#18 The Reboot Podcast - Claim Who You Are As a Leader

Reboot018_Claim_You_As_Leader

Welcome to the Reboot podcast. We’re proud to say that today’s episode is brought to you by Justworks. Justworks helps businesses take care of their benefits, healthcare, payroll and HR. It’s super simple and powerful. We use it and we love it. And this podcast really is way more than just Jerry so we wanted to take this opportunity to introduce you to more of our team, and hear their experience in using Justworks.

Ali Schultz: I’m Ali Schultz, and I am the COO of Reboot. Justworks makes my life insanely easy. It’s every HR solution I have ever wanted in one place including my benefits and I don’t have to think about HR things at all.

Dan Putt: And how does your experience with Justworks compare to other providers that you may have used in the past?

Ali Schultz: I have tried two of the largest HR solutions in the market, and the time that it has taken out of my life, to use both of those programs, is maddening to me. Back then, at least a couple of years ago, I remember thinking to myself, ‘This really doesn’t need to be as complicated as it is’ and I was hoping that someone would create what Justworks has created. I feel like it has kind of given life and a new-found sense of joy and freedom to HR professionals around the globe.

Dan Putt: Well, you hear how much Ali loves Justworks and a happy Ali is a happy Reboot. If you are ready to grow your business and not your busy work, head over to Reboot.io/justworks. You’ll find out more about how we use Justworks and how it could work for you. That’s Reboot.io/justworks.

“Suppose what you fear could be trapped and held in Paris. Then you would have courage to go everywhere in the world. All the directions of the compass open to you, except the degrees east or west of true north that lead to Paris. Still, you wouldn’t dare to put your toes smack-dab on the city-limit line. You’re not really willing to stand on the mountain side, miles away, and watch the Paris lights come up at night. Just to be on the safe side, you decide to stay completely out of France. But then danger seems too close even to those boundaries, and you feel the timid part of you covering the whole globe again. You need the kind of friend who learns your secret and says, ‘See Paris first’.” That poem is called ‘See Paris First’ by M. Truman Cooper.

Fear is a familiar and powerful co-founder in startups. We do our best to quiet it, shut it down, deny it; perhaps our biggest struggle with it is simply acknowledging it. What if you not only acknowledged your fear but leaned into it? What if you let go of your own hope to control things, and go back to building and leading from a place of love? Jules Pieri, Co-Founder and CEO of the product launch platform, ‘The Grommet’ has done just that for her growing team of 55 employees. In this conversation, Jules and Jerry discuss what it was like to embrace the grit of a Detroit, working-class upbringing, face head-on the fears of being a non-prototypical entrepreneur and building a new kind of company in one of the scariest economic times in recent memory. Through it all, Jules has been able to move forward with courage to build an organization where people can feel loved and do great work in the process.

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Jerry Colonna: Hi Jules, it’s really great to have you on this show. Thanks for coming on. Can you take a little bit of time and tell us a little bit about yourself and the company? It’s called ‘The Grommet’, right?

Jules Pieri: Right, I’m the Co-Founder and CEO of The Grommet. It’s my third startup, first to found. My background is, I am an industrial designer and I worked in a couple of startups and a bunch of big brands. And I saw something happening that just kinda made me mad, which was the best products did not win even when I worked in big brands; and I wanted to fix that. So, fast-forward to 2008, The Grommet was born. So we’ve been launching products, one a day, ever since then and built a pretty massive community that really is the strength behind what we do. We’ve launched some products that now are household names like Fitbit, and SodaStream, and your startup listeners all probably have IdeaPaint on their walls.

Jerry: Mm-hmm.

Jules: Right now, we are looking at a panoply of internet of things, you know, really cool things that are harnessing data with physical products. So, we’re always kind of discovering the future.

Jerry: I love that; I was a user of Fitbit, this is a sort of a shout out to our friends at Fitbit because using Fitbit, it prompted me to lose the last 30 pounds that I wanted to lose.

Jules: Congrats.

Jerry: Yeah, and so I'm a big fan of a lot of the products that you have already talked about. I also – I have to tell you, I’m a fan of something else which is this notion of ‘Citizen Commerce’.

Jules: Oh yeah.

Jerry: Tell me what that means, yeah.

Jules: Well, it was a term born in my kitchen one day. I had been wandering around for about a year trying to think of a phrase on and off, that captured the movement that I thought was forming, which is bigger than our own business. And I watching citizen journalism in particular where people really, like yourself, are shaping the media, forming the media. And I thought, you know, our business which was already operational at that point, was taking this role of making markets for worthy companies and products, people whose values we could align with. So, those two words kind of came together and I trademarked them, ‘Citizen Commerce’ and for the average person, I think of it very simply that a lot of our budget is fixed but there’s probably about 10% we can really play with and devote those dollars almost like votes, against seeing the change we want or the companies we want to succeed. And even though I am an industrial designer,

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ultimately I realized that business was my true craft and business is the most powerful entity on Earth. It trumps non-profits, governments, educational institutions. So we need to expect more from business and we can and we can do that very simply by supporting the companies that represent what we want the world to be.

Jerry: It’s beautiful, you know, I recently did a talk here in Boulder for Boulder Startup Week and I was joined on stage –

Jules: You were in Boulder? I was just there.

Jerry: I am in Boulder.

Jules: I was just there; I spoke five times at the World Affairs Council.

Jerry: Oh, fantastic.

Jules: Conference on World affairs.

Jerry: Yeah, so I actually serve as the chair of the board of trustees at Naropa University, the Buddhist University here in town. And so we had our board meeting and graduation this past weekend, and I did the keynote for Boulder Startup Week. And I was drawn by Matt Stinchcomb, who was one of the early employees at Etsy.

Jules: Yeah.

Jerry: And he spoke a lot about the beautiful book by Charles Eisenstein, which is, ‘The More Beautiful World Our Heart Knows Is Possible’ and it’s really about imagining that world that is possible and I loved your notion that – ‘cause I share the same belief that business can be a force for good. As I said the other day, you know, for 150-200 years of the industrial revolution, the basic premise has been to take raw material, and turn it into wealth for a few individuals. And what if we turn this engine into something else? Into something – and this is something we try to focus on at Reboot. What if businesses were an opportunity for the full self-actualization of the people who participate? What if the things we try to bring forth into the world are generative to the world and not taking from the world, not consumptive of the world?

Jules: You sound like the founder of Stonyfield Farm. Have you read any of his stuff? I haven’t but I love the yogurt.

Jerry: It’s the same idea that so much of businesses take from the planet, taking from competitors, taking from employees; I mean people don’t use those words but ‘competing’, in its essence, has some of that flavor. And he says the exact same thing, ‘Why could business be additive? Why does it always have to be

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subtractive?’ It’s very much how he’s built the business and then there’s a sidebar to that that I read in something more recently; I'm sure a lot of your listeners have been reading or have read Ben Horowitz’s book, ‘The Hard Thing About Hard Things’ and the most – kinda glistening gem I’ve picked up from that book was something he was – which was one of his mentors said to him, ‘No matter what the commercial success of a company or a failure, it’s still an end in itself to build a good company’. I stood in front of my team recently and talked about that because at the end of the day, at least in my life and many of our lives, it’s where we form some of the most meaningful relationships; our sense of self, our capabilities, possibilities, where we learn, where we spend all our time and of course, every company wants to succeed on all the conventional dimensions. But this was fresh thinking to me and it kind of affirmed things that I do all the time, to build a good company. And I actually don’t do it just to be competitive, just to make sure we have the best team. I do it because there’s a joy in it that I’m responsible for people’s lives, I’m CEO of a company, I’m responsible for an aspect of their lives and I take that – I take that as a – it is a responsibility but it’s not heavy, it’s a joy. I can influence these people, we can influence each other and so we spent, in this company, a lot of time making that time we spent together, ultimately building a good company, whether or not ‘The Grommet’ is the one that endures and wins, if you will. We already did because I’ve formed – we’ve formed together, our lives in a way that I think is healthy.

Jules: I love where you’re going with this because what I take from what you are saying is that you’ve defined success in a much broader way than the conventional view.

Jerry: Yeah.

Jules: And that success has more to do with, in some ways – these are my words and not yours obviously, but this is a question that I often put to clients which is, ‘What kind of company do you want for?’ Or more specifically, ‘What kind of company would you like your child to come to work for?’

Jerry: Yeah, this is the key; I have three sons and they are all college to entering-the-workforce age and that’s why I know this. That’s why I know this is important.

Jules: What do you mean? Say more.

Jerry: I’ll back up a little bit. My career has tracked my children’s lives in an interesting way. I worked – when I worked for big companies, I worked for Meg Whitman and I first worked for her at Keds, the shoe company, and another shoe company Stride Rite, and then Playskool, the toy company. And my kids were growing up through the product set during that time and we also sold to mothers and parents. So that was super-useful; I just was in the mix, in the flow always of what we were trying to do and succeed at. I was always ahead of the pack. I had to be, just to live my life. And then, this company, fast-forward to today, we started in 2008 and employee set is very diverse age-wise but there’s a huge cohort of people who

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are a little bit older than my kids or in my kids’ age range. And so, I am very much in the flow of knowing what it’s like to be at that stage of life; not from within their shoes but a close observer and carer of this. And so, it really informs me as a leader to think – I don’t think of my – the employees, the team as children; don’t misread this, it’s just – I kinda know what the world’s like right now for this age group, and I know what it was like for my age group and I employ people from my age group too and what we’ve come through. And maybe I have a gap in the middle, you know, maybe I’m not so good with people who are 40 or whatever, but I’ve got a couple of good ends of the barbell covered in terms of what would it be to like work here. What should it be like? And the other thing that informs that, which is kind of [Inaudible 0:14:19] I think, is that I grew up in Detroit, my dad was an auto-worker, a toolmaker; and mom was a home maker, bank teller before that, and there was zero professional role models. Nobody in my family had even been to college and I’ve come to realize that that’s actually a gift because my parents only had one expectation which is basically ‘don’t go to jail’, if you boil it down.

Jerry: Right.

Jules: Carry your weight. But there was more nuance, they were people of high principle and really solid character; and so I had zero professional expectations or you know, nothing that I had to sort of, meet or surpass but I had this really high bar personally that I had to be, you know, self-sufficient, solid citizen whose eulogy would be one I’d be proud of and that informs me of a leader in business quite a bit. I don’t feel that pressure I might feel to match up to something that my mother or father achieved, or my brother, my sister, my aunts or my uncles. It’s none of that for me. But I’ve got his huge, sort of, sense of carrying that character into this business. My parents are both deceased but would they be proud of that? I think there’s – I dated a boy in college who came from a pretty wealthy family and I remember him saying to me, “You working-class people, you are so much happier.” It was kind of offensive but [Crosstalk]

Jerry: But there’s a funny-sweet observation even in its offence. Tell me more about it –

Jules: Yeah.

Jerry: – ‘cause my father was a proofreader and worked for a printing company; for the same printing company that he started working for in high school. My mother did not get a job until the 1970s when my father lost his job, and was unemployed for six years, and had to fold the laundry for the first time in his life and experience that disruption and change. So, I get that working-class background. Tell me, what did it really mean to you?

Jules: You’re not really chasing anything much in that background. There’s a survival element which makes you know, Maslow’s Hierarchy fairly simple for you, but you know, just sort of taking care of your children in everyday life is a success;

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right? You don’t – and you can take your work often as visible, you can take pride in that. It’s not mysterious. Success is not abstract and it’s not conventional, it’s not what, you know, you and I think about when we talk about startups particularly but there was that sort of sense of – on my entire street, I was just talking to somebody about it yesterday that you know, the street full of – you know, those green, Monopoly houses –

Jerry: Yes.

Jules: – they were all separated by the width of a driveway, 20 on each side, there were train-tracks at the end, and a diesel plant beyond the train tracks; I could name every house, every person in there and I believe we would probably have more commonality in our values than what I ultimately probably found in my suburban you know, upper-class, middle-class street. A lot more commonality and there’s kind of a contentment or comfort in that; that is a gift.

Jerry: It sounds like that too really informs your leadership; is that right?

Jules: Yeah. You know, I did go to some pretty rough public schools, and so my most entrepreneurial thing I did was I sent myself to boarding school. I actually kind of snuck behind my parent’s back and got applied to a school, and ultimately, obviously, they had to get involved and they were supportive to a point. Their point, the limit they would hit was, ‘If you ever become one of those people, or you become too big for your britches, we’re pulling you out of there’. So, when I – I love when I have, say, like an uncle or aunt visit here and I can walk them around introduce them to everybody in my company. I’m proud of both sides. I’m proud of the employees, I’m proud of the family I came from, but I want them to see in the people here, and their response to both me and the company, something they can recognize from that background. Like each person here is known, is valued, is secure in themselves, all those things. So, that doesn’t take a PhD to recognize.

Jerry: Or an MBA.

Jules: Or an MBA, no; you outed me.

Jerry: What do you mean?

Jules: I never lead with that; I don’t tell people I went to Harvard.

Jerry: Yeah well, what I’m hearing is that there is this profound sense of connectedness to – and I’m gonna use a Buddhist term, ‘the ground’ ‘the ground of life’, you know. That is a powerful part of the way you lead and I’m really resonating with the values. I mean, you spoke of your three children, I have three children; one entering college, the other two beyond college now and when I think about some of the things we talk about, I often tell this little story: my daughter, Emma

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graduated last year and began teaching for Teach for America at a charter school in East National. She encountered some very profound poverty really for the first time in her life. She knew it conceptually and she certainly has a consciousness about it, but to deal with children who are hungry every day, was just a different experience for her. And of course, this past summer, Ferguson exploded, and Michael Brown was shot, and I remember her calling me and saying to me, “Dad, you know, how do I prevent my kids from growing up to be Michael brown?” And the words of a good friend of mine, Parker Palmer came to mind and we watched a video of his about standing in the tragic gap between the world that we imagine is possible, and the world that is and how we have to stand in that place. And then later, as the summer progressed, we talked about her experience at her school and she told me a story that her principle, who is a young man himself, had discovered that she likes this green juices, the fresh juices and all this. So she started finding green juices on her desk every morning. And what I often say is, I want to help create companies where people with an open heart, like my daughter has, and a consciousness about the world, are met by leaders who put a green juice on their desk.

Jules: Yeah, that’s really good. That resonates for me.

Jerry: That’s it.

Jules: It’s as simple as that. He doesn’t have to spend any time on it, and he’s not even there physically, but he’s saying, ‘You matter. I know a little bit about you and a little bit about – I’m gonna act on’.

Jerry: Yeah, and I see you as you.

Jules: Yeah.

Jerry: Not as a means to the end –

Jules: Yeah.

Jerry: – but as part of a community of people who kinda gather together with some sort of purpose, in this case, in The Grommet, it’s perhaps citizen commerce, perhaps it’s creating a more beautiful world that your heart knows is possible. Perhaps it’s about you know, as one camper who came to one of our bootcamp said, “The full actualization of everybody who comes to work” and that Maslow hierarchy of needs. That – if you see me being excited right now, it’s because this is the thing that gets my juices flowing. It’s really imagining work not as a dreadful obligation that perhaps your father, the toolmaker or my father the proofreader, or your mother the bank teller, or my mother the homemaker felt. But work is a means to creating something more in ourselves.

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Jules: And by the way, it’s – I mean, your startup audience is always in a battle for survival, a race against time and I think this is a way to help with that; so if you – you can't be this way unless you mean it, so you can't fake it.

Jerry: Right.

Jules: But if you mean it, it’s actually really great way to make sure you have the best team. It’s kinda simple but we can always recruit the best people – we’re in Boston and we can always recruit the best people. This kind of – the company’s done well, so it’s not independent of the company but the reputation we have for the community or the environment we’ve created – I have this thing that I translated to the whole team: when we were only ten people, we were about that size for a long time for years, and it was real survival mode. It was tough times, it was when the economy collapsed, capital was hard to get and we were not getting it. And so we did the work of about 40 people with 10 people and how do you get people to do that for four years? There is some cycling in and out, people did fatigue but, people were mainly steady and one of the things that I did was, okay, I can't pay these people what they deserve, I can't give them visible promotional opportunities, I can't even make this company famous so the resume is great, you know, it’s a lot of can't-do, but what can I do? I gave them great work and stretched them beyond things they get in other companies but then I would do kind of this softer side of things which is, I pretty spent a big part of my weekend thinking, okay, if I showed up in the morning and there were flowers outside the door, or it was somebody’s birthday and it was recognized, or there was a speaker coming in on Wednesday who was gonna talk about something pretty cool, you’ve mentioned conscious capitalism, I think in so many words. We had the man who wrote that book come in – those kind of things like, if I had a special guest, they never let them not talk to the whole team; they had to talk not just to me. I would do all these things that really didn’t – they cost time, not a lot of money, a big part of my weekend and then when the company started growing, that wasn’t scalable for me literally buy the snacks for every single person and know what they liked and all that. So I created this structure that I call kind of like – it’s like a vaccination against growth or for growth I guess; I want everybody in the company to hold a piece of our culture that we agree matters. It’s more behaviors; our behaviors. So, everybody is a VP of something, no matter what your job is, you have a second job. VP of something, I'm VP of garden. Like we moved to a space – you mentioned being grounded, it’s a ground floor, old factory building and it had a strip of weeds along the sidewalk and I hated that when we were moving in. So, I put in a garden, a very little urban garden, but that’s my VP job. I maintain that garden and other people have welcoming new employees, other people have lunch and learns, other people – I have a VP of carpets, believe it or not. A ground floor office, the carpets in Boston get crummy. So I think it’s a little like a New York subway, if the carpets are deteriorating, other things start to get neglected. So, we each own a piece, that’s a kitchen [Inaudible 0:26:57] that’s a crummy job so we only do that for a month. But the point is, and I’m very overt with this, we don’t do jobs we don’t think are important. You know, like we

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change jobs if they start to become obsolete but we don’t have an HR – we have 55 people; we don’t have any HR or any Office Manager and it’s really inefficient not to have those two things. Eventually we will, I value those functions but right now, we’re holding on to ‘No, we’re all this’ and we’re all maintaining a piece of this culture, this behavior, this way of being, so that when we go from 55 to 100 to 200, you’ll know when somebody is not really behaving the way we kind of want it to be, because you held that job, or you created that job, or you watched someone else do it. And that’s kind of my – the only thing I can think of to sort of inoculate the company to hang on to those things is to distribute the responsibility.

Jerry: I am so impressed.

Jules: Thank you.

Jerry: I mean, it is beautiful. It is – you know, and we live in a culture that lionizes a kind of – what I believe, there’s a kind of false aggression that’s actually a cover for fear.

Jules: Yeah.

Jerry: And what I’m hearing is, you know, an incredibly strong leader who I have to imagine, dealt with her fears especially when the economy collapsed and rather than covering those fears with aggression, reached in and found what I think is the most powerful leadership tool available: love, faith, care, culture and invested in those things. And going back to our first conversation about success, from my lips to God’s ears, The Grommet grows and expands and sustains itself but if that doesn’t come true, I can almost guarantee that the people who have worked with you, ‘cause I won't even say ‘for you’, with you, can walk away knowing that they had one heck of a ride.

Jules: Thank you.

Jerry: So, you know, the audio of this is the only thing there, but I will give you a deep bow, and that’s a tradition that we do at Naropa but it’s –

Jules: Thank you, that’s special.

Jerry: Yeah. It’s powerful. So let me go back to that for a moment if we may; was I right in saying that you had to confront your fears in order to do what you’re talking about, to reach into your strengths? I imagine there were times when it was scary, 2008-2009?

Jules: I was never not-scary for a long time. It’s still not – I think anxiety is a big part of this role, you know, founding a company anyway, so, I get more nervous when I’m not anxious and I am, badly enough. And that’s a little bit of a learnt habit

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from my childhood as well – I'm sorry, I keep going back to that but I know it matters.

Jerry: It’s what I do.

Jules: Yeah, I know, you have super powers, I hear. But, I learnt like when I had to go the – and went – I told you, I went to boarding school and it was a shocking experience, that was the most scary thing I had ever done. Every day I was nauseous and had to show up in a class like say, Algebra-2 when I never had Algebra-1. So I survived basically. I learnt – and this is an entrepreneurial trait that anybody can look in their own life and find like, ‘Okay, when did you do that thing that was harder than the thing you could have done and you prevailed or at least survived? And you kind of like, you built up this internal bank account of confidence in yourself.’ So I was building that bank account up from a really young age and I had learnt this habit of seeking the scary experiences. Not risk-taking for risk-taking sake but you know, knowing I would grow or the fear would not be a reason not to do something at least, you know, that was just part of the texture of an experience. It wasn’t the focal point, it shouldn’t be the focal point for me. But if it was absent, then I would worry a little bit that I wasn’t pushing myself [Crosstalk]

Jerry: You were on that growth edge.

Jules: Right. But what was hard about this one, you know, each one has different fears, different things I’m facing. Being a parent is scary too, that was different fears –

Jerry: All right, I think it’s one of the most profound fears I’ve ever had. All right, go ahead, I’m sorry.

Jules: Oh, not that it matters too much.

Jerry: Yeah.

Jules: Anyway, but this one, what was scary was that I didn’t see the economy, the crash coming and our business had two big problems then. One was the capital markets were closed for the most part and particularly closed to me on two counts; one was the business itself was – there it is, a very happy and optimistic business, we launch products, you know, the things coming out of kick-starter and [Inaudible 0:32:57] that need to go from you know, ‘nobody knows you’ to a business, and makers and it’s such a positive business. And these times were so, you know, doomsday and everybody just wanted us to be Groupon, or a daily-deal site, or just didn’t believe that there would be new products and that people would care about the future ever again. You remember, it was profoundly scary, negative, pervasive, everywhere.

Jerry: Yeah.

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Jules: And here we are like, no, people are creating things and they are wonderful and somebody will buy then someday again. This will happen again, it will happen today even, we’re gonna launch one today and that was really out of sync. We were so contrary and not deliberately. It just happened to us that we were contrarian; that made it hard to fund the business. We were way ahead of our time basically and out of sync and then when the capital markets closed, being a first-time founder, I worked in two startups, but I didn’t found one and it looked like a typical pattern recognition founder. And what I was describing, I'm sure I didn’t do the absolutely perfect job was complex and white-space. I mean, I’m a designer and I can see the future quite often, I have to. That’s what I was paid to do. Nobody designs a ‘today’ when you’re an industrial designer. So it’s just a discipline for me to see where behaviors and technologies intersect to create opportunity. It used to be products, now I do it for businesses and that skill set was not something I could create credibility for, that people did not believe I had that. And I felt that was probably because I didn’t look like you know, the person that they think does have that skill set.

Jerry: And what do you mean?

Jules: Age and gender, primarily.

Jerry: Age?

Jules: Of course, I look like a housewife from Darien, Connecticut. You know, like, ‘Is that the person on Silicon Valley?’ right?

Jerry: Right.

Jules: ‘Is that the lead protagonist company founder?’ ‘Will that ever be? Never.’

Jerry: Right so, you were the wrong age, the wrong gender –

Jules: The wrong hair color.

Jerry: The wrong hair color – for our listeners, your hair –

Jules: I’m blonde.

Jerry: She’s blonde, right and so there’s the Darien, Connecticut look.

Jules: Yeah, I got braces for a long – when I was 29 my teeth looked like those waspy teeth.

Jerry: Right.

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Jules: They don’t know like [Crosstalk]

Jerry: I was gonna say, I’m a Brooklyn thing; so, they don’t know the Detroit-Brooklyn-Oakland you know, connection.

Jules: Yeah. And I didn’t know to claim it in a way I would now.

Jerry: Tell me more about that because I think there’s an opportunity here, not just as you know, as three-time startup person, as clearly an experienced and thoughtful and purpose-connected leader, there is an opportunity here. I’m gonna call forth the leader in you even more so; what do you mean, you didn’t know that you should claim it?

Jules: Well, beginning a business and building a business, whether it’s recruiting team members, or investors or customers, they are – the things I used to make fun of the sports and military analogies are actually true for these endeavors. There is a sense of a battle and a competition that you are going to face, and no one is going to hand it to you. You’re gonna work really hard and fight for every inch of land you grab and even with the things we talked about, the sort of purpose-driven leadership, still fighting hard even to those things ‘cause you’re doing them on top of all the normal things, right?

Jerry: Right.

Jules: You know, it’s a new layer. So, the grit that I developed in my background, you know, growing up in a tough neighborhood and you know, bouncing myself out of there at 14 and even further back. I was the first girl in Detroit Public Schools to wear pants to school. I mean, I’m ageing myself but we weren’t allowed to wear pants and it was freezing cold there. One day, I just had had it; came home at lunch, changed and next day a teacher wore pants and it was over. The whole policy changed. I don’t even know why, or how. So I was kind of used to like sort of saying, ‘This doesn’t make sense’, ‘This isn’t right’, ‘I don’t accept this’. This is not how I want my life to be. I don’t want to be a bank teller. I read a lot of books when I was a kid and got a lot of big ideas about what one person could do and so, it’s as core to me as anything; the sense of ‘You can't tell me no’ or ‘You can't tell me that has to be done that way’ because every single thing I did from the time I was really young, was carving a new path. I would not have gotten anywhere if I accepted what was expected of me.

Jerry: So what I’m hearing you do, and correct me if I'm not hearing it correctly. What I just heard you do is claim the totality of who you are; your gender, your experiences, being the first girl in Detroit schools to wear pants, the strength, the wit, the grit, the totality of you and claim that rather than necessarily play it by – what one camper once said to me, is the ‘startup playbook’ ‘cause I don’t fit the image of what a VC was; I didn’t go to Harvard, I didn’t get an MBA.

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Jules: Yeah, good point. Such a club, that [Crosstalk] 25% of VCs. What profession is dominated by one little school? That’s amazing to me.

Jerry: Right, and insane. I have a completely, you know, strange background. I don’t fit the mould either and I think we’ve got two people reaching across Skype, connecting with a whole notion of claim the wholeness of who you are and step into that as a leader. Does that resonate with you?

Jules: Yeah. The most recent pitch I did for investment, I said to the person, “Look, I have plenty of credentials but you can go on LinkedIn and read all those. Let me tell you who I am.” That’s what forms this work, and this project, and this company and what I do. That’s much more important. That’s why honestly, that’s why young founders can do really well too because it isn’t only experience; it’s who you are too. I happen to have both –

Jerry: Yes.

Jules: – you know, I have a very full playbook at this point but you know, I would – that idea of being the person who sees something and can push through, can happen at any age.

Jerry: Yeah, or any gender, or any race, or any sexual identification –

Jules: Yeah.

Jerry: – or any orientation that it’s really not limited to somebody else’s view of what an entrepreneur is.

Jules: Yeah, but here you were in PE, and you had to be the same as anyone else, at least as a group, the partnership to recognize the patterns of success and reproduce history; I mean, that was the safest thing to do.

Jerry: Yeah, I used to joke, I wasn’t very comfortable wearing khakis and blue, button-down shirts and –

Jules: Really?

Jerry: – that’s what they were. I remember making my decision to leave JP Morgan which was the firm that I was at after Fred Wilson and I had founded and launched and lead Flatiron Partners. And I remember talking to one of my colleagues and a partner, and I said, “I just don’t feel comfortable here.” As we were talking before, we started recording, I was young with my depression, this is 2002, I was 38, I was dealing with the beginnings of what was a profound mid-life shift for me. And he said, “I really regret this because Jerry, you know what you are? You are very comfortable throwing a brick through glass windows and we got too many people here as investors, who are a little too uncomfortable.”

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That was a violent image but I know what he was talking about which was, ‘I don’t mind going against the grain’, in fact, that’s something I claim. I was a New York Yankees fan in a neighborhood filled with New York Mets fans ‘cause I kinda liked it you know?

Jules: Mm-hmm.

Jerry: And that’s kinda how I defined myself in that way. So that’s part of my heritage, and that’s part of my lineage and I agree with you, I think you and I – I imagine we’re similarly aged, we get to look back and to know something that many of the clients I work with, who might be in their twenties or early thirties, haven’t yet experienced. Those things that we’re so scared of, they are not gonna knock us down for ever.

Jules: Yeah.

Jerry: They’re not. And if we respond to them with grace, and openness, and heart and remembering our core purpose, we can grow.

Jules: Yeah.

Jerry: Well Jules, I can't thank you enough. This has been just a delightful experience and you know, I rarely say something that I’m gonna say now but talking with you, makes me wish again that I was a VC –

Jules: Really?

Jerry: – because I’d put money into this company in a heartbeat –

Jules: Thank you.

Jerry: – based on its leadership alone; based on its leadership.

Jules: That’s really nice of you to say that. It means a lot, thank you.

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]

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“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 0:45:02][End of transcript]

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#18 The Reboot Podcast - Claim Who You Are As a Leader