human being. No matter how famous I might become, or how many people listen to the podcast, the thing that motivates me more than anything else that makes my heart sing and gives me nourishment, is to have a meaningful conversation with one person. So, in that ambivalence, I drafted a bunch of people, including Dan Putt, to launch this business called Cojourneo, and Cojourneo was trying to be a platform for this kind of work, with a couple of digitized things, maybe an ad, maybe online learning platform and all this stuff, but we never really got it right. And I took – we took some of the best intentions of that, some of the best wishes and poured that into this remarkably successful, beautiful, stable business called Reboot. Zoe: Yeah. Jerry: It’s the same conversation. It’s the same work. I have been doing the same work most of my adult life, regardless of the expressions as a career. So, whether Opus raises it’s rounds, whether you hire – my lips to God’s ears, you hire all the people that you want to deal and you give heart and soul to Uber, that’s great, but whether or not you succeed in doing that, hold on to this, this is your super power. This will define you as a leader, and we will know it, because people will give up safety and security to belong to the company that you created. Zoe: Thank you.
  15. Reboot027_Caring_Comes_Courage Page 15 of 16 Jerry: You are welcome, and thank you for leaning in with such bravery and honesty and depth here. I think you really named a very, very important topic. Before we go, anything else that you would want to say or add? Zoe: You know, I think that you’ve helped show how important vulnerability is, in all aspects of starting a company, not just through your podcasts, but even just speaking with you today. I think, you know, as someone that does want to empower people and help people and connected to that, vulnerability is a way in which you can always do that, but you can sometimes place it in a different buckets. Jerry: Yes. Zoe: And I think self-vulnerability and you know, figuring out how to improve upon what you are feeling, and dig into that, is something that I sometimes push to the side in hopes of connecting more with users or with friends or with family, but they are one and the same, and so I appreciate you digging into that. Jerry: Well, thank you for that. What I would add to that is, for me the goal isn’t necessarily vulnerability. The goal is authenticity. The goal is being real. It can be experienced often times and expressed often times as a kind of tenderness and vulnerability, and the reason for that is, behind so much of our fear is sadness. And so it comes out, it gives us a sense of being exposed, “Uh-oh, I’m going to be judged, I’m going to be criticized, someone is going to listen to this, they are going to question whether or not I have the strength, because I just cried” but what I really want to encourage everyone to do, is show up in the totality of who they are and lead from that place. Sometimes, that is from a vulnerable, tender place, and sometimes it’s from a completely joyous, completely hysterical, completely goofy place. What people want is to connect with authentic human beings. That’s what we want our leaders to be. Zoe: Yeah. Jerry: We don’t want them to be fake. We want them to be real, even if that means they come across as broken. Zoe: Yeah. Jerry: Anyway, I really appreciate that last question, because I think it gave us an opportunity to explore something that a lot of people often feel. It’s like, “Oh, I can’t come on the show because I might cry.” Come on the show and laugh. Come on the show and show us how you are kind of – don’t take yourself too seriously.
  16. Reboot027_Caring_Comes_Courage Page 16 of 16 Zoe: Yeah. That’s something that definitely is undervalued in the trials and tribulations of starting a company; is laughter. Jerry: That’s it. Thank you so much for coming on the show. I know people are going to really, really enjoy this episode. Thank you, Zoe. Zoe: Thank you so much, Jerry. ** Meet the co-founders of Adcade. Rob Prentice, the COO of Adcade. Rob Cromer, CEO of Adcade. Buzz Wiggins, CTO of Adcade. There was a group consensus that our relationship was not as healthy as it was when we started the company; just kind of casualties of running a business. The first thing to go is the communication between best friends, and there were things we needed to unpack, and we did not have the environment here to do such an exercise on our own. Let’s say we didn’t have the framework. Didn’t have the framework; and it’s not to say that we haven’t done things that bother each other since the boot camp, but we made it like a point to sit each other down, and just say it so you don’t build up resentment, you don’t feel as though you’re holding something in. You just sit them down, have a conversation about it, tell how you feel. I think that goes a long way, and it’s something that we would never have done before naturally. Co-founder boot camp is our invitation for you to discover how your leadership team can work together, better. Join us this March 2nd through the 6th. Learn more at reboot.io/co-founders. ** So, 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 0:41:04] [End of transcript]
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