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Wanting It All, or Nothing at All: A Case for Being 'Married to your Work'
Full transcript of Founder's Mindset episode ft. Ray & Rebecca Girn
In last week’s episode of the Founder’s Mindset podcast, I got to interview 2 of my dearest friends, Ray and Rebecca Girn, about their experience as married founding members of Higher Ground Education—a company to which I, too, have married my fate in more ways than one.
As case-in-point, here are Ray and Rebecca marrying me off to another founding member of their company, Matt Bateman, with whom I’ve since had a child who attends one of Higher Ground’s schools right alongside Ray and Rebecca’s own 3 children (as our forthcoming second child is also set to do):
So yeah: this conversation felt as personal as it was professional. More than that, it called into question whether there even is—or ought to be—any meaningful distinction between the two.
Listen to the full episode on any of these podcast platforms:
…or just read the transcript below. By popular demand, and because there’s no part I’d want to cut, I’ve reproduced it here in full.
Ray: …when you get the pat on the back is the second you don't need it anymore. You’re not going to get it when you needed.
Rebecca: Life is growth; life is always the next thing that you’re doing or creating…
Ray: …I think life is best when it’s all or nothing. And I’d rather have nothing and have a chance of having it all, and end up with nothing, than to have some halfway version.
Alice: Welcome to the Founder’s Mindset, the podcast where we deep dive into the psychology of founding a company - through the personal stories of the founders themselves.
I’m Alice Bentinck, co-founder of Entrepreneur First, where we invest in individuals to help them find a great co-founder and develop their ideas into a successful startup.
I’m joined by Dr. Gena Gorlin, a clinical psychologist and clinical professor at the University of Texas at Austin who’s been collaborating with us to better understand and support the psychological needs of early-stage founders. Together we will be deconstructing the psychological journey of our guests as they build their companies.
Gena: Hi, Alice. In this very special episode I spoke with Ray and Rebecca Girn, who’ve been close friends (and I daresay personal heroes) of mine for almost twenty years. They’re part of the founding team of Higher Ground Education, where they’re very intentionally building a platform centered around parenting and education for human flourishing. Higher Ground owns and operates more than 100 Montessori schools, including the one my daughter attends in Austin—right alongside Ray & Rebecca’s own 3 boys. Higher Ground also offers homeschool, microschool and virtual school programs, and is helping countless people bring a radically different kind of education to their neighborhoods. And that same radicalism animates Ray & Rebecca’s own approach to life, which utterly defies all conventional wisdom about maintaining work-life balance or not putting all your eggs in 1 basket.
Here’s our conversation about what it’s like to put all your eggs in 1 basket—to live life “all in,” as I’ve heard them describe it. They don’t mince words about what makes it really hard—but nor about what makes it so sublimely and unquestionably worth it.
INTERVIEW SEGMENT 1:
Gena: So, it's a pleasure to have you both, why don't we dive in and just start with some reflection on how the two of you started working together. I know you started not as founders per se. You started working together for a company called Laport, but that in itself was a complicated decision. So, can you just walk us through how you made that decision? What was hard, and how did you think through it?
Rebecca: Sure. Ray was already working at LePort. He started as a teacher, a curriculum developer in math and science, and Ray and I met when we were pretty young, was 20, he was 25. I went to law school and became an attorney. And had romantic expectations of that job, which I think didn't pan out in practice. Not because I didn't love the work, I do love being an attorney and I love legal work, but because I didn't love the culture at the law firm where at least the law firm where I got my job, which I won't name, because there's no point. But, people were angry and insecure and that made for just not a fun collaboration in the environment. And then there was also this element of, I felt like I was murdering my objectivity by being there, which is a little bit of a traumatic way to put it.
Rebecca: But, I did have this feeling I wanted to think in terms of, "What do I think is right, or what do I think is true?" And there is a way in which certain types of law can threaten that type of thinking, because the questions you're habitually asking yourself are questions like, "How can I win or what argument can I contrive?" And it can become an unhealthy mental habit. And so, I had a desire to go somewhere where I could build something, and protect things that were good, and fight for things that were good, and create and grow. And here's Ray over here with this vision to totally transform education, which he had not yet done at that time, but I believed that he was going to. And so, I left my law firm job, took a third of the salary that I had been making, walked away from my bonus and joined Ray, and never looked back.
Ray: I think it was interesting just how many people—in terms of our circle of friends and advisors—how many people objected, or at least had concerns and really warned us about the risks. And, I think, they were right to do so, because, as we'll talk about it, I don't think it was easy, but we saw the upside, I think right from the outset. And so, your risks are always relative to certain upside. And we took seriously those risks. So, we talked through what happens if we get divorced, what happens if we don't get along? What happens if someone's afraid to criticize you because I'm the CEO, or you're not open with me? We just went through all these different scenarios and talked through what it would look like and did our best to prepare. So, we took them seriously. But, for us, it was about the opportunity to do the work together.
Ray: And we are not calm, deliberate people that are well suited for this arrangement. We're volatile, we're fiercely passionate, we argue a lot. But, one, we cared really deeply about the work. And I think it's very important that Rebecca grew up in Montessori education. Her mom ran Montessori school. She in a sense, knew as much or more than I did about the work that I was doing. And there was a level of respect and she was already advising. And I think we were kind of fundamentally on the premise of self-improvement, of growth, of vulnerability as cultural currency, which subsequently has been a feature of the organizations that we've worked at and run. And so, we had what we needed to work through everything, but it took some adjusting, because everything got wrapped up into one.
Co-host commentary on segment 1:
Alice: So Ray and Rebecca are friends of yours, Gena. Tell us a little bit about how you know them.
Gena: Yeah, we go way back. It's funny, the way that our relationship fits the pattern of the kinds of relationships and the kind of life that they were describing, because we too are tightly enmeshed. I am married to one of the 13 original co-founders of Higher Ground, and I've followed their collective story for quite some time. I'm now actually doing some consulting for their teacher training institute. I have a daughter enrolled in one of their schools. So in more ways than one, their success or failure is my success or failure. So I too am part of this tight-knit circle of colleagues, friends, trying to build something great together.
Alice: That's amazing. One of the things that Ray said that I really liked was this idea of, everyone else was talking about the downsides but they would think about the upside. I think that's so, so common when we see founders taking that plunge, their friends and family list the 100 reasons it won't work. The reason why it will ruin their marriage, the reason why they'll never see their kids, the reason why they'll be penniless. But actually founders, and we see this time and time again at EF, the founders that are focusing on what it could be and what the upside looks like, are actually much more likely to succeed. That they're planning to succeed rather than planning to fail.
Gena: Yeah, absolutely. I mean, I think it's notable that they weren't blind to the risks and the downsides. In fact, they talked through them vigilantly. They laid everything out on the table. What if we get divorced? Because you never know, that could happen. What if one of us has to be fired? How are we going to manage that? What are the costs? All of which was just grist for the mill for them, of figuring out how they were going to live this mission that lit up so brightly for them as the thing worth doing with their lives.
INTERVIEW SEGMENT 2:
Rebecca: I wouldn't say that it's the easy path. So, I think if people think, "Oh boy, it sure would be nice to work with my husband, or my best friend." It's harder. It's harder to work with people that you have a close personal relationship with. And it requires more of you in terms of really focusing on facts and being charitable to the other person. And the cost of not working through a disagreement is very high. And so, you have to take those disagreements seriously and work through them. But, the flip side of that is that the reward is way higher.
Ray: And part of the reward is just the opportunity for self growth. And look, I remember many instances where I wanted to be the CEO and table thump and be an asshole. And even though I was surrounded by people who were not afraid to speak to me, there was some way in which having Rebecca there, she just wouldn't have tolerated it. And I had to be my best self. I had to. And it wasn't fair, because I'm bearing this on my shoulders and I should get to be an asshole, but I can't because the context demands that total view of who I am, and it was great. I think it forced me to be a better person. I also think that the very core to who we both are, is the integrated life, is a life in which you're one in which you're the same person at home, and at work, and with your friends. And I think that we've had the fortune of living that life.
Co-host commentary on segment 2:
Alice: The idea that Rebecca mentions about the cost of not working through a disagreement is really, really high. But normally you can go home to your spouse or partner about it, rather than actually addressing it. I think there's something about that intensity of their relationship that they have, both through the work and through their personal relationship, that means that they are making very intentional decisions about managing that relationship, that I think a lot of other founders can learn from.
Gena: Yeah, absolutely. I think it's really inspiring how they keep each other honest. A big part of their management of this integrated life—the fact that they're married and that their kids are also customers of the school and that everything is connected, it keeps them honest. Like Ray mentions, it forces him to be his best self. We all need to be able to hold ourselves accountable in these ways. They have found a way to do that, partly through their marriage and through their personal life.
INTERVIEW SEGMENT 3:
Rebecca: Just last night, Ray and I were discussing just tactics for having conversations where we both get what we want. And we decided on this approach where we're going to have this running agenda, where anytime that we have a little bit of time to talk, we're going to pick stuff off the agenda so that we're not like, "Because I want to share things, but Ray wants to talk about things." And so, we have this tactic that we're going to try. And Ray said, "Should we put work stuff or personal stuff on the agenda?" And I said, "We have to put both." There's no universe in which our conversations don't move fluidly between those two things. So it's the opposite of that Chinese wall division between ‘turn off your work brain and turn on your home brain.’ We quite explicitly reject that, and we want to be integrated people, and to make connections between work and personal, because there are so many to be made. And there's so much learning that comes in both directions.
Ray: Another couple points that are relevant here is we have pretty clearly defined and differentiated domains. And so, we do work together as part of a broader founding team, not the same organization, but we're not doing the same thing collaboratively we do together all day. There's a lot of trust and space. And then we circle back and come together. And then I think that in terms of our personal life, part of what you get is no diversification of stress. So, everything kind of hitting at once. And so, at home as well, we've had the experience of both doing everything. Rebecca's traveling, I'm doing everything. I'm traveling, she's doing everything. We're navigating whose priority is bigger and who's going to watch the kids, even though we work in the same organization. So, I can be like, "You know what? You got to get that legal agreement done. And I can push off my thing till tomorrow," or vice versa. So, it's required both coordination and some kind of meaningful separation of terms of scope.
Gena: I know I've also heard both of you speak of how differently you manage stress. And so, I wonder if you can bring us into some of that challenge. When things get really stressful. And let's say when the big calamities happen or are just around the bend, how do the two of you cope with that separately and together?
Rebecca: So Ray, one of the things that makes him a good leader is that he romanticizes the situations that he's in, and he makes it part of his story. And so, if we're going through a very hard time, Ray does this inner work where he integrates that into the romantic story of what he's doing, and why he's doing it, and how it's inevitable and a chapter in the book. And I need to mourn things when I lose things, and I need to vent. And so, sometimes those two things can, unless we understand what's going on and sort of navigate it, they can fight a little bit, because my need to vent can drag down on Ray's very effective strategy of romanticizing.
Rebecca: And I think you've got to be able to do this as the CEO. You know why, because you can't vent to anybody. There is nobody in the world that you can vent to. And everybody dumps their stuff on you and you have to take it in and filter it, and process it, and turn it into decisions, and action, and evaluations. And so, my stress management techniques would not work in a CEO role. But, then there's still that marital dynamic of, "Okay, then who do I vent to? This is a need that I have."
Gena: And so, while on the subject of losses and tough transitions that you Rebecca needed to process and vent about, and Ray, you just digested them as part of your narrative. Maybe you can both talk a little bit about the big transition that you made from your first company that you didn't own, but where you both worked to the founding of Higher Ground.
Ray: I grew up at a company I joined in 2003 as a teacher. It was a small set of preschools. And I grew up in a company ultimately becoming the CEO that reflected everything I wanted in terms of the work I wanted to do and the mission. And I hired a leadership team. We all grew up together from our mid twenties into our mid thirties, and we're quite successful. There was friction and I was bumping heads with the controlling owner and just some differences in vision.
Ray: And it ended up leading to dramatic separation that was hard on everyone involved. I really needed to frame it as Rebecca was saying, as part of the story, as like, "This is life. If you want to pursue something great, you're going to get punches out of left field and you can't become cynical, and you can't stop making handshake deals. And you can't let it change the way you approach. This is to be expected." Of course, right? Of course, anything good is hard. And I was really clinging to that view, I believed it, it wasn't just an illusion, but it was work.
Gena: Didn't you take your kid to the mall the night before you knew that this calamity was about to take place?
Rebecca: You'll have to let me tell this story. So, this had been building for a while and it was clear it was coming to ahead. We still were hoping against hope that maybe there was something solvable, but we were coming to the view that it was irreconcilable and there would have to be a parting of ways. And we were pretty sure that was going to be a dramatic event of Ray coming into work and getting fired the next day. So, we were expecting that. And what did Ray want to do the night before?
Rebecca: It still is very moving to me. He wanted to go to the mall with our two young children, one of whom was under the age of two and the other of whom was a newborn, two months old. And he wanted to ride up and down the escalators with our toddler. And it was like this joyful lighthearted family experience. That is a moment in my mind that's preserved, on the eve of this really terrible traumatic event that we experienced as something dying that we cared very much about. And I think that really speaks to what we're talking about in terms of dealing with stress and making it part of your story.
Ray: The other thing I was going to say is that I also felt like, again, we're a unique situation because it's not just me and Rebecca. There's a group of a dozen people who kind of grew up together at the time. And I felt like everyone was brought into the loop and something that I felt I had been in since carrying was now. I had my avenging angels, and I had people defending me, and understanding. And I think what I was not able to do effectively was just sympathize with how hard it was.
Ray: And I'm not saying this is a kind of virtue, but I needed to insist that it was fine, and it was easy, and it was okay. And part of me, again, deeply believed that. And part of me was just scared of acknowledging that it was hard. But, I think, it was very alienating to people who I think cared as deeply as I did and needed to experience the loss. And so, there was a way in which we weren't able fully to connect, I think. Obviously I have in retrospect understood it, but we just needed something different. I think it became a source of learning, but it was, as Rebecca put it, nothing had died, so I am not mourning. That was my attitude.
Rebecca: And there's no need to put it in terms of something irreconcilable because the fact is that both are possible, and this is why 12 people left and followed Ray. Maybe not just this, also the substantive specific vision of education, and a number of other things. But, this is this quality of making things into a grand story and taking that perspective on your life is... I want that in my life, especially since I sometimes get in my own way to bring it to myself.
Co-host commentary on segment 3:
Alice: They talk a little bit about how they manage stress and the differences in that. I mean, at Entrepreneur First, the co-founding teams that we make could not be more different to this because we take strangers and help them build that relationship. But there's definitely this similarity of, whether you're very close and great friends or in a relationship or whether you've just met each other, there will always be situations where your styles of stress management, of how you work or communicate, will be at odds with each other. How do you help founders think about this and manage this?
Gena: I mean, I think the fact that Ray and Rebecca can never fully unplug or get away, both from each other and from their stresses. I think it just lays bare that universal challenge you're talking about that all co-founders face, which is that they have to be able to work through challenges together, while managing their differences. So for Ray and Rebecca, there's a way in which his ability to immediately digest whatever stressor, whatever setback, whatever failure into this romantic narrative, it's what allows him to cope quickly and to stay on mission. At the same time, it makes Rebecca feel really invisible, at least in the moment when she just needs time to grieve. At the same time, as you hear them talk through how they've managed this difference with the years, I think it's made Ray more empathetic. I think it's made him recognize in certain ways, not just what Rebecca needs but what other team members need from him. What in some cases their children need from both of them. Their children may need some empathy about this tantrum that they're having, even though for Ray and Rebecca it's like, okay, this is not going to matter in five minutes. But it matters right now to you, and we need to take that seriously.
Gena: So it's actually helped Ray to address a blind spot and I think become a better CEO, a better dad. And for Rebecca, I think she's actually internalized not all, but a lot of that romanticizing strategy and ability. I think the fact that she can see it and be inspired by it in Ray, actually gets her through the grief, while not eliminating her need to have friends she can go to who can actually listen and who can empathize more readily, and who can cry about it with her. I think that's true for any co-founders, married or not, that they can't just be each other's sole sources of visibility and social support.
Alice: We see this around conflict as well, different individuals having very different conflict preferences. I remember working with a team where they were really struggling around one particular thing.
Alice: And when they did Facet Five, what they saw was that one of them thought conflict was productive and useful and energizing, and the other found conflict stressful and demoralizing and draining. Once they knew that, they could modify their styles to accommodate each other. But it was just knowing that, that was so important. So just having that conversation and observing how each other is behaving, can be a really, really useful foundational point for teams.
Gena: I think going even further in terms of what they need to come to understand about each other and about their respective preferences, is that these aren't just completely neutral preferences in the sense that, have conflicts or avoid conflicts. It's all the same. You're not better off. I mean, you need to sometimes have the conflict and there are better and worse, more and less constructive ways to have that conflict. And you're going to experience it very differently and you need to be able to deal with that. But there's an underlying principle there that they do need to align on. I think for Ray and Rebecca, both of them have come to understand better and better with the years what each of them is getting at with their respective coping strategies. And there's something really true and important each of them is getting at, right? We talked about how for Ray, it's not just that he's pulling wool over his eyes. In fact, I think it's the far opposite of that. I think he sees something. He's able to see a really far-reaching, far-ranging vision of his life, of the world that he's helping to build, where he actually can understand how this moment fits within that larger scheme.
Gena: He sees that, well, of course we had to go through this huge hurdle where we have some kind of big confrontation and we get fired, or somehow we have to create some sort of fresh start because we didn't align on the vision, and we were more ambitious than this. Of course, that was going to come to a head. And I think what Rebecca's also bringing to it is, this meant so much to us, this period of time and of our lives, where we learned how to lead and we learned how to help children to learn and grow. We built this thing largely with our bare hands and together and I don't want to just brush it under the rug. I want to really acknowledge what it's meant as part of our life narrative. And Ray might be pretty quick to move past that stage. Okay, well, that's all water under the bridge.
Gena: But I think it's actually really important for both of them to remember what it meant and what they loved about it, because then they draw on that. They draw on what was really wonderful about the previous experience that didn't work out in the end, but that still in many ways formed the blueprint of their next project. So there's a truth that's being captured by both of their approaches and by really thinking through, okay, why do we react in these different ways? What is each of us needing and what is each of us getting at here? I think both of them are able to see a fuller picture than either of them would alone.
INTERVIEW SEGMENT 4:
Gena: Yeah. So, listeners hearing you speak of this grand romantic story that you, Ray, were able to weave this tragedy into. They might think, "Oh yes, this is a convenient lie that Ray was telling himself." But, I think, what happened next, I think, really attests to the credibility of that story. And if we look from the night before the big calamity and what you chose to do, and what you all chose to do next, maybe you can speak a little bit to how and why you grew from that moment, and what you chose to build.
Ray: Yeah. For me, first and foremost is that I walk and live amongst giants. And we had a group of people that understood that we have this one life to live, let's make the most of it, and let's try to do some great work and jog the world forward a little bit. And, I think, that because we had that view, you're always just one conversation away from rendering petty and insignificant, whatever the kind of obstacle that is in the way. There's a path to get there, because that underlying view is shared, this is the life that we want. And so, we went out and we built a company, and this is a step of life, these great moral choices. And I think what unites us all as a group is we don't want a life that doesn't involve that. And we can always come back to that. There's that foundation. Our core value or one of our core values at Higher Ground is, "Mission without Martyrdom." That we're not bearing crosses, we're making choices, and always in the end, you can step back and remember, "This is a choice and I don't have to make this choice. Do I want it?" And when we do that, the answer's always, "Yes."
Rebecca: Yeah. So Ray, you might want to say a couple things about where the company is just to make that story a little more concrete for people.
Ray: Sure. So, we're building a platform that launches and operates Montessori schools, or schools [inaudible 00:18:38] Montessori principles, from infant care all the way through adulthood, through high school. And it is a very complicated complex system involving real estate, involving teacher training, involving just school setup and operating technology, learning technology. But in the end, we want to basically serve children in any modality. So, you could be homeschooling, you could be a stay at home parent, you could be at virtual school, or we have 100 now brick and mortar schools across the country and world, and 100 more in the pipeline. There's a lot to say about our actual business, I'm happy to talk about that. But, the bottom line is that it's a mission driven business in the kind of deepest sense of that term. It's also a business where each of us finds our own particular flavor of the work that we want to do in terms of the daily activity that we enjoy.
Gena: So, just connecting some of the dots. Both of you have mentioned in passing, or Rebecca, you mentioned your boys and how they featured at least in one important moment in your lives. But, here you are building an education company, building a company whose mission is to transform the way children grow up, and how the souls and the lives of children are cultivated. And you are parents of three. So, how has that worked?
Rebecca: Yeah, so we have three boys. They all three go to our schools. So, literally all of our eggs are in the same basket. And the integrations between work and family are pretty significant. So, our children keep us honest with the business, because it's a very good gut check to say, "Would I have my children in this classroom?" And if the answer is "No," it's not an acceptable classroom. It's just like, it's a very emotionally integrated metric.
Rebecca: It's not the metric that I use to objectively measure classroom success, but it is a very useful internal guideline for me. And then there's just the integration between management, which is something that Ray and I think a lot about, and push ourselves to get better at. And the component skills of management are very similar to the component skills of parenting in terms of being an active listener, modulating your own emotions and staying calm, figuring out a course of action but not imposing it on somebody else, and bringing somebody along to choose it and see it.
Ray: It's important to me, and I'm proud of the fact that I, and we, are examples of the possibility of living a work centric life and having a family. And I don't really have any guilt or any reservations about knowing that my work is the core of my life. And yet I love my kids more than anything in the world. The two are in sync.
Ray: And, I think, it's the right way to live for me. I also think it's important that our boys are seeing Rebecca live that life, and that they're seeing both of us. We joke sometimes that kids must think Rebecca and I could be divorced, because one of us is always on the road. But, we both do everything. And they see that and they do not experience themselves as the hub around which our lives respond. They experience themselves as part of a family, but understand that a life of work is what we regard as the good life.
Rebecca: That is the example we want to set for them. The number one thing that we hope for our boys is that they have a driving life passion. And so, if we can set that example for them and show them what that looks like, we hope that they'll find that for themselves.
Gena: It feels related to me what you're saying now. And I remember what really stuck with me, Ray. I don't remember if this was the birth of your first or second son, for which you made the Facebook announcement. But, I remember that the words were, "The best gift a father can give a son is to love his mother." And it somehow feels related. Maybe it's just associative, but somehow these things seem to connect.
Ray: As I said in that post, I don't think you can't always give that gift. And I don't think it's true for everyone. And I think there's plenty of other gifts you can give. But to the extent that you can, in terms of my kids, I want them to see what it is to value someone. And I want them to see, and obviously, particularly Rebecca, how much I value her.
Ray: I also want them on the premise that I'm on, that it's who you love and not who loves you that matters in life. That really defines the quality of your life. It's what you love. It's what matters to you. It's what you value. If I step back and think of the role that I see an educator having, of inspiring inquiry, of awakening the best, there's a real way in which I see my role as a parent as similar, I'm not trying to engineer a certain outcome with my kids and make them be to a certain type of person. I'm just trying to give them an example of what it means to live a full life and then let them figure out their own way to do it, and to enjoy that process of watching them do it.
Gena: Yeah. It feels intimately connected to how you approach your work, and your company, and your mission. And you already said a little bit about this in terms of the role of an educator, but even just the whole process by which you chose to found this company, and the ways you make decisions about where and how to grow. It's so much about the love, and it's so much about expressing and manifesting that love. It's not about seeking the love, at least not in any primary way.
Ray: We're counterculture, because we believe that capability is upstream and belonging is downstream. And yes, belonging is important, but it's the sense that you're capable, that you're able to act in the world, that you're able to pursue the things you want, and then to actually achieve them and enjoy the fruits. That's what makes life worth living. And then as part of that, you have good relationships, and you're accepted, and you're validated by others, but you can't seek that as a primary. You have to have that view starting a company. You have to have that view, because when you get the pat on the back is the second you don't need it anymore. You're not going to get it when you need it. And when they do see it, if you let yourself bask in it, they don't get it. You know it's false. And so, you can't actually fully enjoy it.
Rebecca: By that time, you're already onto the next achievement. Life is growth. Life is always the next thing that you're doing or creating. I'm typically unhappy with things that I've created within a week of creating them, and I'm already thinking about what's the next version of this? Or how do you transcend this? So yeah, I just want to kind of second that emotion of it's not useful really to get applause from other people. But, it is useful to get feedback from them, thoughtful, interesting feedback about why something works or doesn't work.
Ray: Yeah. Montessori has this great quote somewhere where she talks about that experience, that gift, that life can give you the achievement, the writing of a book, or having a child, or whatever it is, and something that you do or something that happens to you. And she has, "If in some such moment, someone vested with authority were to hand you a prize or reward. What would you feel?" What you would feel is, "Who are you that stands so far above me that you can give me a prize?" And being a devout Catholic, her next line is, "The prize for such a man in such a moment can only be divine." And what she's getting at, I think, is that the things that really make life worth living, other people can't give you, they're in the doing itself.
Co-host commentary on segment 4:
Alice: They talk a little bit about validation seeking and this is an important point to touch on, because it feels like so much of being a founder is about trying to get that award or recognition, the pat on the back. Because when you're running a company, often no one notices, no one cares what you're doing. It feels like those moments of external valid validation are so important.
Alice: Ray and Rebecca explicitly say, it's not what they're focusing on, not what matters. What matters is the impact. You've talked extensively about validation seeking and how that can change behavior, what are your thoughts on that?
Gena: Yeah. This is another instance where I think Ray and Rebecca are fundamentally aligned on their motivation and on the way in which that motivation is really first personal to them. They don't want the appearance of creating a revolutionary education company. They want to revolutionize education. That is what they want. They want to create a community and a culture and ultimately a world of human beings living their fullest lives and thriving and living wholeheartedly together. And any pat on the back that suggests someone else thinks they're doing that, but that is not their own first personal sighting of, oh, hey, we're actually doing it ... we're actually on the right track, it's like an insult to them.
Gena: What they're a little bit different on is how they need to be able to see that, and what role they play for each other and what role other people play for them in helping them to see that and to carry on. I mean, the mission is very much a human-centric mission. So part of what they need to know is that children are experiencing a better developmental trajectory, and that teachers are more engaged and more passionate and more bought into their work than they would be otherwise. They do need to be able to see that. So the kind of feedback they get from teachers, from students, from stakeholders who are actually being impacted by their work, means the world I think to each of them.
Alice: This is such an important point because no founder goes out to create a mirage of their mission, but it's amazing how many founders end up doing that. You win the awards, you get the TechCrunch article, you get the TechCruch Award. Not that there's anything wrong with TechCrunch. You end up tracking your progress through vanity metrics rather than, am I fundamentally changing my customer's life in the way that I intended? It's a great reminder to early-stage founders that often we see early-stage founders who are like, cool, I've done my customer development, tick, done. Actually you're doing customer development the whole way through the founding journey. You're always speaking to your customers and understanding, am I having the intended impact on my customer that I set out to have? It's amazing how often the answer is no. The founders that know that can change it, but there's a lot of founders out there that just never bother or even think to have that conversation. That true, scary conversation with a customer to see whether they are heading in the right direction.
Alice: One of the themes of the podcast that we talked about before, is this idea of being a missionary or a mercenary and the overlap between the two. This feels like probably the most mission-driven company that we've spoken to. Ray says, it's mission without martyrdom, but ultimately the mission is so core to every decision they make. What are your views on how they're processing this very missionary approach to founding a company?
Gena: Yeah. I mean, in some ways having been friends with them for years, I think I've gotten much of my perspective on what it means to build your life and to be ambitious. I think it's so deeply personal for them and not just because they're married and because their kids go to their own schools and because all of these ... as Rebecca puts it, they are really putting their eggs in this one basket, but they're doing that for a reason. And the reason is that everything they want and everything they love, and everything that makes their lives worth living, is this mission. That's how personal it is for them.
Gena: And everything about the company and everything they do as parents; everything they do as friends; everything they do as colleagues, is about that. So when they say mission without martyrdom, it's not a 'me versus my mission' or my mission versus my life, or my work versus... there's no versus. The mission is the thing and everything connects to it.
INTERVIEW SEGMENT 5:
Rebecca: So, this is now making me want to think in the other direction and be like, "But I don't know, awards and prizes can be pretty meaningful, especially when they're given by a body that you respect."
Gena: Yeah. And I think that's okay. But, I was thinking about it too from the perspective that we have visibility needs that differ, I think, person to person. The two of you were just talking about the different ways you process stress. And I also wonder, Ray, as a CEO, also as someone who's been a friend, and whom I've sort of observed and admired for many years, you probably are on the lowest end of the continuum of maybe anyone I know in that need. Not just for the pat on the back, because yeah, I don't think any of us can really need that and still achieve our goals. But, the visibility, the recognition, the acknowledgement, that I do think we all want and need. And it's a different kind of thing. And we need it in varying degrees. And I wonder if between the two of you, even if that's a kind of salient difference.
Ray: Yeah. What I would say is, and I've said this in a talk to our school leaders, time management used to be what defines a great professional, or a great entrepreneur, in a lot of ways if you go back 30 years, 50 years. And now it's permission to play, it's what you need to be able to do is manage your own energy. And so, I think, you're right, that I'm be over-indexing on my particular needs, but the really important point is, know yourself, know what you need. When do you need the kick in the ass versus when do you need someone to indulge your self-pity? When do you need to stop working and take a break? When do you need to cancel your weekend plans and get to work and just clear your plate? You have to keep something in the tank, that is part of what it means to do... You can't be running on empty. Accepting that as part of your scope is core to being a founder and being an entrepreneur. That is part of the work. And the amount of thinking that you have to do about, "Okay, what does it for me so that I can always, again, have something in the tank?"
Gena: And to connect those, it has to be something real. It has to be something credible and actually connected to the work. And that's why I think the pats on the back, or the empty praise that is not actually founded in understanding, or that's going to go away tomorrow. That probably doesn't do it for most founders or most people doing something really complicated. It's the genuine understanding. And it's the pausing to watch the child tying his shoe and focused on the work in a way that is completely transforming his life. I've seen the videos, I've cried the tears. That's going to fill your tank in a way that empty praise just won't.
Ray: Yeah. For me, for example, also the people that I get to work with. But, it's not the happy hour after work. It's the arguing and the debating, and they're trying to figure out the actual work. I just like working with the people that I work with.
Gena: But, that seems pretty core to the love.
Rebecca: And if you connect that back up, because the theme is, "Oh, we're married and we started coming together," blah blah. If you connect that back up, I think that's another perspective that we have is that we're deepening the relationship through the work, and we have that perspective on each other, but we also have that perspective with every single member of our team to one degree or another. The other members of our founding team, there is an irreplaceable bond from starting this company together, especially in the circumstances in which we started it, and how hard the choice was, and how much it brought us together. That's a serious value that we share and it creates a kind of friendship that's really special. And I think sometimes people discount their work friends as though they're not real friends. And I think that is wrong. If work is a real serious value to you, and it's something you share with somebody else, that is a real friendship and an important relationship.
Gena: Yeah. You don't have to be married to a fellow founder to experience those rewards and that integration, and to have to manage some of the challenges that come with it. [cut here; continued after debrief bit below]
Co-host commentary on segment 5:
Alice: We help people develop ideas from scratch at EF, and often people come to us with a pre-idea or a very early-stage idea. What we push them to do is not fall in love with the problem but to fall in love with the customer group. I think this is a really lovely example of that where Ray and Rebecca really care about children. They really care about making those foundational years within somebody's life and how that can change the rest of their lives. So often when people are trying to come up with an idea, they find a very discrete problem, or even a discrete solution. They think they're going to solve, or they think they're going to build and produce. But actually by falling in love with the customer, when you think about the resilience that gives you over the long term, because you are so committed to supporting and making the life better for that customer, that really is where these amazing mission-driven but also highly resilient founders come from.
Gena: Can I just jump in on that? Because I think it's notable that the customer Ray and Rebecca have fallen in love with is a human being. It's not even just a child because that I think would be more compartmentalized. I've seen a lot of people who approach educational theory and methods this way, where they're thinking about children. But then when they teach a classroom of adults, they're really authoritarian and seem to forget all the core principles that they themselves tout when they're talking to a Montessori teacher or when they're dealing with a three-year-old. For Ray and Rebecca, it's not just about children, it's about human beings. And that includes them and that includes their own kids. And the ways that they connect to the best in every human being, that is their customer.
Gena: It's like, we're serving the human being. We're serving the best in humans.
Alice: You and I, Gena, we are big believers in work/life integration rather than work/life balance, to the extent that I'm breastfeeding my little baby as we do this podcast. These guys, Ray and Rebecca, they are fully, fully integrated to the point where they really have put all their eggs in one basket. How do you help founders think about work/life integration? What should they take from the story of Ray and Rebecca?
Gena: Yeah. I think Ray and Rebecca are an extreme example of really being intentional about every aspect of their lives, and designing their lives according to their own genuine first personal conscious vision and judgment of how they want to live and who they want to be. That's something that I think we all would do well to strive for. How much of your life is on your own terms? How much of it have you designed, and how much is just sort of a default mode where you're just still acting out the habit that you formed 10 years ago, because it's what people around you were doing or it's what people in your family were doing and you've never really thought through how well it's serving you? We all have some things like that, because I think it is the default. I think it's really hard work to decide, okay, you know what? This isn't how I'm going to exercise anymore. I'm going to figure out a better way that serves me and serves my life.
Gena: There are no corners of their life to which they themselves aren't accountable, from this perspective of, is this actually how I want to be doing it? They're stakeholders in each other's parenting, in each other's marriage, in each other's leadership. And that really forces them and I think compels them, inspires them, to keep making choices, to keep on being intentional, to account for: why did they drop the ball on this or that?
Gena: I mean, they're doing so many things and they're accountable, not just to themselves, but to each other all the way down for all of it. I think in fact that's true for every single one of us in the life wheel. Because one way or another the minutes will go by, the time will pass, the resources will get spent and then that's it. We'll be done. So it's not a question of, are you going to have to deal with your husband, wife asking you at dinner whether you got this thing? It's a question of, will you have gotten the things done that you wanted to get done, right? Will you have made the choices that mattered? They've set it up so that it's easier to answer yes than no to those questions. I think that we can all emulate their example.
Alice: Well, as a founder ... and I've definitely found this building EF, you're so busy all the time that it feels like intentionally designing how you spend your time or how you spend your life, it never is top of your to-do list. Whereas actually by doing that, you can unlock so much brilliance both now and in the future that otherwise is very, very hard to access. So much of being a founder is just time allocation, effective time allocation. The amazing thing about being a founder is that it is a choice. It is down to you, but you also have to take accountability for that. It's very hard to be the victim when you're the founder because ultimately you make the choices, you make the decisions and then you've got to live with the outcomes. But I think these two just are living that so deeply, it's incredibly impressive.
Gena: It's also incredibly hard and I don't want to windowdress that aspect of it. I don't think that they are ever trying to windowdress that aspect of it. I think Rebecca and I both broke down in tears together at least twice during the recording of this episode. I don't know how clearly that got across. But we're talking about really intense life-changing problems and decisions and dilemmas that they are not cushioning themselves from. There's no cushion and they feel it all. I think that is the cost. It’s really hard work and it's also, the lows are going to be lower just as the highs are going to be higher, and that is just so profoundly worth it to them.
INTERVIEW SEGMENT 6:
Gena: So, as we approach the end of our conversation. I wonder if there's anything looking more to the future and to the ongoing growth, Rebecca, you put it so beautifully that life is growth, and that you're always looking to the next big challenge, the next milestone. What are some of those upcoming milestones and challenges for the two of you? Especially as you think about indexing on the work, indexing on higher ground education and your ambitions for it, and then thinking about what is the growth that you're going to have to do as people and as a couple in order to grow together.
Rebecca: That's a super interesting question. Something that seems relevant is for us, we're trying to do something that's very big in scope. And when we founded the company, we certainly were not capable at that moment of running the size and complexity of company that we are now currently running. And I have the feeling that we're barely keeping up in our personal growth, because as the company goes to each new stage, a totally different set of skills is required.
Rebecca: And sometimes there are moments on the way. I think for some people they're like, "I don't want that set of skills. I just want to be a serial founder." A lot of people make that choice very legitimately, because it is fun to start a company, and get it off the ground, and birth it into the world. That's a fun stage of the company. But, the thing is that Ray and I care so deeply about achieving the mission. That's what we're here for. That's what we want to do. And so, that requires us to scale ourselves up with the company. And, I think, that is hard, yeah.
Ray: It's hard also when they're surrounded by people that you're very familiar with, because you as an individual may be trying to level up and become something that... You see the person you can become that you aren't today, but all the people around you know you. And in the same way that you have to leave home and leave your parents and become yourself. That can become a challenge, because I'm already convinced of Rebecca, her strengths and weaknesses, and she's already convinced of mine. And if I'm trying to recreate myself, she could get in the way, again, unless we communicate, I'm very explicit, and we're very much on the premise that adults can learn, and adults can grow, and one can recreate oneself at any point.
Gena: What is the way that you've done that or that you're doing that now?
Rebecca: So, say for example, maybe Ray and I are struggling to communicate on some issue, and we're not even sure if we agree or disagree because that's the level of the communication. It's not even clear if there's a point of disagreement. And there's some skill of communicating that we have to develop in order to solve this dilemma, or probably to solve other dilemmas, but it's coming up in this dilemma. And so, we identify what that is. And then we're intellectual committed to developing that skill. But, as everybody knows, skills take time to develop, you don't snap your fingers, it takes practice, and you're like, "Ah, I didn't do it again." And so, that's what it is to kind of build a habit. And so, say Ray is trying to develop some communication skill, but I don't believe it. And I'm like, "He's just going to do this old thing that he always did." And so, I communicate through my body language and through the actual things that I say that I don't believe that he's trying or succeeding. I am preventing him from succeeding. And so, I think, that's what Ray means by if you have to grow tremendously and you have to do that alongside of somebody else who's also growing tremendously. You have to think about the ways in which you might unintentionally hold each other back from doing it.
Ray: A simple example would be, let's say, I think both Rebecca and I are entrepreneurs who lean fairly heavily on our intuition, and our intuitive sense of what is going on, and sizing up a situation. And I often don't care what the quote data says, because I know that this is right, or I know this is wrong. And that stops working after a while. And I want to maybe be a different type of leader, or Rebecca wants to be a different type of leader of the programs department. And that's a multi-year process. And most people wouldn't try to make that level of change. But, let's say we want to, or someone else in the team wants to, it's very easy to just assume that someone else is not going to be able to make that transition. Whereas if you met them fresh, you wouldn't assume that, because you hold them to be a certain type of person, including their strengths, but also the areas where they're not as strong. And so, I agree with the point that you can get in someone's way inadvertently.
Rebecca: Just like you can get in your own way. And you have a reputation with yourself and you have beliefs about yourself. And if you're not willing to believe in yourself and your own ability to grow, this is growth mindset. You hold yourself back in the exact same way.
Ray: I have great ambitions for this company. Great ambitions. I think that my biggest fear is the people that see the $2 billion market cap get in the way of the 10 billion, 20 billion, $50 billion market cap putting in terms of economics. But, really the grand mission rather than the kind of lay up. And it scares the hell out of me in terms of what it takes to lead, because part of what the next phase is going to be looking at all the people from myself, onto everyone else that have built the company, to this stage and saying, "Are you the one to lead us to the next stage?" And I don't want to do that work. And I have to really understand that that is the work that's going to be required. What we have to do in the next six years looks very different than what we did in the last six years.
Ray: And so, it's taken a while to make peace with the fact that this is going to be the work for me over the next couple of years, of really looking at how do you take an outsider perspective of where we are, and what if I should be the Chairman and not the CEO. By the way, I don't believe that I think I should be the CEO for decades. And then Rebecca, and then all of the other leadership, and it feels like a betrayal to even do that work. But, in the end, it's about the missions, about we want to achieve something in the world and we're all aligned. And if it's actually necessary, then it's necessary.
Co-host commentary on segment 6:
Alice: Part of intentionally designing your life and how you spend your time is focusing on personal growth. They have a very objective approach to this, that they talk very openly about, if they're not the right people to run the company at whatever stage, then they shouldn't be doing it. This idea of scaling yourself as a founder is so important. I think it's why lots of people find being a founder is so attractive is, you are constantly learning and your learning curve never stops. But you then also have to be very intentional about how you grow and how you grow in relation to your co-founder. One of the comments that they made was around not holding each other's personal growth back because of your expectations about what the other person can and can't do. I thought that was so clear-sighted.
Gena: This is universal. It is by no means limited to married couples. I've seen this kind of unintentional, self-fulfilling prophecy taking hold and limiting what we're able to do, limiting the rate of our growth, in so many relationships, in so many different contexts. I think we do this to ourselves and we do this to each other where, oh yeah, of course she's going to get snippy with me when I bring up the need to call a few more customers, or whatever. So I'm just going to preemptively get defensive because I'm assuming that that snappiness is going to come. Or I'm just going to try to announce that I've made the decision without running it by you first, because I know if I run it by you, you're just going to be unreasonable. And that's often, in fact, true of every past time that you've tried to bring this thing up or that you've tried to have that conversation. And if you believe in the other person's capacity to grow ... forget believe, if you want to give them their best shot, if you want them to grow, you've got to let them grow.
Gena: Any last thoughts on lessons learned along the way since having founded Higher Ground, since having embarked on this integrated journey together?
Rebecca: This is a point that Ray has made to me that I'm... We steal each other's points a lot. But, I think, the idea that everything is in scope. So, you have a neat little pretty picture. You go in thinking there's going to be challenges, but you have this pretty little picture of what the challenges are going to be. And the challenges typically aren't things that you've anticipated. That's why they're challenging, because you have not anticipated them, or planned for them, or done any thinking about them. COVID is a great really dramatic example. But, there's lots of smaller examples where the actual challenge is culture. That's something that we figured out early at Laport, and that was a founding guiding viewpoint when we started this company, is culture is so important and it's the most important thing, and you achieve everything through the resource of culture.
Rebecca: And people encounter cultural challenges, and they're like, "Why won't people just get the right head space and do the thing?" And it's like, "No. Culture is in scope. Culture is the challenge." And so, there's a lot of stuff like that where you have to say to yourself, "Okay, this is the work I should be doing. This is not the work I'm doing to get to the work that I want to be doing. This is the work I should be doing."
Gena: And want to be doing.
Rebecca: And want to be doing.
Ray: I would make two closing points. Talent is a venture game and not a growth equity game. The relative importance in one's life of really great people, no matter how much you talk about it, you should be on the premise that you're underestimating it. And I have been blessed to be surrounded by great people, just surrounded by great people. And, I think, I live in the world, I want to create for that reason. And, I think, that is in some meaningful way, everyone that starts a company has that opportunity, even if it's two people or three people. You're just in this world of trying to solve a problem together. And that is something to be cherished, and appreciated, and protected, and perpetuated. And then I think the second takeaway from me when I look at, especially Rebecca and I working together, is I think life is best when it's all or nothing. And I'd rather have nothing and have a chance of having it all, and end up nothing, than to have some halfway version. And I don't know if that's true for everyone, but it's true for a subset of people, and probably your audience is amongst that subset. And it's easy to say in retrospect, not that we've succeeded in we're in retrospect, we're in the middle of it. I've found it not that difficult to come back to in the moment, and in the thick of it, and in the busy to and fro. I just pause on it, "What type of life do I want?" If you just ask yourself that question, you can often [inaudible 00:43:26] yourself, and I want the life where I have it all. I have family, I have a marriage, I have kids that I love, and I have this kind of work tying it all together, that is at the core of who I am.
Alice: Thank you for joining us on this episode of the Founder’s Mindset. Make sure to subscribe or follow us to be the first to get every new episode. And if you enjoyed the show, why not leave us a rating or review to help us reach even more people? We would hugely appreciate it. As always, you can learn more about Entrepreneur First by heading to joinef.com. I’ve been Alice Bentinck…
Gena: And I’m Gena Gorlin. See you next time!
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