In this thought-provoking episode, Jaclyn talks with James Rhee, a teacher, national best-selling author, and Investor/CEO about kindness within private equity, his novel 'Red Helicopter,' and how kindness has shaped his personal and professional life.
James Rhee joins Jaclyn this week for an informative and intriguing discussion about his life, his novel 'red helicopter', and how kindness can shape the professional world.
James Rhee is a high school teacher and Harvard Law graduate who became a private equity investor and unexpected CEO. He bridges math with emotions by marrying capital with purpose. His transformational leadership has been recognized by the leading business and civic organizations. His national bestselling book, entitled red helicopter―a parable for our times: lead change with kindness (plus a little math), was published in April 2024 in partnership with Harper One, an imprint of HarperCollins that seeks multi-platform ideas that “transform, inspire, change lives, and influence cultural discussions.” He is working on related film, music, and television projects. His TED Talk and Dare to Lead interview with Brené Brown have captured the imagination of millions.
red helicopter, his media-education platform of the same name, is an operating system—a way—, that creates, measures, and amplifies a sustainable balance of life, money, and joy in the life of business and the business of life. Its systematic impact has been informed by, successfully applied to, and further refined by decades of investing, leading, and teaching at the highest levels in a myriad of environments. red helicopter’s methodologies are grounded in the realities of history and policy, as well as the truths of finance, behavioral psychology, and cognitive science.
This podcast is one of the many ways we live out our organization's mission to educate and inspire people to choose kindness. Visit our site kindness.org and sign up to become a part of our global community which spans more than 100 countries. It's free to join and when you do you'll be the first to get access to our latest research, tools, and even episodes of this podcast. Let's build a kinder world, together. Contact us at podcast@kindness.org or on social at @kindnessorg.
Important links from this week's episode:
kindness.org
redhelicopter.com
Follow James
IG: @iamjamesrhee
X: @iamjamesrhee
Linkedin: jamescharlesrhee
Follow Red Helicopter
IG: @theredhelicopter
FB: @theredhelicopter
Linkedin: the-red-helicopter
TikTok: @theredhelicopter
Credits
Host: Jaclyn Lindsey
Guest: James Rhee
Producer: Melissa Malone
Music Composition: Chris Christiana
Design: Ben Gibson, Christine Do
Transcript of this episode can be found here: whykindness.simplecast.com/episodes/james-rhee/transcript
James Rhee- Why Kindness Transcript
Intro: Why kindness? Because it makes a difference. For connection. Kindness can change lives. It's contagious. The science says you'll be glad you did. Kindness is powerful. It’s the key to a healthier, happier world.
Jaclyn: Why kindness? While no one answer is the same, one thing is clear. Kindness is something we all know, but do we know why it matters?
I'm your host, Jaclyn Lindsay, co founder, CEO of kindness. org. And you're listening. To why kindness?
Hello friends. We are back with another episode of why kindness. I'm really honored and excited to welcome our guest today. James Rhee is a former high school teacher and Harvard law school graduate who became a private equity investor and unexpectedly an acclaimed CEO. He bridges math with emotions by marrying capital with purpose while composing systems that bridge people's disciplines and ideas.
His transformational leadership has been recognized by leading civic and business organizations, and he is the author of the newly released Red Helicopter, an incredible book that brings kindness to life in leadership. Anyone who puts kindness on the cover of a book is someone I want to talk to. I'm really thrilled to welcome James Rhee to the Why Kindness podcast show.
Hi, James. Welcome.
James: Hi, everyone.
Jaclyn: Where are you calling in from today?
James: From Newton, Mass, which is like 10 minutes outside Boston.
Jaclyn: Well, let's dive in. We open up every conversation with this big question. Why kindness?
James: Well, this was a word that I lost touch with for most of my adult life during some, you know, pretty intense times in finance and private equity.
And it's a word that came. out of my mouth from a very sort of visceral, deep, intuitive place during a moment where, uh, I was actually kind of stripped naked of a lot of things, a lot of credentials and pretenses, and it was at a moment of complete isolation of, I had no choice but to be truthful. And so I think we'll talk about when that was, but the word was something that I had thought a lot about being confirmed.
When I was 12 or 13 years old in that sort of context, in a non secular context, the next time I really said it and meant it was at that moment at 42 in about as non religious a place as possible. It was in a defunct company, in a place of unknowing and complete isolation, and the words came out of my mouth.
Jaclyn: Wow. Amazing. And what is kindness to you?
James: Well, uh, I wrote a whole book about it. It took 300 plus pages. Um, there's a, there's a specific part in chapter six where I really sort of get into a little bit. Um, I first spent a lot of time debunking things. I think sometimes when you define it, what it's not, it's sometimes a good way to define, difficult to define concepts, what it's not.
So, you know, it's not what most people think it is, in that we've allowed people to define it as, um, I don't like people being defined by other people. I certainly don't like words being defined incorrectly. So it's not niceness. It's not passive. It's not random. It's not some, it's not, Courtesy, actually.
It's not thoughtfulness. Um, there are a lot of wonderful things about walking someone across the street or saying a nice thing at the right time, but those are thoughtful and gracious and courteous and nice, and I want people to be all of those things. Um, for me, kindness is much more longitudinally intentional.
Yeah, it's a, it's a real investment in a person's agency. It's in someone's humanity and it's a series of actions. It's a series of, it's not just words, it's actions. And it's a, uh, reciprocal relationship that spans time and there has to be a real investment. It's not, it's, it's not a one off deal. Um, so I, I'm an investor, as you know, um, professionally, but I think I'm an investor more importantly as a human.
I don't live a transactional life. Kindness is not transactional. It is a, I'm going to say it again, a longitudinal investment in a person where there is no expectation of direct, reciprocity, and yet there is an implicit investment in a reciprocity that is a sort of mutualism that is fast dying in this world and country where you're really investing in someone's agency and also a investment in an existing system where you are contributing a positive externality in economic terms.
So that's my definition of kindness.
Jaclyn: Amazing. Thank you. And definitely pulled so many pages from how we think about it as well. And we're on like a big campaign to eliminate random from being connected to kindness. And yeah, I get asked the question all the time, what's the difference between niceness and kindness?
And it's like-
James: They're not even in the same-
Jaclyn: Yeah, they're not even in the same party.
James: No, it's really, it's, they're very few things. I mean, I said it, you know, like I, I always pair it with kindness, with kindness, with math. And I mean, these two things after I'm 53 years old and I've done lots of different things, different cultures, and it sounds trite, but the only two things that I know to be tautologically true at this point in my life are kindness and math.
And like it's transcendent and universal and it's um, it's also a real salute to sort of Retrusting intuition which as a culture we've done a really good job Denigrating and it's um, and we can talk more about that threat will be even more Severe in this next era of like this group think orthodoxy regarding artificial intelligence.
It's just this very odd, pessimistic view on the beauty of human beings intuition. And kindness lives in that place, as does math.
Jaclyn: As it does. Yeah. Well, let's, let's go back to the beginning. I'm curious, even pre-12-13, pre-confirmation years, tell us a little bit about, like, what childhood was like? Were you experiencing kindness in your upbringing in ways that felt real and visible and tangible?
Just tell us a little bit about what childhood was.
James: Well, I'm a son of two Korean immigrants who survived a Korean War. So And who lived through the worst that humanity is capable of. Um, my mother lost her father. They, their entire country was destroyed. Both of my parents were also professional caregivers.
So my dad is, uh, was a pediatrician, a long line of doctors. And then my mother was a nurse. And so we lived in that sort of household, if you can think about it. So two people who ripped up their life came here and then were, you know, Had to learn an entire new system. We're relying on other people's willingness to invest in them to make it here There was no other way for them to do that.
They were two people who took care of people very intentionally their entire lives And then you know, they were two people who lived through a war who understands that in chaos a lot of these artificial Credentials and pursuits that we have in peacetime. They're rendered meaningless You So that's the household in which I was raised.
Um, it was, yeah, there was a real emphasis on how we did things, how we comported ourselves, how we behave vis a vis others. My mother, even though I was confirmed Catholic, my mother was Buddhist. And so, um, you know, I grew up singing Bruce Springsteen on Long Island, but in my genetics, there's a lot of Asian philosophy, which is much more steeped in mutualism than a lot of Western cultures are.
And so I, Have lived both So that's that's the environment in which I lived where we were as children really reminded and actually reprimanded more for selfishness and for just anti social behavior, like overly ego driven behavior. We were, it was not a pleasant experience in our household if you exhibited those qualities.
And many of those qualities, by the way, as a future private equity guy, those are the qualities to get rewarded in that part of my so that's the household I was Raised in, I mean, I, I named it Red Helicopter, and you know this because there was one particular moment that it just, that red helicopter symbolized everything for me, and it was just, um, you know, it was a reward that I got from a kid I was sharing half my meticulously made Korean mother's lunch with in kindergarten, and he didn't have any lunch, so I just gave it to him, and I thought I was in trouble for doing it.
I didn't know why I got the toy red helicopter from his dad. I didn't know his mom had died that summer. I just did it. And I just, I think that moment, the reason why I've named the book, this kindness and math, it is that level of clarity of just wisdom of intuition. And it's, it's a level of clarity that.
Despite subsequently having all these professional experiences and fancy degrees, I didn't have that clarity for a long time.
Jaclyn: Hmm. So you had that experience happen. It's what influenced the book, the title, um, and shaped so much of your understanding of it today. Take us through where it got lost. Why, why do you think?
For that to become the moment that defines so much of you today. Like, tell us what happened between kindness at 12 and kindness in your forties and all the things you pursued between them.
James: Yeah. So even though my parents wanted us to live that sort of caregiver life and remember, I, you know, I went to Harvard college and then, you know, I kept revolting against the things that people wanted me to be and defined as success.
I would sort of do something and then say, like, that's not impressive. And then I would go do something that I really wanted to do. And so, yeah, like my parents also wanted me to be conventionally successful in the sense of having security. Um, they, they didn't have a lot of security. And so, you know, going to Harvard or being in private equity, even though they didn't really know what those experiences were like, they were signs of security, right, of economic security, less the other types of security that are as if not more important.
So yeah, I, um, You know, they, that's a tough environment. Our society is a tough environment. And, um, you know, having a Harvard degree, as much as it may, people on your podcast may say, oh, boo hoo, that's, you know, tough life. It is a burden. When I graduated, that's a very strong brand for a public school kid from Long Island to carry.
I was much happier not having brands associated with me. I was much happier and clearer of who my, who I was, uh, being James.
And that is why I went and taught high school after I needed to, after Harvard, I needed to basically take a shower a little bit and make 12 grand a year. And so that's, that's just, and then I went to Harvard law school and accumulated just a ton of debt.
I wanted to be a public defender, and, which I am by the way, today, not in name, but in behavior, I am, and that's how things are, I don't really, I think titles and monikers are, um, very misleading, but I had a lot of debt, and so I needed to make some money, I was like drowning in debt, and so I also, you know, in my late 20s, that was sort of like the peak of my need for external validation, need for money, And I would say like testosterone driven like just high achieving guy Life right that was from like mid 20s to about 40 40 something I was living that life and not particularly satisfied either right never lost the internal james Like always had that high school teacher the kid who would share his lunch um Kid of two korean immigrants who took care of people that person never died and I never wanted him to die Um, so I spent a lot of that time sort of saying oh, it's very difficult to reconcile these two behavior sets within You know this life that i'm living and um, anyway, that's that that's where I was And so like but for the fact i married someone who really really loved me I was not particularly impressed with, um, some of these other things in environments I was living in.
Really loved the high school teacher, actually. And, but for the fact that, you know, I had really strong parenting. And, but for the fact that I had three kids of my own. I instilled the same values in my children that my parents instilled in me. I mean, those things were mollifying factors on some of the extremism that exists in some of the financial circles.
Jaclyn: The idea of that duality is so powerful. Something we talk about a lot, the idea that kindness is within every human, and yet it's something that's still a choice. It's up to each person, how they're engaging with it and activating it. When you found the I guess, uh, James with accolade winning out over James, the school teacher.
What was going on for you internally when those things were in conflict with each other, those different ways that you were living were in conflict.
James: Well, I think that, so to really put a pin on it, that was, I would say late twenties, early. 30s I think that was the peak of that where you get it's like euphoria, right?
It's like whoa Billions of dollars of money you're managing private planes like these dinners So yeah, like it was just I think that time period it was I really enjoy what I was doing for work in terms of like, I like creating companies. I like that's what I do. I mean, like it's creating jobs, families.
I treated my job differently than I think a lot of my peers did. Like, I really love creating things. But the James. During that time period, I think James personally, you know, other than the fact that I was crazy busy with work and being a new father, I was becoming less interesting.
Jaclyn: How so?
James: Well, I'm a, I'm a, you know, I have a lot of interests, right?
I'm a, you know, I think you know that there's original music on the website and I've written the book entirely as a piece of music. Like, I am a musician. Um, and I have a lot of, uh, Musical interests, uh, avid reader. I used to play, you know, tons of different sports other than golf, you know, just interesting person.
Like I just had opinions. I like going to plays and, you know, but. During that time period, and not just because I was so bogged down time wise, a lot of those hobbies became, they became overly expendable, you know, like just saying, Oh, they're not directly correlative to like a financial result. Right? That I should be reading more non fiction versus, like, reading fiction.
Like, these, all these little things like that, I think, I was just becoming less interesting. And by the way, a lot of people, like the research now, people are not interesting. Right? They have no hobbies, and which means you have no friends. Like, and I was doing a pretty good job convincing myself that I really liked to golf.
And not really realizing and realizing actually I was pretty aware like this is work
Jaclyn: Yeah
James: right. It wasn't playing golf to just I like golf, but
Jaclyn: yeah
James: it was work So everything was subsumed by work and that culture of work which um And the culture of private equity, which is different than the way that I want to really live my life and the way that I think is conducive to a civic society.
And that trend has only gotten much, much more extreme in the 20 years that has passed since then.
Jaclyn: Yeah. So I know there was quite a catalytic moment. Um, you were at Ashley Stewart and you shared a little bit at the beginning. kind of this moment that happened in your, I guess, early forties or so, um, or kind of series of things that started taking place where you realized what you were going through.
So can we walk through that?
James: Yeah, I think even before then, the more important decision, though, was actually five years before I completely ripped up my resume and my identity. I, um, I had a choice, like I was at a very prestigious private equity firm, and I had a choice. They always given, this whole book is about agency, the helicopter is a symbol of agency, and I had a choice.
It's either accept a ridiculous sum of money more than my dad made in I don't know how many decades as a pediatrician or Not take it and in order to get it. I had to basically sell my soul like be part of a wrongful termination of a person that was very close to me and eliminating him from the firm and So that was the big moment.
It was I think a week or two before my third child was born
Jaclyn: Wow.
James: And so that's the big moment that happened and that's when I, I quit. So I was, I resigned from one of the most prestigious private equity firms in Boston, um, And was unemployed and was expecting our third kid. And so I told my wife, that's what I did.
That was the most important choice actually. Um, and that happened five years before the decision of doing what I did with Ashley Stewart. So, um, and it's, people still talk about that decision. I mean, like I, I make 12, 000 a year teaching high school and I guess you, I'm not capable of And that was it
Jaclyn: with that experience selling your soul, like the idea of being faced with that kind of dilemma, moral dilemma, arguably a big one, especially if it's someone you're close with, I think, especially for people in corporate America, thinking how many times we're pushed to have to do layoffs or let people go.
Like, what do you think? Was it about that particular thing that really pushed you to realize this was the choice of this or that you could walk away from everything? Like why this one experience?
James: Well, I think it's, um, that moment, and this is where you asked me what kindness is, kindness is certainly not self eviscerating and emasculating.
It's not, it's, um, and kindness is not. Weak and it's very direct. I'm very direct I seek truth. I've been that's my whole life is about finding truth and being very direct about it so that moment was So much about what I write in the book is like it's not the what it's the how So in that partnership that private equity partnership You know, I was basically asked, are, aren't you better than this person?
And I just said, you know, your returns are better. You're more valuable to the partnership. And again, truth is, yeah, I guess in certain terms I am, and I'm more than happy for this person to be part of this partnership too, like there's a lot of things that this person adds value and I'm glad that he's here and, and I'm Makes me better, too.
We're all good. Like, I don't need the extra, like, you know, dollar bill or the extra validation. Like, we're good. And what really, I think, was, for me, the last straw was that, on the how, was, I was basically asked to tell this person that news, rather than the more senior partners telling them. And that's ridiculous.
That's cowardice, right? And that's like, that's, or hazing or that's, um, so, you know, my decision tree may have been different if the process was different, but it showed a lack of, for me, a lack of integrity. And the person deserved more than that. And so that is what that was. It was like, I don't want to be part of places that don't have the courage to be truthful and, um, and direct.
And the kind thing would have been to tell this person, you know, how do we, after so many years of being here, like, how do we help you land on your feet? It's not the right place anymore. And let's help you do this. If you think about corporate America in like general, like there are layoffs are part of this and I write in my book, the companies I'm part of and own.
I do not overly hire. I don't believe in toxic optimism. I don't do mass layoffs. That's just not that comes from like poor management. Actually, kindness does not entail birthright to have employment. There are people who should not be at a certain company is not good for them. It's not good for the company.
But the hallmark of kindness is how do you deal with that? Right? What kind of conversation do you have? You're not belittling the person. It's, this is not a good guy, or you're a bad person, good person. It is a conversation, direct conversation. You don't want to hurt the person's future, like unnecessarily.
It's not, a lot of times, you know, what, and the way I handle these, these conversations kindly is that I usually take the burden first, saying, we have you in the wrong fit. Or maybe we're not doing this correctly, or you're in the wrong role. Let's try something else. And then after a while, it becomes apparent that perhaps that's not the case.
And then usually I've found that those people who don't fit in a kind culture, uh, they know that it's not the right place for them anymore. And then there's a mutual understanding. And then you spend a lot of time trying to get them to land in a better place for them. Anyway, so that was why I left in that juncture.
It just was clear to me that I wasn't going to invest my social capital in this place anymore. So I started all my own stuff by then.
Jaclyn: Yeah. So tell us what, what came next. And I'm so curious for where you are at in your personal lives. I think it's so admirable, but I think it's good for people to hear like what, Reality means when you have your third child on the way and making such a big decision So if you could even share a little bit about that side on your personal life And what that decision meant for you and how you came home and moved forward how your wife was
James: Yeah, well the decision kind of sucked To be really blunt about it, I write about it in a book.
I was staring in the backyard and saying, looking at my three kids playing around on a old swing set and like gnashing my teeth and saying, it's creating splinters. Buy your kids a new swing set. You can afford it. And then me saying, Oh, I shouldn't do that because I'm unemployed. It's me looking at my kids and saying, did your daddy make a stupid mistake?
Like to, Yeah, this was not all like, you know, unicorns and giggles. Me, you know, making a decision like that was not some triumphant movie moment that there's like a blaring of bugles and like there's some revelation. That's not how this works. Like,
Jaclyn: yeah,
James: kindness sometimes is difficult. It's a difficult choice.
Sometimes that's what why people it's easier to be unkind. Like it is. And, um, the way, particularly the way we've designed our systems in our world right now, it's much easier to sort of like, look the other way. And we're going to get to that about what, how I design organizations that actually make it easier to be kind.
And, um, but anyway, so yeah, that was that it was a real jolt of reality that it's sort of like, I just was done living someone else's life. Yeah. You really realize in your late thirties that, you know, it's, I'm not really content with living a life that's a simulation. I'll live my own, like I'm going to build my own.
And that's what I ended up doing. And it's, my parents did that as immigrants, right? And I think that so much of the book is about, uh, an ode to, uh, the human spirit of entrepreneurship versus corporate entrepreneurship. Um, life entrepreneurship is much more impressive to me than, Starting a business from scratch, um, only, even though that does entail sort of changing your life.
Um, so yeah, like I just was very determined to sort of exercise my agency. I realized that it was, I was looking at the problem wrong. It wasn't, or it wasn't, can you be kind or be quote successful. The, the reason for a lot of my success in different industries was because I cared for people. And it was supplemented by the fact that I knew how money worked and math worked and physics works and org theory works.
And then I was able to sort of combine both. And so that's, I started doing that and starting my own platform, if you will, and investing in companies and peoples that wanted to sort of quote, win a better way. And then that's what ultimately led to Ashley Stewart.
Jaclyn: Okay. Um, amazing. I, um, and thank you for sharing that additional context.
So apologies. I got tripped up with that sequencing. Um, tell us then where you are and yeah, like what the launch was like, um, and how you're bringing that work to life.
James: Five years after that, I was doing my thing here in Boston and. Not everything is, you know, quote, clean break in the sense that I still was very much my identity to the world was still, you know, private equity guy, Harvard James.
Jaclyn: Okay.
James: Like that life that I had built that my parents had wanted me to build was still like the dominant identity. Of who I was you're meeting me today and you don't know what to make of me, right? Oh howard entrepreneur like what like author like what you know making a movie what like but back then That's who I was in people and I don't like being identified like In these simplistic ways.
I don't do that to other people either, by the way, but that's how it was. And then there was this company called Ashley Stewart and you know, it was in the portfolio. It was meaning it was owned by my former employer and I used to be on the board of that, I was still on the board and I felt accountable, like it just wasn't doing well, the company investment wasn't doing well.
And even though I was on the board, my hands were a little bit tied because I wasn't. An employee of the firm that owns the business anymore, compound the fact that it was a female oriented business. And then it was a black woman oriented business and a plus size female oriented business. You can imagine the company was not treated particularly easily by the systems of this world.
Nor was it discussed and talked about in reverential term, tone, um, I'm sorry, reverential like terms or tone by the private equity community. And I felt accountable. And I felt also just, it was disgusted actually, um, that people were so willing to just talk about it this way, but also just as a company, just let it disappear because it did a very valuable thing in the communities that.
It served, it was a real safe place for a group of women that they do a lot without much need or desire for affirmation, but it was a safe place for a group of women that worked very hard anyway. And so that's the situation. And I guess I did my little thing. I just said, you know, I'll volunteer to be interim, interim CEO for six months.
And I planned on coming back to my old identity, but six months ultimately became seven years. I mean, and we can talk about what happened and why, but, um, it's long and short of it. I underestimated how, how difficult it was to be this company, these women, and all my contacts and all of my know how meant nothing.
As soon as I let go and became part of that environment, I was treated in that way. Does that make sense?
Jaclyn: Oh, yeah, I've got goosebumps.
James: Yeah, I was basically cut off from my, my fancy resume, right? I became what I really became again, was the sauna public school. Immigrant kids again, like that. I was like, I didn't have the brand names anymore.
Jaclyn: Yeah
James: and I was sort of just cut off and um, I was shocked by how quickly that happened and uh, I got to be really close with the women which we'll get to um, About what they did for me in my moment of vulnerability and and they understood when I said to them I said, you know, I feel like i'm it's gonna sound weird I'm your ceo, but like I feel like i'm having a gift to be able to relive my vulnerability Childhood again in some ways because gosh, you really remind me of my mom you just How you are and like I watched them with their kids and like I, my mom was up against a lot of things and like would tend to blame herself for things.
My mom, you know, this country made my mom feel awfully small at times and I don't like it, you know, and I don't like seeing people feel like that. These women felt unnecessarily small. And I told them I don't I understand why you may feel like that. I don't look at you like that And so I ended up after six months I was supposed to go home because I was supposed to just save the company from being completely just dissolved And but I thought for sure people would come to help And no one came other than like two young people that came to help me and then no one believed us No one believed that like an Asian private equity guy had anything in common with black women that All of these things they doubted everything And I had made a promise I had said like ride or die.
They said ride or die and I said, yeah, let's do it And, you know, I don't talk a whole lot. That's, I'd say things once or twice and then I do them. And so I did it. And so I stayed and we won in the most important ways, like on the conventional way, sure, but like we won on her terms, we designed a system that really rewarded the character of the women that I was proud to call my colleagues.
And she won on her terms, you know, I'm getting ahead of myself, but you know, that it all ended after. My entire 40s was doing this. It was very unexpected. Yeah. But it kind of ended when my mom died, and that was it.
Jaclyn: Are you comfortable talking about that piece of it, or do you want
James: Yeah, well, the entire book is about the protagonists of the entire book.
They're all women, right? It's my wife, the predominantly black women colleagues and my mother. It's that it's not me. I was looking for ways to look the other way at times I wanted to come back and it was the women in my life that reminded me and said no. You can't do that. And yeah. So yeah, I mean, let's talk about all of it.
Jaclyn: So tell us, you're there and your mom passes, um, and what that did and how you were needing to respond or react, like what did it force you to do or what did you respond with?
James: Well. My dad had died just four years prior and you know, that was that's chapter seven of the book People have very difficult time getting through chapter seven because it was just like it's like a shocking chapter But you know the end of the book is my mom dying, you know, it's it's one of these things It's the whole book is a journey.
It's a journey like i'm an expert I guess in like Transformation processes like that's what i'm good at whether it's a company or a person an org and but I went through it You know, it always starts with yourself You And so for most of my life, I had thought my mother had lost herself sometimes in this country, right?
That, that she would doubt herself. And my mother was the type of person. My mother was a kind person. My grandmother was a kind person. My grandmother raised four kids. She was illiterate and lost her husband and raised four kids during the Korean war and put all of them through college. My grandmother was not, was a kind person, which means like she was very strong.
I don't want to say not weak because I shouldn't have to say that. She was a very strong person and courageous person. She invested heavily in other people and in her own and in the community and it made her better for it too, right? There is a, you do get rewards for this. My mother was the same way. My mother lived her entire life this way.
She was always the person that handed out the, like the biggest candy bars and Halloween. Like she always was the person that volunteered for everything for, um, potlucks and for student. Like my mom did all of that.
She never asked for any credit and rarely did she get it. Most of the times she, um, got negative things from.
her surrounding society. So when she passed away, uh, unexpectedly, I sat with her during hospice for most of her last few weeks. And she, um, I, and the book, I said, I felt the need to explain to her all the things she had done in her life, that mom, like you did all of these things and you've invested so much here.
And like, I just, and you know, she went back and got her nursing degree renewed in English. And she did it so that she could help my dad who was dying of Parkinson's, but also she went and served at a veteran's home for the Korean war veterans who saved our country. My mom lived very intentionally and there was no accident what she was doing.
And so anyway, I reminded her all of this. I remember her looking me in the eye and saying, like, Really? You don't think I know the choices I've made? You don't think I've had full agency? Like, I get how difficult it's been for me in this country. She's like, oh, your mother, the old, that woman never died.
She's here. And I remember looking down and saying to myself, like, you're an idiot. To me. Like, just like, you're an idiot. And like, I knew that, but I wanted to tell her I knew. And she knew. And like, she she knew so much of what I did with Ashley Stewart. It really struck my mother finally. She didn't understand really what I was doing.
And then she finally said, These women are me. I'm like, yeah. I was like, your little boy, uh, he has skills now too. Like, I designed an entire world and system that rewarded this type of kind behavior. Everything. Legally, economically, compensation, org theory, technologically. Like, I was, at this point, good enough to do that.
I just did everything backwards. Instead of like, you know, incentivizing people to be, incentivizing people to be better. Not kind. I just changed the vector on everything and designed it all this way. And she finally, she knew, she knew at my dad's funeral. She's like, I know what this is. Like these women are me.
I said, yeah, they are. So that was the last conversations we had. In fact, she told her friends later, her friends later told me at a subsequent funeral, I promised my parents I'm going to all of their friend's funerals, um, for them. When I'm, one of her friends said to me, you know, James, your mother didn't want to fight pancreatic cancer because for two reasons.
One, she knew the six months additional life would be very painful. Like it just wouldn't be a high quality life. The other reason she said, because she knew that her dumb, dumb son, that's me would, not leave hospice for six, like, and she just, she's like, he's got to live, he's got a family, he's got kids, he's got a wife, like he's got stuff to do.
And so they told me that she was like, because of you, like, that's because of me. And they meant it. It didn't make, it made me feel good and bad at the same time.
Jaclyn: Yeah.
James: But yeah, like that, that's how my mom, my mom lived, my mom, you know, and I'm, I'm spending what I'm doing now and I've done it for the last 10 plus years. I create systems that reward kind people.
Jaclyn: I would love to, and thank you for sharing all of that. I would love to hear, especially for like our people, our friends listening who care so much about this and are constantly living and thinking and trying to figure out what it means for them and then how to activate that in others.
What is the simplified way to tell us how you bring that work to life?
James: I'll take you back to that first town hall meeting. And then I didn't know, I'm still learning some of this stuff is, is like systems dynamics where it unfolds. So the truth just keeps rippling out and then you just have to sort of be humble enough to say, Oh, I didn't know that.
That is another wonderful thing that came from the wonderful things that I started. The ripples, right? Which is why the book cover looks the way it looks. It was that moment in that first town hall at Ashley Steward, August 2013, when I'm separated from everything that I knew, and it's chaos, right? Like, I know you know that I had to hire a police officer to protect the employees, so it was metaphoric chaos.
Which is the world. Like, there are two things I could have done. I could have said What most people would want me to say, hi, I'm James. This is my track record. I went to these schools. I've managed billions of dollars of money. I'm going to freaking tell you what exactly what you need to know. You're going to do what I say.
That's, and I'm the hero. I'm on a horse, right? I'm like air back, you know, I'm just like coming in here. Here comes the, here comes the, you know, Cowboy, and I didn't do that and, and that's not truth. And so the truth was, is what I said. I said, my name is James and I'm freaking scared. I've never done this before.
Everything that you want, everything you need. I'm not, I'm just not black. I'm not a woman. I'm not particularly fashionable. I've never run a company before. I'm not anything you need and I'm sorry. And I'm the only one who cared enough to show up. I'm the only one here. And so I'm going to tell you exactly what's going to happen.
So it starts off with just utter self. and truthfulness about yourself. Like it, it, it always starts with yourself. And so I was in a position where it would have been like absurd for me to assert anything other than the fact that I was helpless, that
I was, had no agency in some ways. The only agency I had was to be honest.
Like, I think that's the, And to care and to say that to care requires courage because caring means pain.
Jaclyn: Yeah,
James: right like to care about something to be accountable for something. You'll always be disappointed You'll always like people will disappoint you results will disappoint and your heart will break when you care It's like being a parent, but I said all these things and it wasn't like I planned all of this It was me.
Just it was I look back. It's utter acceptance of just everything not confusing wisdom from education, not eviscerating the importance of intuition versus deduction. Intuition is real human genius. It always has been. We just don't tell that story. So that's the framework. And then I said, kindness and math.
That's what I said. I said, if we can be kind and mathematically honest, And in a corporate setting for your listeners, I also said something along the lines of, you know that accounting is completely made up, right? Like it's not, it's not math. Math is science. Like we discover math. So kindness and math transcend power.
Jaclyn: Yeah.
James: It's humbling, right? And this is why like people like da Vinci and Einstein, like they, they wrote about, uh, Rousseau, Adam Smith. They wrote about kindness. And why Buddhist monks were one of the first people to come understand what I was doing. You know, a lot of spiritual leaders knew right away, but physicists did too.
And mathematicians did too. They knew exactly what I was doing. They were like, Oh my gosh, I just said, it's designing truthful systems. And so that's the thing where, you know, that's my advice. I mean, that mindset, defining kindness in math are very important for people because most people don't know the real definitions of it.
So it's nice to just sort of talk about historical context, what it is, that it's a secular concept too. Kindness that is the underpinning of agency, which is the underpinning of free markets and liberty, which was like like kindness was debated publicly in the 18th and 19th centuries and It was not a religious only thing and it was certainly not just female and that's also become that way It's become feminized and put into religious context And there's a reason for that.
Um Anyway, and so that's that And then it's, it's, then people say, Oh, and they get the giggles out or they get the discomfort out.
Jaclyn: Yeah.
James: And then, you know, it's, after that, it's really, and I think this, we can't do this on this podcast. Come visit me in the classroom, read the book. But then it's like, you realize once you're liberated from accounting and you're mathematically, Honest, you start measuring different things.
Jaclyn: right?
James: So you really start, uh, measuring things that are generally not measured by accounting because accounting can only measure it only it's made up and it measures like things that you can substantially be sure of that are correct. Quote, correct. So why I did my Ted talk about goodwill is that. We don't measure goodwill in accounting because we view it as immeasurable.
And that's a choice. So my choice when I invest or when I run companies, I actually measure goodwill in my internal, my calculuses.
Jaclyn: Love it. It's so many good things in here, and I feel like we could talk for another hour. I can't believe we're coming up on time, and I, we have like a few fun things that we like to do to round out, but I want to know, are there any other things you would want to talk about, or a question I didn't ask that you would want to speak to?
James: No, that's it. I mean, I think that to ask people to think about their red helicopter. It's a metaphoric book and a story. It's like, I'm trying to give people permission to have You know courage meaning it's nice to have it's always nice to have that person be standing behind you that says when you Exercise the agency to be kind you have at least one person standing behind you that will say I agree
Jaclyn: Yeah.
James: and that's why most people don't talk about kindness is because it's like they're still living in an extended junior high school They want to be cool.
That's not cool And they're like, Oh, that's not cool. And then I asked them, I don't know about you, but like, I don't want to live in junior high school anymore. Like, I don't want to be cool. Is that what you want to be in life is cool.
Jaclyn: Yeah. And arguably we do a lot of work with kids, hundreds of thousands of students around the country, around the world, honestly.
But for me, it's even a step further, but kindness is the new cool. It's like to be cool is to be someone who's willing to be kind, which means to be courageous, which means to stand up for what's right. Like it's helping completely reorient how they're understanding these things so that when they're choosing it.
Right? It's all connected. Um, so I love that.
James: Yeah, it's closer in line with their intuition. I mean, one of the funny things is this, during my, when I was doing drafts of the TED Talk early, I, I ultimately didn't use this because it was too dark. Like, I said the, one of the first opening lines I was gonna say was, I think we should stop lying to our kids.
I think we should rip up all of the kids books. And just tell them you're going to grow up and be and not trust your intuition You will grow up and be rewarded to be a jerk and to be a peacock and so and character and like Integrity they will not be valued and I said that maybe if we do that kids will be will grow up to be a more docile workforce And they'll we can have more profitable companies And people will be less miserable at work because they're expecting misery.
And so it was the general consensus amongst My team and the Ted people, they're like, it's a little dark, but I was like, but it's true, isn't it? So the word underneath in my message that is like people were shocked, right? Work is the blank leading cause of death, depression, suicide. Everyone hates their job.
It's not about remote work. It's part of, it's not, it's a much more. Like existential question about like, it's this cognitive dissonance. It's like, we're, we're not what people are wired to be selfish and like, not great sometimes, but I have a lot of optimism generally in people. People don't want to be unkind.
It makes them ultimately feel very bad about themselves and they drown it out with you name it. Right. Oh, free yoga.
Jaclyn: Yeah.
James: Or they drink, or they do other vices. They, people are not, are not feeling good about themselves. And that's sad.
Jaclyn: Yeah. So much wisdom in there. So much wisdom. Thank you. Um, okay. So we love to do like a round Robin of questions where I just say a question, you respond like very quickly.
So kind of like one word, quick answer.
James: So it's like password, remember that game password?
Jaclyn: I don't know if I do.
James: The triangles? Or the hundred th Oh, the hundred thousand dollar pyramid, remember that?
Jaclyn: No! I'm gonna look it up though.
James: You were much more productive as a kid than I was. I was watching dumb game shows.
Jaclyn: Um, okay. Define kindness in one word.
James: It's an upside down hedgehog.
Jaclyn: I don't know if I've ever had to have anyone explain their definition of kindness upside down hedgehog.
James: Yeah. So in chapter six of the book, there's a drawing of an upside down hedgehog where my kids wanted a hedgehog.
Jaclyn: Okay.
James: And I said, You can, I did the research, but then like my dad, I tend to go off onto these stories.
I'm like, I said, kindness is a lot, like try to live your life like an upside down hedgehog. I think kindness is that where you're living with your belly up exposed. And it creates real clean lines of sight, less bias from you, less ego, you see truth. And then my kids would say, but don't people sometimes stick sticks in your belly, dad?
And I say, well, yeah, I take it out and then I give it back to people. I looked them in the eye and I asked them, did you intend to do that? And I said, do you see what's on my back?
Jaclyn: Mm hmm.
James: It like don't mistake this for weakness like really and i'm i'm watching how you react to my kindness. It's game theory, right?
I'm, i'm watching your how you react to me being belly up.
Jaclyn: Yeah,
James: what type of person are you
Jaclyn: amazing.
James: So it's an upside down hedgehog.
Jaclyn: Okay, if you could get everyone around the world to do one kind thing What would you have the world do
James: I think I would say to never forget to be a teacher and to say thank you to your public school teachers or like to advocate for teachers.
I think teachers are kind. It's a kind profession. So that's what I would say.
Jaclyn: Uh, if kindness were a song, what song would it be?
James: Oh, that's an easy one. I have an original arrangement. Okay. Yeah. So there's, um, I think, uh, kindness is, uh, the song on my site. It's called Adidong Amazing Grace. It is a, it's that it's also to, and these are two folk songs, but it also is this it's, um, to put a little Springsteen in this, it's an anthem.
And so it's the second verse of Born to Run. So when Bruce is singing, he's singing, um, will you walk with me out on a wire? Because baby, I'm just a scared and lonely rider, but I got to know how it feels. I want to know love is wild girl. I want to know, is your love real? And like, I've always viewed that as that.
It takes a little bit of a leap of faith and to be vulnerable. And he's asking like, I got to know how it feels.
And so that I think is something that, um, I would say.
Jaclyn: Who do you credit for inspiring kindness within you?
James: My parents, but particularly my mom. That one's just, My mom and I had a very special relationship.
And I was not the prince. It was not like that. Like, she held me significantly and seriously accountable.
Jaclyn: Um, what book are you reading? Besides Red Helicopter.
James: Um, you know, I'm finally getting around to reading, uh, Tara Westover's book, Educated.
Jaclyn: Oh, great. It's a great one.
James: I'm really, really enjoying her journey, finding her agency and truth, which is what that book is about.
Jaclyn: Okay. And then we like to end always with action and what it means to have that agency to choose kindness. Um, so hopefully you are prepped that we have everyone think about someone they want. To acknowledge, send gratitude to let them know what they mean to them. And we have, people will call someone, you can tell us who it is, and you could send a text message or reach out to that person after, but we open it up and let each guest decide who it is.
Um, and then how they want to reach out and let that person know.
James: Yeah, I would, I want, I want to sort of. send a message to my, my quote, kid sister. Okay. Um, she's like my mother in many ways invests in everybody, takes care of everybody, makes everything better for everybody. And like most kind people do not ask for credit.
They don't ask for, um, And so, um, I just want to remind her to that I see it and that she needs to make sure that she continues to also invest in, um, her, herself and her, her. can't take care of everybody unless you're taking care of yourself too. And that's not,
Jaclyn: yep.
James: Just can't,
Jaclyn: can't pour from an empty cup, beautiful. Well, we'll be eager to hear how that goes.
Outro: Thank you so much for joining us on this week's episode of the why kindness podcast to learn more about everything you heard today from our wonderful guests, definitely check out our show notes. We hope you're leaving this episode inspired and reminded that every kind act truly does make a difference.
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