#434: How Unlocking Kindness Will Grow Your Business with James Rhee Teacher, Investor, CEO, National Bestselling Author, & Founder Of red helicopter
4 Nov 2025 · 47 min
James Rhee, a high school teacher turned CEO and investor, talks about how kindness drives business growth. He shares his journey leading Ashley Stewart and building Red Helicopter, connecting personal transformation to leadership philosophy.
Chapters
That first speech I gave to the women at Ashley Stewart, I said to them, I was like, I'm probably the least qualified person to run this company. I'm none of the things you need. Female, fashionable retail executive, all these things. But I'm the only one who showed up. I'm the only one who cared enough to be here. And so when I said that, people who mistook that for lack of confidence were wrong. I think that's real confidence. Like I know what I'm not. I don't have to pretend.
Come on this journey with me each week when you join me. We are going to chase down our goals, overcome adversity and set you up for a better tomorrow.
Fasten your seatbelts. I'm ready for my close up.
Hi and welcome back. I'm so excited for you to be here this week. Our guest this week is James Reed. He's a high school teacher and Harvard Law School graduate turned private equity investor and CEO. James's leadership story first grabbed global attention during his highly unlikely seven year tenure as chairman and first time CEO of Ashley Stewart. More on that suit after his radical and yet intuitive approach fueled a transcendent, unprecedented reinvention story for the company. James concrete his eyes. Well, that was a big one. His leadership philosophy and operating system kindness, plus a little math in the form of Red Helicopter, his media education platform. He bridges math with emotions, 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 organization. Re teaches at Howard University where he serves as the Johnson Chair of Entrepreneurship, MIT Sloan School of Management and Duke Law School. His TED Talk and dare to lead interview with Brene Brown have captured the imagination of millions. He's the author of Red Helicopter and lives outside of Boston, Massachusetts. James, thank you so much for being here today.
Hey Heather. That was good. I think concretize is a very odd word. I should sort of get rid of that word.
That was a tough one to spit out, but I'm glad we got through it. Your accomplishments are incredible. What is so cool is just getting the chance to know you briefly as you and I were sitting here talking. You are such a chill, laid back, not in your face person. However, your bio. No one would be able to know that when they hear about all the accomplishments that you've had.
What's the expression? It's like, is it the real G's move in silence? Like, I don't know, like it's. I've learned over the course of My life. I don't take myself very seriously, and I'm getting better and better as I've gotten older, but I take my relationships with people really seriously.
That's good.
I laugh at myself a lot, but I don't laugh at other people. But hopefully create relationships where they feel comfortable laughing about themselves too.
Yeah.
And fundamentally, the foundation of the way I live.
Well, it's working, my friend. It is working.
All right.
Since we only have a finite window of time with you, I really want to get into this. I love the book first and foremost. But I wanted you to start, if you could, telling us about this kindergarten story for everybody who hasn't seen the TED Talk, who hasn't read the book yet, so they can understand where this all started.
So on the COVID of the book, there is no red helicopter. Because I'm asking everyone, do you have a red helicopter story? But for me, it was literally a red helicopter. I was a five year old kid with a bowl cut, Big dimples pictured, Long island bowl cut. All right. And 1976. So I'm 53. Holy crap. And I came home from public school, like, it wasn't easy in the re household in 1976. We were not swimming in anything, actually. And I had a toy and my parents were like, why do you have a toy red helicopter? And they thought I stole it from school. And then, you know, I got nervous. I'm like, no, I didn't. And then I got it from a family. And then they said, oh, we didn't know in America you're supposed to give gifts in kindergarten. So we're so sorry you felt left out. I'm like, no, dad, mom, I'm the only one who got one. Just a family came and gave it to me. Anyway, series of, like, things that you think you're wrong and errors. But they found out that I've been sharing half my lunch with this boy in my kindergarten class because he never had any. And I thought I was in trouble the way my parents were asking me about it because, you know, we didn't have a lot of money. Or maybe I was being unappreciative to my mom. Anyway, so it's one of the last times or a few times I saw my dad really emotional because I think, guys, we have a hard time expressing emotion. We still do. Right. In 2024. And anyway, he said, you know, the reason why your friend doesn't have lunch is that his mommy died this summer. And I'm not mad at you. Like, I'm proud of you. And he said that. And I've always thought about that story because it's so easy now when you get older and you start overthinking things and you're focused on credentials or accomplishments. And you know this, at some point as an adult, it gets burdensome. It's like you get tired. And I was like, I always wish I had the wisdom of that five year old kid. I just, it was so easy. Like we didn't have a lot and yet I lived so abundantly. Like I was so generous. Even though I didn't have anything, I didn't care. Like he didn't have food. So I give him half your food. It's okay. I wanted to live like that. At the same time, I've lived a life, you know, like some of the things I've been in, communities I've been in is high performance, high achieving, and people self obsess. And I was guilty of that too, you know, and I didn't want to. And so I didn't like it. And so that's what the book is about. Can you sort of have that generosity and wisdom of a kid? That love of life, imagination, learning? And as an adult, does it actually if you can keep those qualities, does it make you more effective, more insightful, happier, more charismatic, more imaginative? And you know, I'm asking the reader, I think it does. And so, and I lived it during my 40s, like I refound that kid, but I didn't lose the skills, you know, kept the skills. But remember what it was like to be wise like a child.
So how did you lose it and then come to find it again?
You know, look, up Until I was 18, I was a public school kid from Long island whose parents immigrated here. And that was my resume. Other than the fact that in work experience it said Red Lobster washed dishes to earn enough money to take girls to the mall to buy them Orange Julius. That was one experience, okay? The other experience was bust tables for $2.35 an hour plus tips at a restaurant that looked like a ship in Port Jefferson, Long Island. That was my resume, right? And then interests, music, sports, that's it. You know, then you start going to schools and like the college degree, like it says Harvard now. What's that mean? Okay. It's an overwhelming brand for a kid like that. I'm like, great. I got good grades, a great. I got into Harvard. That's so what, like what am I going to do with it? And so I kept fighting it. So after I graduated from Harvard, I think, you know, I went and taught high school for 12,600 bucks a year, right? Was so grateful that my parents, like, leveraged the crap out of their house to pay for school. I was like, oh, other kids, this was nice to go to college like this. So I taught, and then I went to Harvard Law School, be a public defender. It wasn't like I wanted to make a ton of money and stuff, but then I ended up being in private equity for a long time because I hadn't grown up with money. But it's important to know how money works. Like, that's part of life. It's not like, you know, I'm not recommending people to live in a cave and be an ascetic monk. Money is part of the equation, right? And then so during those periods of being private equity and, like, Wall street, like, swashbuckler, that image of, like, this is whatever. So I like managing money and, like, investing in companies. But it's, I think, different for me than maybe for most of the people in the industry, because it's cool creating companies and, like, creating jobs and what a gift to be able to be in a position to do that. For me, you know, it wasn't about just trying to, like, wring the last nickel out of everything and, like, trying to hoard wealth. I've never been wired that way, but I know how to make money, right? So during that time period, I had a lot of, like, dissonance. I'm like, oh, you know, I'm a high school teacher. I'm a pretty loving guy. Like, you know, I think sometimes guys have a hard time saying that too, right? I care a lot about people. I really do. And I used to be ashamed to say that, and I'm not anymore. Like, I really love people, and I know how to do things that make money and build. So that was where I was. And then it all came to a head in my early 40s when I was a dad of my own, and I was having, like, not a midlife crisis, but just really thinking about, like, okay, what do I want to do now? And then my dad was dying of Parkinson's. My dad was a pediatrician with a single shingle. He took care of so many families. My dad was a quiet hero. He really was. And my mom was a quiet hero, too. She was a nurse. And then there was this company that served predominantly black women who. They were quiet heroes, too. They took care of their families, worked hard, and, like, they weren't asking for any credit. And you can imagine the business wasn't treated very well, I would say you can imagine, right? And that's where I was. It was like a Les Mis moment. Like that Valjean, like, who am I? Like what am I going to do? This business is about to liquidate. All these women are about to lose their jobs. This is not a normal business. It's like a safe place. Like the women congregated there. They would spend time. It was like a breath of fresh air for them because they had so much responsibility. And all the time this was the one place they could actually be a little bit selfish. And I saw it and I couldn't unsee it. And so I left my life. So for. For my entire 40s, basically, I was the CEO and like big owner of a business selling fashion in urban locations for predominantly plus sized black women. And for your listeners, I'm an Asian dude in Boston and like private equity guy. And like, and I'm not fashionable. I dress like crap. And that's what I did, you know, and like the whole world was like, oh my God, like what's going on? And but it made sense to me. Like, I was really grateful for their friendship. The women reminded me of my mom, you know, and like, just, they were really decent people. They just hadn't caught a break and that they didn't know how the financial systems worked. And so I basically said to the women, I'm like, just be yourself. You guys are awesome. Like, I know some of these other things. Let me tinker over here and let me design a system that rewards the type of behavior that I see from you, which is like high character team people who create a lot of value and don't ask for credit. So I rewired the entire company to reward their pro social behavior, you know, Then I put in money and then technology to amplify it. Next thing I knew, people were like, holy crap. Like, it's awesome. And we did really well. And like financially we did really well. But it wasn't, it was almost like a second thought, you know what I mean? I'm like, I was more proud of the fact that people wanted to be part of us. Every race, every age. They're like, we really love your guys. Friendship. How nice is this in a world that kind of sucks sometimes? And so all of these people came to want to be part of it. And yet titans of Wall street and tech companies, like, we broke them down. Like they were like, yeah, we're tired too. Like, how nice is this? And do you guys have a real friendship? And I was like, yeah, we do and that's what I wrote about and I'm asking the country sort of do you miss a little bit of this sometimes?
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I asked you to try to find your passion, James. One thing I want to go back to because you gleaned over so much right there that I don't want everyone listening right now to miss a couple of things. Sometimes people watching someone like you on the outside, they're thinking, oh, it was easy. It just sounded easy. And the way you just made that sound to me sounded easy. However, I happen to know a lot more based upon your writing. Can you talk to us a little bit about and so the listeners understand you were in private equity, which is a completely different animal, guys, than being in operations. I mean, it is. And Psycho has private equity. Nothing against you, James, and I know you aren't this way typically. And I've done a few different deals with private equity. They want to ring every last penny out. It is cutthroat. It is definitely not typical environments where women are elevated, are encouraged and supported. It is a very difficult environment based on numbers exclusively. That's been my experience. You were sitting in a private equity seat. You were on the board, I believe I was for this company. And you decided to step down and take over as CEO in a not glamorous, not attractive situation that was not near your home, not conducive to the situation you and your family had created.
It wasn't like it was some fancy fashion brand in the Hampton. You know what I mean? It was the opposite. And yeah, it was hard. Like, believe me, it was not an easy decision, Right? It's not like I'm some monk. I have an ego too, right? And I was like Wow. I built my whole life from being this public school kid from Long Island. Like, my parents really wanted me to not struggle as much in this country as they did. And they were horrified. My mom was like, what are you doing? And I kept saying to my mom, I'm like, no, these women are kind of like you. Like, what's the point of knowing how to do all this stuff that I can now do if I can't be helpful to women like you?
What was it about your mother's behaviors, traits, characteristics that was similar to these women?
I think that a lot of women generally. Okay, generally, but. And then also I think my mom, you know, she had a language barrier. And the women that I served at Ashley were predominantly black women and like plus size black women and moderate income. So a lot of X is against them. I think also, like my very well educated, privileged wife who's a white woman, you know, I remember her when she took time off after having our children and was thinking about getting back into the workforce, saying to me, I don't think anyone's going to want me anymore. And me looking at her and saying, well, they're idiots. So the common refrain about all this. And I grew up a lot with this at the kitchen table with my mom, I hate systems or people that make people and particularly women like this feel small. I hate it. And I grew up like that. I'm like, mom, like, it's not you, like, it's just. You're awesome. It's the way things are configured or you know, mental models and like, don't listen to them. It's easier said than done. Look, I get it, right? And so it gets into your head. So I grew up that way. So yeah, these women that I was like, these women are made to feel small a lot. And they shouldn't feel small because what they're doing, frankly, sometimes it's heroic what they're able to pull off. A lot of the game is rigged against them. And anyway, that's how I am. Like I was, I'm my mother's son. And so even though she wanted me to not notice all that stuff, like, I'm acutely sensitive. I'm a sensitive guy, right? I'm a, I'm a musician, right? So like really I am. And so like I'm a musician that knows how to make money. So I saw that it was at a time in my life when my dad was dying, you know, and I'm 42, 43 at the time. I'm a father now of three kids. I've got two daughters, son, you sort of. That Valjean moment. I'm like, am I going to look the other way? Like, that would be ridiculous. And I had a hard time, so. But I wasn't a complete idiot. I said, I'm going to resign and resign from my life for just six months. That was the plan. And then I thought for sure someone would come in with a little bit of money, save the stores, and then I'd come home. And during those six months, I learned a lot about reality and a reminder about also who I was. No one came. Like, two people come. Some young people that helped me, but no one came. And it's amazing how some friends, you lose them when you don't have the fancy business card. And I just looked at everybody. I was like, this sucks. And I was lonely. Yeah, it was not easy. I had a lot of moments alone at 2am in a hotel in New Jersey, just like, pounding my head against the wall and saying, you're so stupid, James. Yeah, this was not like a hero moment. I'm like, what the heck are you thinking? Like, this is. But I couldn't look the other way. Like, I just. And what saved me, frankly, was that when I was visiting all the stores across the country, Remember when you read the business had no WI fi, so they didn't know what I look like. So you have to picture me coming in this, like, Korean American dude that's wearing, like, pleated khakis. No fashion sense. I hadn't discovered fashion denim yet. Like, I didn't know it was a thing. So I'm wearing, like, pleated khakis, my blue blazer with the gold buttons, you know, the private equity uniform, you know, I'm talking about. Right. Like, to sort of, hey, what's. What's up?
And it's a dressier Blockbuster uniform.
Totally. I was probably better off wearing a Blockbuster uniform. Like, it was that. And you have to picture me now going around America and predominantly black neighborhoods, and they're like, you're James You. And I'm like, totally like me. And the greeting that I got was incredibly generous. And they were like, you know, you. And years later, I asked them, I said, you know, like, a lot of women get burned a lot. And I think that it's fair to say there are a lot of big promises sometimes to black women and no action. I don't talk a lot. I just do stuff. I'm like. I say it once, and I'm like, I said it. We're going to do it. But they said later it was nice. They were like, you know, despite what you look like, and you didn't talk a lot, but we could feel your heart the minute you walked into that store. Like, your heart, like you have. You radiate, you know, In Korean, it's like, in English, it's goodwill. And they would say, james, you have a lot of soul. Like, we can feel it. And I was like, you know what? I do have that. I realized that for a lot of my private equity life and sort of my, like, macho golf life, whatever, like, I guess for guys, sometimes it's not cool to care about things. I'm like, that's stupid. I don't want to live like that. So I said, yeah, I do have a lot of soul. I do care a lot, and I know how to do all this other crap too. And it was that way. And I basically sang an anthem to a lot of the women in the tone of it was like, red Helicopter, in a lot of ways is an anthem. And I'm singing, and I'm a big Bruce Springsteen fan. So effectively what I was singing was, it's in Born to Run, he sings, you know, will you walk with me out on a wire? Because, baby, I'm just a scared and lonely rider which I was. But I got to know how it feels. I want to know if love is wild, girl I want to know is your love real? And I was basically saying it to them. I'm like, I know I am everything you don't need But I'm the only one who came. I'm on this bike or helicopter. Do you want to go? And the whole world laughed at me, but they didn't laugh at me. And they came and they were like, we're in. And so it was just me and them against the world. And it was lonely, but it was awesome. And so that feeling of friendship and, like, not wanting to disappoint them, it gave me superhuman strength. Like, I was just like, you're not gonna lose. It just won't happen. But it was hard. Like, it was physically taxing. I was away from my family. I had bouts of, like, real loneliness and self doubt. And every time I had self doubt, I thought about what I promised them, which was ride or die. I thought about my mother, and I also thought about, you know, my wife would encourage me and say, you know, the man that I married, he sees things through and he's a fighter. And so I fought. And anyway, that's what happened. So that's a long answer to your Question. It was not an easy time period. You know, there was a lot of loss, too. And so. But that's life. You know, it's not toxic optimism. There's a lot of loss and sadness in life, and it makes those moments of joy that much better.
What was the turning point or where did you bring it together that you were able to say, okay, this is what's going to change things here?
It was a lot of little things every day where it was very interpersonal. And, like, again, I don't talk a lot, live a certain way. And so they were watching everything. Is this man going to come down here every freaking Monday at 6 in the morning from Boston? And it was the real turning point, when I think about this, was at my dad's wake. So it was two years in to this crazy ride, and I was so tired. And I had a week in the book. It's the Bridge, it's Goodwill. I had a week that I was really tested. Like, so my dad died after, like, 15 years of Parkinson's, and my daughter almost died in a camp accident same week. And I'm sitting there, a macho guy, like, telling my assistant, don't tell anyone. I don't want to be a burden to anybody. And so, like, I basically said to her to lie, basically tell him I'm on vacation. And so I'm looking upstairs a bit, I'm like, why all this? Like, you know, like, this is ridiculous. And at my dad's wake to. I don't want to spoil the book, but, like, at my dad's wake, I thought the wake would be mostly like, pediatricians. It's my dad's scene. And my assistant basically overruled my thing. And she brought everyone from the home office. They all came. And our home office was like the United Colors of Benetton. It was, like, ridiculous. I was holding together. But what I really lost it was that the frontline workers from the stores and carpool to come to my dad's wake. And I'll never forget it. And they all met my mother. And I remember watching them and, like, one of them saying, you know, Mrs. Rhee, we think you did a pretty good job with your son. And that was it. And then they came up to me and they, you know, they were like, oh, you know, James, you didn't tell anyone. Why didn't you tell anyone? And one of them held my hand and said, you know, like, you didn't think we'd find out and be here for you? And I cried. Like, I mean, so, like, I was 44 at the time. So I'm sobbing in front of, like, I'm, quote, CEO, chairman, like, tough. I just sobbed. And, like, all my parents, friends were there. And so in that moment of tragedy, I really. At that moment, I was like, this moment is success. And so to this day, like, almost 10 years later, there are very few things that bother me. A lot of my little weird insecurities or ego stuff, they're just gone. I'm like, it's not important. Like, it's just not important. And so the armor went fully off at that point. And it's like being naked, it's like, this is it. And I think that gift, like, they gave me that gift. It's hard to find friends in your 40s that really like you because you make them laugh, you know, and everyone's so caught up in, what can you do for me. And I don't live a transactional life. I never have. Like, I just don't live like that. It throws people off at times because of, like, my bio is like, who the heck's this guy? I hate that bio. Honestly, like, I really don't care. That's where I am in my life. I just sort of live like a Forrest Gump life a little bit. And I do things that make people, I hope, happier or better. And I generally find that if you do that, you do get rewarded, both spiritually but also financially. And you do, particularly now. You know, people are so lonely, and it's so people are so angry. And I wrote Red Helicopter in some ways to make people less angry and teach them some things that maybe they don't know about so that they can be less angry. They'll say, ah, that's why I feel this way. Or the financial systems work that way. Got it. And so I feel like the more, you know, maybe people will be less angry. And that's a good start to just have a nice conversation. My answers are really long. Are they too long?
No. I love that question. No, not at all. It's so interesting. All right. I feel like a lot of people that are listening are in leadership positions aspiring to be leaders, Right? And one of the things, especially, I know having been a younger leader, you think it has to be that certain way. It has to be the blue jacket with the gold buttons, and you have to be tough and you have to be disciplined, and you have to cut people and businesses cutthroat. And, you know, James, the majority of people believe that. How do you speak to them? Or what can you teach them? To get them to understand that giving more, being more vulnerable is actually the solution not only to happiness, but to bottom line success.
Yeah. So the reason why the subtitle is about kindness. I go to great lengths defining really what kindness is. And I always ask people to think about their favorite teacher or coach or parent or aunt or uncle, that it's that person in your life that holds you accountable to be your best self. And that when you're not, you have feelings of like, ugh, I disappointed that person. And they always say to you, no, you didn't disappoint me. Why are you disappointing yourself? That's a great leader. And so that person that inspires that out of you, think about it. They're not angry, they're not cutting, they're not screaming, they're growing. They're like, investing in you. And they have high hopes. They're generally very calm and they sort of give you, like, the look when you kind of screw up and you're like, ugh, I screwed up. And then they give you the next look, which is like, still believe in you. You know, are you going to learn from it? So that's what I believe kindness is. You're investing in someone's agency. And so that type of person, intuitively we know that person is competent, right? Very sure of themselves. They're not trying to live vicariously through you. They're confident in their own self, that they're comfortable you having your own life. It's very generous. And so leaders like that share half their sandwich, share the credit, share the press, share the attention. They're very confident. They know they look better when you look better. They're like, there's a lot to give to go around. They don't act like scarcity people. They're very abundant. And so when you have that confidence, you're, I think, confident enough to walk around naked too and say, yeah, I suck at this. I don't know this. And when I look back, that first speech I gave to the women at Ashley Stewart, I said to them, I was like, I'm probably the least qualified person to run this company. I'm none of the things you need. Female fashionable retail executive, all these things. But I'm the only one who showed up. I'm the only one who cared enough to be here. And so when I said that, people who mistook that for lack of confidence were wrong. I think that's real confidence. Like, I know what I'm not. I don't have to pretend like, I'm like, I don't have time for it anymore. This is who I am. I don't know if you got to the part where I was courting my wife when I first met her, I was like, I married way over my head, right? And I remember saying, girls, like, I know you know, and there are lots of other guys. And like, I'm. No one's offering me a modeling contract. I'm poor. I've got one hundred and something thousand dollars of debt. My last job was teaching high school. There was a race part of it, too. Like, I'm Korean, she's Caucasian. She's like a North Carolina white girl. I remember saying all that to her. I was like, I know that I'm not any of those things, but I was like, if you're willing to invest the time that I have, really some good qualities that I think that might amuse you, that might be good over the long term. And I remember her looking at me and saying, is that. That's it? That's the best pickup? That's your line. I'm like, but it's the truth. And isn't that worth something? The truth? And so that's what Red Helicopter is, too. It's truthful. It's encouraging people to be honest. And I think that some people, yeah, they may penalize you for that. And the answer to that is, like, then you're hanging around with the wrong people.
Yes.
Amen to that. Oh, my gosh, that is so good. I want to bring up James, so something that I know you won't bring up, but I think it's so incredible and it's important to talk about because this whole idea of giving back, including sharing, being this vulnerable leader, and that it does deliver success. I want to talk a little bit about how Red Helicopter now isn't going to just be a book. Red Helicopter is going to have a run of success beyond what people are used to seeing with the book.
It's a branded world. It's a philosophy. So, like, I teach it at these schools. So I know how to teach how to live like this, to fly like a helicopter, to be agile. So I'm teaching law, money, cognitive science, wellness, like, in one spoonful. Like, you know what I mean? Like, it's like, eat it and then you eat all of it at the same time. It's like, oh, yeah, that's cool. So that's agency over time, you'll see me teach it more on scale to young people and leaders. Anyone leads their life. If you want to lead your life. I'm for you, you know. But if you don't want to lead your life and you want to sort of ride in someone else's life, call me when you want to have agency and I'll be there for you. So that's number one. Number two, yeah, there'll be a couple more books, kids book. But I'll say it. I think the fun part, the other, it's a community and a brand that symbolizes this way of living and trust, which will be in short supply. Do I think there's gonna be a feature length movie? Yeah, I do. And it's gonna be ridiculous because the story doesn't even have to be made up. And I'm gonna say something funny, which I've never said publicly. It's just my inside voice. I've had conversations and, you know, I have like an agent in Hollywood, which I'm like the least likely guy to have an agent in Hollywood. It's ridiculous. I don't even know what to do with them. But I said I want this story just like the book, to be honest. Really just like a flat story. Because it's so ridiculous that you don't have to like exaggerate it or anything. The only thing I want is that we talked a little bit, that the protagonists are all women. There's three women of three different races. And I'm like the bumbling idiot that these women in my life made me better. They made me think and like behave better. But the small parts that I think that maybe if this gets made that I'm going to be in. I want whoever plays me the only requirement. I want him to be shredded. I don't mean fit. I mean shredded.
My gosh, I can't take it.
That's it, you know, Like, I don't care. Like, like, yeah, I should care a little bit, but maybe he should look a little bit like me. But like, what's more important is just shred it.
You gotta have it. You're gonna have to write that into your contract.
Yeah.
And like, so there has to be one scene, like when in a boardroom or something when he's stressed and like the financial model's not balancing and like, like tight shirt. I'm like, wow, James. Shredded. I'm not shredded. For those of you who are listening, like, it's. I'm not like, I'm easing into middle age pretty quickly. So, yeah, I'm not that. Anyway, I think that would be cool, right? Like, wow, that guy's Shrek.
Meet a different guest each week.
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I asked you to try to find your passion but the idea of a movie about the concept of red helicopter featuring and focusing on three women from different races, different backgrounds but all that were elevating and encouraging you and examples for you is such a beautiful thing. I will be at that movie theater.
You'Ll be at the premiere, I will.
Be there and I will be cheering on whoever plays you. But more importantly, your mother, these women that you worked with and your wife and the impact that they had. And it's, that's a beautiful, beautiful story.
Because my whole career, if you think about it, is that my job even in investing is to find value where other people's don't see value. And I think it's fair to say that, you know, my mother, the women I worked with, my wife, all women. The way things are sort of configured, the true value that women create in our society, it's not measured. It's not like motherhood is not a measured economic GDP input. All the women in my public school in Long Island, I had the best teachers because many of them were women. They had a harder time getting a job not teaching. In the 70s and 80s they were more limited opportunities. So I had like hyper smart public school teachers. I mean it's like, and look at all around the world right now you have declining birth rates in certain pockets of. Because it's not possible. Like a lot of women are saying, are you kidding me? Like you want me to do this and that? And like anyway, so one of the most important things I did at Ashley Stewart was, you know, I ran that company much more like it was like a country actually. So one of the things I noticed when I was CEO, you may think I was like, you know, obviously I'm a quant guy, I'm looking all the numbers. But I was looking at like what's the problem here? And we didn't have a lot of new families being formed. There were very few babies because a lot of the women that were Working at the company, they felt stressed about the viability of the company, the leave policies, the general environment. They didn't feel comfortable that maybe if they got pregnant or had to take leave that they would not get their job back. There are many things to think about. And I said, oh, and we were not attracting, like, more youthful women because they thought the company was not viable or relevant anymore. And so I said, well, I think one of the goals, if we do this right, to encourage family formation, it will lead to many really good things for us to change in this company. And so we started to have lots of kids. We had tons of births. And I always used to sort of just smile. I'm like, when, you know, Gina would always plan these surprise baby showers, which ended up not being surprise anymore because they were like hyper planned. I was like, this is really successful. And to do what we did, it required adjusting 20, 25 things just a little bit, right? To really listen to the moms and say, hey, like, they felt more confident in their company and their relationship in the company. And they used to bring in their babies all the time, which modern day moms don't do as much anymore. I think old days people did. And you show off your kid. We had tons of babies, like, strolling around the office and I just remember sitting there, like, looking around and feeling very content. Like, I'm saying, this is pretty freaking cool. And some people who may be listening may say, oh, that's, you know, oh, that's not driving profit. Of course it's driving, quote profit. We had very little turnover, you know, and like, people really wanted to work there and they gave us their best. And of course it was, quote, profitable.
I mean, the customers feel that, like you said, there's a lack of turnover, which is such a costly factor in any business, as well as they're the ones out there recruiting and advertising for you. Because everyone's talking about how much they love the company.
Totally. It's so intuitive, right? It's like radical common sense. And. And that's why that red helicopter story, for me, it's like, he doesn't have lunch. Give him some food. It's like that old Aesop's Fables. It's like one of my favorite stories. There's a kid drowning in a river, and there's an old man walking by and is like scolding the kid. He's like, you shouldn't have been walking close to the riverbank. And the kid in his last breath says, you're right, sir, but would you mind Saving me first and then you can scold me. And so it's like stuff like this. It's like we do a good job, I think increasingly just like, we like to yell at people and point out all the things that they've done wrong. And like, even this book, you know, in the beginning, people wanted me to write a business book because that bio that you read, like, concretized, like, they're like, you're going to write a business book on, like, how to make a lot of money and transform companies and build brands. I'm like, yeah, I could, but I'd rather not write that book. I also would rather not write a book that says, here are all the reasons why you suck and here are the five things you can do to not suck. I was like, I don't want to do that either. And so the tone of the book and I think the way I try to live my life is like, you know, you're doing pretty good. Trust your intuition more. I got your back. And by the way, after you feel like you're in a good place, here are three or four things that, yeah, you should probably know how to do. You probably were never taught it in school and no one else was, so you don't have to pretend with me. Like, it's okay. Like, so I didn't know it either. And so here's what I learned. Maybe this will help you sort of, like, feel better and make feel more control of your life. And that's the tone of the book, but it's actually the tone of the way that I live my life and. Or lead a company or anything like that. It's. I think people are made to feel bad and I don't know why we do that. And I don't think good leaders do that. I really don't.
Oh, I'm so with you, James. Where can everyone find Red Helicopter and where can they find you?
So I'm social media. Not good. So there's RedHelicopter.com is the website for the book. And there's also original music on there. And the music is really cool because it conveys the whole book in music form. So I want to do a rock opera. That's sort of my big project. And then they can find me on LinkedIn. And then I am James Re on my really lame Instagram and I'm really bad at it. So I'm trying to start doing it and I'm really bad. And that's really kind of it, I think. Like, you know, I love to Hear people's feedback on the book. And I'm asking people to sort of share if they feel comfortable at some point. Like, what is your red helicopter story? Like, what is that for you, that North Star where you were kind of like, at your best? It's that person. And I can sort of see down the road, like, I want to, like, create more short films about very quiet leaders and heroes. And my audience skews. Like, it's like 60, 70% women. That makes sense to me. Right? And it's a lot of younger people who are really scared about the world. And it's a lot of, like, I find mother, son, mother, daughter combos, that it's a lot of moms who are a little bit worried about their sons, you know, because they have a really good relationship with their sons. Their sons are, like, emotionally available and fun and laugh. And then the moms and the sons are worried that, hey, when I go out and quote the real world, does that all go away? And so I get that a lot in my inbox, like, that duo. And the book is a lot about me and my mom. So, like, that makes sense to me too.
Well, everyone get the red helicopter. It's an incredible book. It's a movement. This is changing lives everywhere. If you are someone who wants to learn to lead, who wants to lead their life and wants to have happiness and success and find a way doing it with kindness, get red helicopter now. James, I am sorry. Such a super fan of yours. I am so proud of the work that you're doing. I'm so grateful for you being here. Please continue to keep changing the world and let us know any way we can support you.
I will have gotten a lot better asking for help. I definitely will. So help me with my Instagram. It sucks.
I'm here for it. We're here for you guys. Until next week, Go get the red helicopter. You know that we've got it right here, and I can't wait to hear what you think of it. Until next week. Keep creating your confidence. We'll see you then. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably, something will happen. No one succeeds alone.
You don't stop and look around once in a while. You could miss it.
Come on this journey with me.
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