James Rhee, a high school teacher, Harvard Law graduate, private equity investor, and the unexpected Chairman and CEO of Ashley Stewart, joins Zibby to discuss RED HELICOPTER—A PARABLE FOR OUR TIMES: Lead Change With Kindness (Plus a Little Math), a brilliant business handbook that elevates kindness, joy, and goodwill. James shares what he learned from his Korean immigrant parents and from the black women he worked with. He reflects on the challenges faced by Ashley Stewart, weaving in themes of race, gender, and systemic barriers. He also touches on grief and the importance of embracing emotions in the workplace.


Zibby: Welcome James. Thanks so much for coming and Moms Don't Have Time To Read Books to discuss Red Helicopter, lead change with kindness, plus a little meth. 

James: Thanks for having me. It's nice to meet you.

Zibby: It's nice to meet you too. What a powerful book you wrote. I mean, it's a unique hybrid of sort of the business y side of stuff, but mostly the emotional side, which of course is That's the point, right, that we have to bring it all together.

Can you tell listeners what the book is really about and how, you know, when you decided to write it, which of course you write about in the book. 

James: Yeah, I think the book at its core, it's about a son and his relationship with his parents, especially his mom. Um, And really understanding the gift that his mother gave him regarding agency and him not really fully understanding that gift for a long time. and then it was how a group of women, most of whom were black women who really unexpectedly gave him the gift of understanding that agency through his relationship with them. And realizing that I had the opportunity to do. I think better dropped the wrong word just to really appreciate it in my 40s about some things maybe I missed when I was younger and how the parallels between these women and my mom.

I think lastly it all plays out you know funny enough in a business story. And so while I'm unlearning and relearning, I get the opportunity to expose a group of readers who might not generally get exposed to private equity or finance and make it accessible to them and also affirm them and say some of the things that might be troubling you in your lives.

Some of them are not of your own doing, that there's systems around that If you understood them better and we helped name them for you, you would realize that what you're doing in life is quite extraordinary. I think that's sort of the book. It's those three woven together and yeah, I think it's I think that's what it is at its core.

And that's why I couldn't think of a better name for the book, because it has all of these things. And I know I was reading I was reading about your bookstore, about how you curate based on emotion, which is like, which is brilliant. It's really trying to marry emotion. We are emotional. I mean, human beings are, and I think a lot of times in our culture, particularly in the U.S. We think of emotion as weak or not natural or, but physiologically there's just not true. 

Zibby: So yes, especially in the workplace. Someone I worked with yesterday forwarded me a whole thing about you and was like, this is, this sounds like. What you do that be like, it's okay to be kind and nice. Cause like, you know, every job description we post, it's like nice people only, you know, like I don't have time.

And I was like, no, I'm interviewing him tomorrow, and she's like, of course you are. Um, but it's, it's so important and not discussed enough, right? Like bringing our whole selves to what we do and the scene in your book where the women who, um, were the store managers for Ashley Stewart, who came to your, your father's wake that was, and you were sobbing.

I mean, um, I was like, oh my gosh, don't cry. I don't have time to cry. But so moving, right? That like, they were like, of course, we're going to show up for you because we're people and we show up for you and you show up for us.

James: I got so accustomed to not expecting that and that's part of the sadness in the story is that I grew up.

That was normal I think we most of us do as kids. It's it you should do that and investment of time and heart. There's nothing more Valuable nothing that lasts longer and I don't know about your listeners. I'll just say to me I had a hard time I forgot that a lot in some of the workplaces that I worked in it's um, and particularly being a guy I think that that there's that strain to which I talked a lot of You Mothers these days about their sons about that son's getting worried about just they're like that we worry We will lose that side of the Sun.

So yeah, and then they reminded me They said of course, we're gonna come and hug your mother and hug you and like why didn't you ask anyone for help? Why didn't you tell anyone and I think I wrote in the book. That was the last moment I just said all the armor at that points off. I just said I don't want to live like this anymore. 

Zibby: Yeah, it's amazing.

I was really struck. I have four kids and the scene where your daughter Lila got into an accident at day camp and how it was sort of, you know, not even the people who were running the camp and the trustees and everything, nobody even talked to you, including people you had relationships with and, um, the fear and everything she went through.

Can you just talk about that? And I know you said she's totally fine now, but everything's fine. 

James: Like Totally fine. I mean, she got, we got lucky. I mean, she should have, she should have died. And, uh, yeah, it was, uh, just a local day camp. We, you know, low expense structure. This was not a fancy camp. Yeah and so she got hurt in a camp accident.

She wasn't supposed to be doing what she was doing. Everyone knew it. And instead of helping the doctors figure out what exactly happened, everyone circled the wagons, right? So board protocol, this is what happens, the attorneys advise, you can't admit anything. Some of the board members I knew from just my business life in Boston, and I was a bit of a mentor to one of them.

I just couldn't believe that he didn't call. And I get it too, right? We learn that there's a different way of living once you become a doctor. Quote become a grown up. There's a grown up way of living and particularly if you're in certain business worlds there are certain rules where that trump the rules of humanity right that there are different rules So you have to play by these rules and I think part of the book is just asking people to just pause and say Like really like is that really what you should be doing?

But yeah, they didn't call and I'm glad because these younger board members they had a catharsis themselves, right? Hey They realized that they just sort of came to grips with their own cognitive dissonance and saying, I would never act like this. Like, why am I acting like this? And there's so many behavioral primes that are hidden and ingrained in our just norms and laws and systems and mores.

And I hope the book does a decent job just sort of showing that to a lot of people who, again, they tend to blame themselves. 

Zibby: Mm hmm. 

James: They don't know. And I'm saying, you know, if once we name them, is there an ability to maybe just adjust our behavior modestly? If all of us do it modestly, it's like that scene in Finding Nemo when all the fish swim down, not asking for like 180 degree behavior change.

It's maybe like, you know, can we 1 percent each and then all of us do it. And I think some of the mores that we are, for some reason, having a hard time sort of just coming to grips about with some things that are kind of right and wrong. Like, I think maybe we start from there. 

Zibby: I mean, I think what you said to the former mentor, when you said, what happened to you?

I mean, first of all, that reflects so much on you, like to, to get in front of someone who's had, who's responsible for something that happens to a child, and instead, like, turn it around. Like, What happened to you? Like, and I think that's really what you're asking readers too, right? What happens to us along the way?

And can we stop? And like, you know, let's all wake up, which, you know, just to paraphrase.

James: My publisher, Judith, she's, I give her all the credit for coming up with the subtitle of a parable for our times. I, after she had read it, she said, it's a parable. And I said, exactly. I said, yes, it is a parable. It's a lot of interlocking stories.

It's in musical terms. I tried to write a fugue. It's a lot of repeating circles and stories like repeat and over and over again. And they just keep getting bigger and bigger and bigger and bigger. And at the end, I try to tie it all together. But it's not a prescriptive book. It's hopefully it gives people permission to just reflect and it's not telling people to do better or telling people to do something in this way.

It's more like maybe you should trust what's instinctive inside. You know, you have it already. So what do you think? 

Zibby: Yeah. You also have a touch of the, you know, how the universe works and the things we don't know, you know, everything from, you know, I think that, you know, My, you know, my parents are, they're here feeling the spirits when they're not there and like the numbers, like you're 20, you know, twos in the hotel, you know, at the hotel hospital rooms and happy almost birthday, by the way, all of that, that there's something bigger at play and that we have to be aware of that as well.

James: Yeah, I tried to, I think growing up partly because I was all parents, but I think I was the first one born in this country for, um, in our family. I think there was a little bit of an extra emphasis on figuring it out, learning the system. assimilating, like it's really learning the rules. My parents really couldn't help me.

And I think when you grow up like that, sometimes creates a desire to over control, over prescribe, and that I have to do these things, these paths. And yeah, I don't know if I was particularly happy actually doing that. And, um, During my 40s, which is the time period this book centers around, I realized again, it's like, you know, just not being in control and letting things be serendipity is beautiful and just letting things unfold.

That agency actually entails surrender. And I couldn't say that without you. 10 years ago, but now I can like, I'm like, I understand what that oxymoron means that you just have to let go and yeah, let go with a soft hand on a little bit, but you have to let go and let it flow. 

Zibby: So I, I learned that this past decade also, actually my husband was switching careers and I was like, okay, well, how are you going to get a job?

You know, in entertainment. And he was like, you know, it's all just going to unfold organically. And I was like, no, it's not like, that's not, you know, I'm like, you know, this and the resume and the schools and like that's not how it works. And he's like, that's how it works for me. And I've kind of adopted that. And I'm like, you're right. Like when it does, when you let it work like that, it actually can and people are like,... 

James: Well, look at the path that you've led. I was just, it's you, when you look on your website and all the things that you're involved with. You couldn't possibly have planned all that. 

Zibby: No, I know.

I know. Thank you for researching that by the way, that's really kind of you to do. You wrote really beautifully about your wife. I feel like she becomes a big character in the story and you know, everything from the beginning through to your in laws to, you know, different things that she does at different times and your, Really just huge respect for her.

How was she in the writing of this book? And were you just talk about making someone you love into a character? 

James: Yes. So I think like other authors, I'm a first time author. I underestimated how hard this process was. It was really hard. I think I was, I publicly excoriated myself. I think it was on like Brene's podcast and saying, I don't think I can do this.

Um, but she, um, she tolerated. my insecurities during a lot of this writing. My wife is the CEO of Cure Alzheimer's, so she is the scientist, like, empiricist in our relationship. So it's funny, like, in other relationships I have, I am the math, rational person. In our relation, in our relationship, I'm the creative, and I have that side of me, and I think it took me a long time to realize that, but yeah, I'm the creative that wears his heart on his sleeves and says, Oh, I can't do this, I got to go play my guitar and like, I can't write anymore. And she was very patient and they were looking back. There were times I would not, I would not have been as patient with me as she was. So, and there were times she said it, she's like, uh, you're annoying me right now. But she was just a real thought partner.

She's a great writer and I also wanted her to really read it from my children's perspective, too. I didn't speak about my children. I wanted to make sure there was nothing in it that would be, um, longitudinally, like, bad for them, embarrassing for them, that my daddy wouldn't. Embarrassed them, you know, she's been a rock for me our entire life.

I mean, it's um, I am my best self with her That's so nice. I Like and I want to be that like we all have not great parts of us I want to be I want her to be proud of me and that feeling that sort of motivation Yeah, that's one of the few times I've had that in a relationship And I was like, we should get married.

Like, so. Maybe I should keep 


Zibby: part going. This, this must be good. 

James: It's hard to find those people in your life. You know, that you really don't want to disappoint them. And you want to be better. And The book is all about those people, right? It's about, yes, people who made me better. 

Zibby: Yeah. I mean, the, when you talk about Ashley Stewart and going in and like, it's like a case study, right?

I went to business school. It's like, what happens with this case? Like where, where do you start and why was it verging on bankruptcy? And then, you know, the camisoles in the back room and trying to like piece it all together and how did a company with A fan base, right? And a loyal audience get into this situation.

When you were tying together this exploration, sort of the deep dive into the company, did you do that Um, to also like parallel as you were diving deeper into yourself and you wanted to, to show the different strands. Just tell me about like, were there any pieces of this overlapping story that you thought were not essential or essential or, I mean, there's, cause there's a lot going on, but it all weaved together perfectly.

But when you were thinking about it, I would imagine that would be a hard sort of outline at first to, yeah. 

James: Yeah. It took me some time to really digest. I mean, some of this, like we were talking about sort of what the light that you've been leading, it was, I had to let go and allow, I mentioned fractal theory, just allow the chaos to unfold.

Just the more I let it go and trusted more intuitively, what was the matter? I learned more. It took me a while and it took my mother's, unfortunately, death. And then. Many years of me mourning my, my mother to really write this book too. So some of these Eureka's came while I was writing the book. I didn't really fully appreciate.

I knew that the women reminded me of my mom while I was, I knew that sort of as a finance business person. Having lived through sort of like the standard capital market, standard systems. There are better people than me to talk about this, but I, I knew that the systems didn't reward people who create positive externalities.

Which generally skew female, by the way, right? So I knew all of that and I knew that one of the things that was holding this company back was all of those things. Layer on race. , right, that I knew and I knew also that my mother tended to blame herself a lot for not knowing things or fe she feeling misfit or wrong when I would say, mom, that's not you, is.

It's not easy being a Korean immigrant woman who doesn't speak English in this country. Look at all the things you've done. And that I knew, but it took after a while just that. I think what really happened in a nutshell, it's, um, it was a predominantly group of black women who actually, Also reminded me and taught me about my Korean heritage.

And it's, that's a identity that for growing up and even throughout my adulthood, mostly it was been my Jewish friends who have reminded me of my Korean heritage. And it's always been that way for me on Long Island and, you know, in school and up in Boston, New York, but really like this last linchpin in my forties.

It was black women who really, they loved a lot of the Korean ness in me, actually. That part of it, that nuance, I didn't understand while I was doing all this. And then now I think I better understand what happened. 

Zibby: So interesting. I didn't realize in Korean culture that they said it takes about three years to mourn, that you should mourn your, your parents or mourns, yeah.

I think it should definitely be more widely adopted. I mean, grief in itself is, I mean, there is no timeline, but giving yourself that external permission to let it take a while and to, you know, you took time off to figure out what to do in that period. And it's something that people should hold onto, right?

That it's okay that it's not going to happen in two minutes, that you can just take a week off of work and jump back in and everything's fine.

James: Now, one of the words that I think you would especially love in Korean is, uh, it's called, it's, it's maum. So in, in Korean, maum means literally heart and mind. So it's less like Aristotelian.

There's not a distinction between the rational and irrational and cognitive and emotional. So parents will ask you like, maum deureo, like, what does your heart and mind tell you to do? And that weave and that sort of, uh, fluidity, a lot of that is less common, I think, taught or encouraged here. Mm hmm. And I think that's one of the things that people are struggling with even now when people ask, you know, What do you think of the economy?

And people are not happy. And they're like, Why? The numbers are so good. You know, people are emotional. Mm hmm. I mean, this is I think that's one of the things over the next 10, 15 years, I hope that our culture here is more realistic about just emotion. Yes. And it's powerful, right? I mean, it's really empathy, vulnerable, all of these things.

And it's made me I think a better, I know a better person, but even in my investment life or business life, I think I'm a better investor. I, by trusting intuition there, we're at huge inflection points in our society. And some of the things that are about to come upon us are not quote rational, like major changes that are happening.

And some of that you have to sort of delve into imagination a little bit and say what's possible. So I thought Maum I think would, I think I bet when I visit your bookstore one day, like I bet it feels Maum. 

Zibby: Definitely visit the bookstore. We'll do an event. We should do an event for your book and you know, don't just pop in, but let me know.

I will. That's amazing. When you're not, you know, Working on, where are you going after this? You're now a TEDx speaker. You have this fabulous new book. Like you, you can become this guru, right? With like guiding life's paths and thought leadership, blah, blah, blah. Is this what you want? Like, I, cause I, I, there's so much time in the book where you spend trying to think of it.

It's like so meta. You're thinking about what you want to do and, you know, judging what you want and da, da, da. Like where, Where do you want to go? 

James: I love that question. I think for lots of my life, I was doing things not that I wanted to do, that it was sort of that I was supposed to do. And I kept struggling, right?

I went and taught high school and then I did this and I was fighting myself. You know, what I'm envisioning is this, and it's, I'll use less business talk and like business model, just more of a life. I want to put my life at precedent, like at a premium. So I'm living my life. It's the life I want to lead.

It's the legacy I want to leave, not from a business standpoint, from my, but my relationships. I'm going to really center my family, like real friends, make new friends. So I'm looking at the next 30 years of my life as if I were 22 again. So from 22 to 52, you know, like I was so awful at so many things at 22.

And then by the time I was 52, hey, like pretty decent on a few things. So I'm doing things that I'm terrible at, at 52. . . Maybe when I'm 82, like I'll be pretty good at it. And so I want to live like that. I think I'll keep my brain fresh. And then the second thing, but Red Helicopter is, it's hard to describe.

It is Goodwill. It is Chung. It is this brand. Like I know how to. to as an investor, it's a brand and a physical object that I hope people will say all the things that I want for my children, all the things that could be slightly better. Maybe it's too complicated to talk about and people are having a hard time speaking right now.

If they see a red helicopter, we can be that. It's like a branded philosophy, almost. A branded operating system. And so, with an operating system, there's a community around it, and you know about building communities, and it creates new orthogonal, like, relationships. You know, I teach at Howard, MIT, and Duke.

And it makes complete sense to me, you know, I have my friends are like, it's the United Colors of Benetton, and it's just, I live that life and I'm asking people and saying it's more typical than you think. And so why can't be like this and then. So it's a philosophy it's a teaching system, I hope that a lot of people will want to read the book and then I really want to have permission from adults to speak to their children.

I really hope that this is a book that adults read and say to a 20, 25 year old, something like that, and saying, you know, this is a good framework of a curriculum and a life. I don't want to speak to the kids without getting permission from their parents. That's the way I wrote the book. The book. I think where Red Helicopter can go, you know, it's, um, where it's going is that it's a curriculum about life, money, joy, and about agency.

Yeah. And then from an investment standpoint, a lot of the entrepreneurs, and I tend to overly like the numbers are more women, they're more people of color or more first generation college. And I tend to invest in them in every way. Now, it's sort of a network, opening doors, a guide if they need one and money.

Um, but just because I don't give them money doesn't mean I can't invest the other three things. So that's what it is. It's like a branded world that has media teaching and part of my investment life too. 

Zibby: So great. I love it. 

James: Kind of can you see it?

Zibby: I can see it. I can see it. Yeah. Like the blades of a helicopter.


James: Yeah. I love it. I hope, I hope that, you know, it's been part of this whole process for me. It's been rediscovering my music. I think if I'd had more courage, I was born in 71, right? So I didn't know music and movies and like, that was an option for me. feel like one. But I think now, as I think about it, I misdefine what being a creative means.

I thought it just tangibly meant you drew or you, but it's more of a frame of mind. And so that I sort of accept it. I'm like, I'm a, I'm a creative, a little bit of a romantic, a dreamer, right? I sort of, I like creating things with people and sort of making things a little bit better for people that sort of.

Who I am. Um, so yeah, I'm enjoying that side of it. So the music's been a really important part of me like a lot. This book is actually written. It's a musical. Yes, you read that in the, it's written in E flat major. Actually, I remember meeting the Harper one team and saying, I think I would like to write a few again, E flat major.

And he's very polite. He looked at me. It's structured as a musical piece and there's three movements and, um, Yeah, and so we compose music and arrange music with it. We'll release it too. And so that's a lot of the projects I'm working on right now is, can I help people learn kindness and math together?

And then the way to deliver it is through art. Because art is art. Forces you to use both sides. And it's making sense to me now. I'm like, ah, this is why I have to convey it through music. And I'm commissioning some art pieces to draw what the music and the book are. So I hope it encourages young people to contribute their artwork or music.

And, and again, make some of the money stuff. more accessible to some people who are frightened away from it because of the way that it's taught or the way that it's structured in our society now. I think we can do a better job making it more accessible and it's not just quote dumbing it down, it's the way in which complex principles are taught.

I think we can do a better job. 

Zibby: Okay. Well, it's really exciting and original and needed. So, I'm a huge fan. Congratulations. And the book itself is, is really wonderful. And especially the relationship with parents and grief and appreciating where you come from and all of that. It's, it's very poignant and moving.

James: Thank you. And I look forward to, uh, March 1st. Aw. Yeah, you have a big day coming up. Right? You know, I don't have a podcast, but I would love to be helpful in any way that I can be and I'd love to meet you in person and Santa Monica's awesome. Yeah. So, is that where you are? Is that? 

Zibby: I'm in New York. Um, I'm in New York.

I'll be in L. A. tomorrow, but yeah. 

James: And your name came up sort of serendipitously involving a organization for women. Writing. 

Zibby: Oh. Okay. 

James: UWM. Girls Write Now. 

Zibby: Oh, yes, yes, yes. Yes. Yeah. 

James: So, sort of serendipitously, they came into my inbox through some probably mutual context that, but separate from this, and they mentioned you.

And I was like, oh, I'm gonna meet her today. 

Zibby: Oh, there you go. Perfect. 

James: Congratulations on all that. That's amazing. 

Zibby: Thank you. 

Thank you. And really, honestly, thank you for even doing any, spending any time getting to know who I am. So that's really nice. 

James: It's great meeting you. Bye. Thanks so much. 

Zibby: Great to meet you.

Thank you.


Purchase your copy on Bookshop!

Share, rate, & review the podcast, and follow Zibby on Instagram @zibbyowens