The Transformative Power of Embracing Agency and Purpose to Thrive in Life and Business
James Rhee, acclaimed CEO and Founder of red helicopter, explores the key elements of his operating system and reveals how individuals and organizations can harness this mental model to lead with intuition, steer their own path, and thrive amid complexity.
James Rhee is a former high school teacher and Harvard Law graduate who became a private equity investor and a highly decorated but 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, 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.
James describes red helicopter as an operating system that creates, measures, and amplifies a sustainable balance of life, money, and joy in the life of business and the business of life. Grounded in behavioral science and philosophy, its methodologies have been battle-tested in boardrooms and classrooms for nearly three decades. His TED Talk and Dare to Lead interview with Brené Brown have captured the imagination of millions. James runs a media-education platform, also called red helicopter, and is working on related film, music, and television projects. He holds teaching positions at MIT Sloan School of Management and Duke Law School, as well as Howard University, where he earned a historic appointment as the Johnson Chair of Entrepreneurship and Professor of Entrepreneurship.
The Continuum sat down with James to talk about his career and his operating system.
You started your career as a classroom teacher. What made you decide to go into teaching initially?
I've had a lot of different careers, but I think by nature, I am a teacher. It’s not always by job title, but it’s who I am. I am a teacher. Teachers are investors in people, and I’ve always been an investor in people. At different phases of my life, I picked up different ways to invest in people, whether that’s time, education, money, emotional investment, or creating jobs and companies.
Like others, I was trying to decide what to do next after college. I was a public school kid, the son of immigrants, and I was about to graduate from Harvard. I think Harvard was the first brand I was ever associated with, and I had mixed feelings about it. It holds a lot of weight, so where do you go from there at 22? A lot of my friends got risk intolerant because of the Harvard brand and looked for paths that would seem as important. I went in a different direction.
I took a job at a school no one had heard of, where kids were struggling. I think I made $12,600 a year teaching American and world history. I also taught a class in American culture and created a new class called Money and Investing. I didn’t know much about money then, but my coursework in college centered around human behavior, which included economics, so I designed a class about how to live your life rather than the theory of economics. Even then, I realized that kids needed to learn that.
It was a really great experience. I was teaching them about history and money in the classroom, coaching them on the football field, and nursing their boo-boos at night in the dorm. It was a holistic investment in my students. Of course, I learned a lot too. If you’re not learning, you’re not a very good teacher.
Your next move was to return to Harvard for law school, but when you graduated, you ended up working in finance instead. How did that happen?
I summered for a couple of law firms and knew pretty quickly that I didn’t want to practice law. As I said, I’m an investor in other people's agency, and I like helping people make informed decisions that are best for them. I had originally assumed I’d become a public defender. I like giving counsel, but I realized that in my professional experience, I wanted to be the actual principal decisionmaker rather than giving “advice.”
I also realized early on that when you’re managing and controlling the money, you’re more likely to have the ability to influence decisions and create organizations. The lawyers aren't managing the money; they're giving advice to the people who are. So, I decided to go toward finance instead. I also had a ton of debt from law school, and while making money had never been my top priority, it didn’t feel good to be drowning in debt.
Of course, I’ll never regret going to law school. Ultimately, law governs money. Plus, I met my wife there.
One of your early roles was in a private equity firm in Boston. We talk a lot about private equity and its role in brands these days, but few people outside of finance knew about it at that point. What were you working on?
Private equity was definitely a younger industry then. My firm was managing about $3.5 billion in capital. We took a majority interest in a number of companies, primarily consumer, retail, and healthcare service companies. This wasn’t a hedge fund. We weren’t trading securities on Bloomberg. We had to really understand the companies and the industries so we could help them grow.
One of the things I worked on was spinning off Meow Mix from Ralston Purina. I learned a lot about consumer behavior on this project. As we all know, consumer behavior is half rational and half irrational, especially when it comes to why people have loyalty and emotional connectivity to certain brands. We also had to build a company from scratch in less than four months.
I always thought about Meow Mix as if it were Wendy’s. It’s not McDonald’s; it’s not Burger King. Wendy's is third, and it has square patties, right? It's a little bit quirky and has a little bit of an attitude. It's not trying to be one or two. It’s happy to be the freckle-faced girl with red hair. People relate to that.
That’s how we approached Meow Mix. We didn't invent the jingle, but we brought it back. I’ve studied the neuroscience of music. Research has shown we remember things in stories and music. That’s how we’re wired, so we brought back the jingle.
“If you think about life, part of thriving is being able to fly in six different directions, to land, and maybe to cut yourself some slack and not fly as high or as fast but to pick your spots.”
One of the other brands you worked with in your private equity role was Ashley Stewart, the clothing store. You went on to be their CEO and really reinvent the brand. Tell us about that.
Ashley Stewart is a plus-size clothing business based chiefly in Black neighborhoods. I got involved in 2013 when the company was weeks away from liquidation, only three years removed from a bankruptcy filing, but I saw something more.
Think about this: the target audience was plus-size, Black women with moderate incomes. The design of our systems have not made their lives easy. I felt like I could relate because I grew up surrounded by immigrant Korean women, like my mom, who struggled communicating in their second language. I didn’t like that my mom was made to feel small. I remembered what it was like for my mom to go to the Korean grocery store and how it was a place where she felt confident. I saw that Ashley Stewart could be that place for its consumers.
We designed a world called Ashley's story, which was really the capital P product—the brand. The clothes were just a manifestation of that ethos, right? To sell that image, the clothes had to be fashionable, sexy, and confident. I know nothing about fashion, but I know the formulas and organizational theory, and in some ways, I built a media brand.
Within a few years, this twice-bankrupt “apparel” business was hosting massive concerts in Brooklyn, and we were partnering with voting organizations to register women to vote when they were being told they couldn't.
I was supposed to stay for six months, but no one else showed up. In fact, the entire world turned its back. So, I took on the role of the CEO, teamed up with my primarily Black female employees, and proceeded to shock the world. Years later, so many of them came to my dad’s funeral, and I think my mom finally understood that I had built something for love.
Let’s talk about red helicopter. It’s a book and a media-education platform, but you refer to it as an operating system for individuals and organizations. Can you explain what that means and what’s behind the name?
The book is structured around life, money, and joy. It’s about how to thrive, whether you’re an organization or a person. Everyone’s a leader because you’re leading your own life, right?
The mental model I have people do is to look at themselves as a helicopter. We are taught that the vision of success is a jet plane because it flies high and fast. I don’t think that’s right. I teach people how to be a helicopter. They’re much more difficult to fly. They’re highly inefficient. They crash more. They don’t fly as high and are not as fast, but they are very agile. They can fly in six different directions, land anywhere, and have vertical lift.
If you think about life, part of thriving is being able to fly in six different directions, to land, and maybe to cut yourself some slack and not fly as high or as fast but to pick your spots.
This informs a certain mental model of leadership, where I encourage people to fly their own helicopter rather than be a passenger in someone else’s plane. Helicopters can’t carry a lot of people. It’s a really good symbol for agency, right?
Once that mental model is there, what I’m teaching is basically how to implement the latest in cognitive science and positive psychology, woven into the principles of law and money, into your life or your business.
“We need to put empathy back into relationships and brands. If you’re not working for and measuring that intangible goodwill feeling, you're not a very good brand manager.”
When you were the CEO of Ashley Stewart, you counted babies. What was that about?
One thing I like to point out as a finance expert is that accounting is made up. It’s not some commandment from God; it's not physics; it's a convention, a measurement. If you don't know that, you are being held captive by someone else's measurements of success. I want to help show people what’s not measured.
When I first got there, women weren’t starting families. It makes intuitive sense, right? People were scared for their jobs. One of our main goals was to create a company where people felt secure enough to also live their lives. I know that corporate America’s rigid hierarchy and vertical world are not conducive to families. As a company, if you want women to have families, you have to change like 20 different things at the same time. It forces you to ask why you’re clinging to certain rules and question whether they make intuitive sense.
Once you change those policies, you have to measure success in ways that are not part of typical accounting. So, I counted babies.
One of the things you say we don’t measure often enough is goodwill. Why do you think that is so important?
We’re at a once-in-a-generation inflection point on systems right now. The pace of change is like nothing we’ve seen before, and leaders are dealing with so many big issues. That’s why we’re seeing so many high-level resignations right now. Everyone's burning out. That’s why I talk so much about goodwill and why I did a TED talk on it.
I think goodwill is what we’re missing most in our society right now. We need to put empathy back into relationships and brands. If you’re not working for and measuring that intangible goodwill feeling, you're not a very good brand manager.
I’ve looked at many investments in brands and start-ups in the last 25 years or so where they tried to buy loyalty with venture capital instead of earning it through goodwill. Most all are gone; they never made any money because they didn’t connect with consumers.
When I was at Ashley Stewart, I understood that a lot of our brand equity was clearly not in the financial statements.
This book itself was very personal for you. You’ve described it both as a piece of literature and a piece of music. Can you explain?
It's not an ordinary business book—it's written like a piece of literature. It's really a love story for my parents, my wife, and the women at Ashley Stewart. These women embraced me when many people were making fun of what I was doing. They didn't flinch, and I'm very grateful in many ways.
I think we worship a lot of false idols, and the way I was writing the book is designed to help people understand they’re better than they think they are. I want readers to stop giving up their agency to all those around them and start trusting their own intuition.
The book is also written as a piece of music. Musicality is the way my brain works. I have a lot of professional musicians in my family. Sometimes, I wish I’d had the talent and courage to become a professional musician. I play violin and sing okay, but more importantly, the way I receive people, sounds, emotions, and brands is very much like a musician. I associate people and brands with different types of music, and songs help me memorize things.
I’ve actually collaborated with a professional musician to write a piece of music that corresponds to the story in the book. When you listen to it, you can hear the unofficial national anthem of Korea, which is about what it means to be Korean. So that's my mother and my father's story. That’s the cello. And then there’s the violin, which is me. Then you hear the saxophone and Amazing Grace, which represents the friendship of the Black women who helped me mourn the deaths of both my parents.
It keeps going like that, telling the story of the book musically. I had music in my head as I wrote the book, and this is what the book sounds like. (You can listen to James’s music on the red helicopter website).
“I want readers to stop giving up their agency to all those around them and start trusting their own intuition.”
The book was published earlier this year, and you’ve been doing a lot of speaking around it. What else are you working on?
I've used this operating system my whole life—as a teacher, in private equity, and as a CEO. The red helicopter is itself a brand. It's not just a book; it's a branded way of being, of creating real value in your personal and professional lives.
The book is doing great. Per USA Today, it opened up as the number one non-fiction book in the United States. It’s being translated into multiple languages already. I’m teaching about the operating system in academic settings like Howard, MIT, and Duke. And I’m working with the CEOs of some of the world's most forward-thinking companies right now. I also still invest in some companies, whether investing money, expertise, or my rolodex.
There are other ways to grow the brand. There’s the media-education platform, and I’m working on related film, music, and television projects. I don't believe in doing a lot of paid acquisition in marketing. Most of the things I'm involved with are very organic and very sticky. And I have the benefit of time. I’m not in a rush.
I like to think that red helicopter is a song for humanity. I’m singing in a certain key and just asking the world, “What do you think?” Because there is a better way.
November 12, 2024
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