Red helicopter

Red helicopter Plot Summary

Introduction

Imagine standing in a failing company's cafeteria, facing employees who have weathered years of mismanagement and broken promises. The business is weeks away from its second bankruptcy in three years. As the newly appointed CEO—someone with no experience in this industry—what would you say? When James Rhee found himself in exactly this position at plus-size retailer Ashley Stewart, he made a surprising declaration: "I think if we can center kindness and math in this company, we can get out of this mess together." The room fell silent. In corporate America, "kindness" was never mentioned—it suggested weakness, vulnerability. Yet something about this approach resonated deeply with the employees who had weathered so many storms. What makes this journey remarkable isn't just that an unlikely leader saved a failing company against impossible odds. It's how he did it—by challenging fundamental assumptions about business, leadership, and value. Through integrating seemingly opposite forces—kindness and mathematical precision—he created a model that generated both financial returns and human flourishing. This approach reveals that sometimes our greatest strengths come from embracing the very parts of ourselves that seem least relevant to conventional success. By reconnecting with childhood wisdom and immigrant values that the corporate world had taught him to suppress, he discovered a more authentic and effective way to lead that transformed not just a business but countless lives, including his own.

Chapter 1: The Unlikely CEO: A Korean American in Ashley Stewart's World

Imagine walking into a company headquarters on your first day as CEO, knowing you're completely mismatched for the role. This was James Rhee's reality when he stepped into Ashley Stewart, a fashion retailer serving plus-size Black women. As a Korean American man with no fashion experience, he couldn't have been more different from the company's customer base. The situation was dire - the company was weeks away from its second bankruptcy in three years, with no Wi-Fi, crumbling infrastructure, and demoralized employees. During his first town hall meeting in that dreary cafeteria with its industrial-size food warmer, Rhee made a surprising declaration. Instead of presenting a complex turnaround strategy, he simply stated: "I think if we can center kindness and math in this company, we can get out of this mess together." The room fell silent. In corporate landscapes, "kindness" was never mentioned - it suggested weakness, vulnerability. Yet something about this approach resonated deeply with the employees who had weathered years of failed leadership. What Rhee recognized was that Ashley Stewart wasn't merely selling clothes. The stores functioned as community centers where plus-size Black women found respect, confidence, and belonging. Store managers like Chary and Shelley knew their customers' families, celebrated their victories, and supported them through hardships. They created safe spaces where women who were often marginalized in society could feel seen and valued. This human connection was the company's true asset - one that conventional financial metrics completely missed. As Rhee immersed himself in the business, visiting stores across the country, he witnessed firsthand how these neighborhood stores served as sanctuaries. He saw the relaxation in customers' shoulders, their confident voices, and hearty laughs when they entered. It reminded him of his immigrant mother's transformation whenever she visited a Korean grocery store - the rare place where she felt completely at home and in charge, free from the anxiety of navigating a foreign culture in a second language. This realization triggered a childhood memory that would become central to Rhee's leadership philosophy. When he was five, a classmate's father had given him a toy red helicopter as thanks for sharing his lunch with his friend, who often came to school without food. This simple act of kindness had been recognized and celebrated, creating what Rhee describes as "a warm, good ache" in his chest. The red helicopter became a powerful symbol of how kindness could be made tangible and how small acts of generosity create lasting connections. What makes Rhee's story remarkable isn't just that he saved a failing company against impossible odds. It's how he did it - by challenging fundamental assumptions about business, leadership, and value. He showed that kindness isn't soft or impractical but rather a powerful force that, when combined with mathematical precision, can transform organizations and lives. His journey reveals that sometimes our greatest strengths come from embracing the very parts of ourselves that seem least relevant to conventional success.

Chapter 2: Balance Sheet Thinking: Redefining Assets and Liabilities

When James Rhee realized Ashley Stewart was heading toward bankruptcy, he gathered everyone in the cafeteria to explain what was coming. Rather than sending impersonal legal notices, he stood before his colleagues and read the Worker Adjustment and Retraining Notification Act (WARN Act) himself, looking them in the eyes as he delivered the news that their jobs were at risk. The room fell silent with the weight of reality. But instead of leaving them in fear, Rhee took the time to educate them about bankruptcy law, explaining the system's pecking order where secured lenders get paid first, followed by unsecured creditors, with employees often left with nothing. "Does that make sense?" he asked. "Do you now see why the clothing vendors insisted on cash up front, and why some of those who didn't were angry and anxious enough that I felt compelled to hire a police officer to sit downstairs in the lobby?" The body language in the room screamed that this didn't seem fair. But Rhee was honest - that's just how the system works. Rather than hiding behind corporate jargon or legal shields, he created space for his colleagues to understand the reality they faced together. After emerging from bankruptcy, Rhee gathered his team in the cafeteria and played "Here Comes the Sun" by The Beatles. No speeches, just music that spoke of rebirth after a long winter. This simple gesture set the tone for the company's transformation - one that would challenge conventional business thinking at every turn. Rhee knew that to succeed, they needed to reimagine how they measured value and defined success. He began by teaching everyone the fundamentals of business through the metaphor of a lemonade stand. "What's the product?" he asked. The answers came back: "Safety, self-confidence, friendship." "Who's responsible for this company's results?" "We all are," they replied. "And how are we going to do this?" "Kindness and math!" This wasn't corporate jargon but a shared language that everyone could understand, connecting childhood wisdom with adult responsibility. Rhee explained that conventional accounting only captures what can be precisely measured in dollars. The T-account - the fundamental framework of balance sheets - divides the world into assets (things that create future value) and liabilities (obligations you must repay). But this system misses crucial intangible assets like trust, wellness, or connectedness. At Ashley Stewart, they would track these invisible assets by adapting internal behavioral standards more consistent with a child's lemonade stand than a Wall Street boardroom. This approach transformed how they viewed inventory. Previously, the company had invested heavily in basic black and white camisoles, storing them in back rooms for months. On paper, these were "assets," but in reality, they tied up cash and couldn't be sold. Rhee mentally recategorized them as "liabilities" and created steep promotions to convert them into cash, which was then invested in a new e-commerce platform - a true long-term asset. Through this balance sheet thinking, Rhee demonstrated that business success doesn't require choosing between profitability and humanity. By recognizing the full spectrum of assets - including those that conventional accounting ignores - Ashley Stewart created sustainable value while honoring the dignity of everyone in its ecosystem.

Chapter 3: Kindness Systems: Building Mathematical Precision into Compassion

On a cold winter day, James Rhee received devastating news: Ashley Stewart's workers' compensation claims had reached alarming levels. Store employees were getting injured at rates far exceeding industry averages. Most companies would view this as an inevitable cost of doing business, but Rhee saw it differently. "Imagine you're running a lemonade stand when one of your colleagues slips on an ice cube that you dropped," he told his team. "Whose fault is it? Right—it's yours." He made himself personally accountable for monitoring every incident, insisting he be among the first notified whenever someone got hurt. This wasn't micromanagement but a fundamental shift in perspective. Rather than treating workplace injuries as random events, Rhee viewed them as symptoms of broken processes that could be fixed. He implemented new safety protocols, invested in proper equipment, and most importantly, created a culture where everyone felt responsible for each other's wellbeing. Store managers enthusiastically embraced these changes, recognizing that safety wasn't just a corporate mandate but an expression of genuine care. The results defied actuarial expectations. Within months, injury rates plummeted so dramatically that insurance statisticians visited headquarters in disbelief. "How did you do this?" they asked, puzzled by results that contradicted decades of industry data. "Kindness and math," was Rhee's simple reply. The company's improved safety record led to lower insurance premiums, and Rhee directed these savings toward merit-based raises for the store managers who had driven the improvement. This created a virtuous cycle where doing the right thing also made financial sense. Kindness at Ashley Stewart wasn't about random acts but intentional systems. Rhee established the CEO Citizenship Award, recognizing employees who embodied three criteria: "Do they act like an owner? Are they a good friend? Are they a good mentor?" A manager might have record-breaking sales, but if she didn't maintain morale, prioritize safety, or mentor colleagues, she wouldn't qualify. This award system reinforced that how results were achieved mattered as much as the results themselves. Communication patterns shifted too. When Rhee called store managers, they initially scrambled to report sales figures, assuming that's what he wanted. But his questions were different: "Did you get the inventory you need? Are you hiring the right people? And most important of all, are you good? Things okay?" These simple inquiries opened treasure chests of insight and built relationships based on mutual care rather than hierarchical control. What makes Rhee's approach revolutionary is how it integrates kindness into the very machinery of business operations. Rather than treating kindness as an add-on or corporate social responsibility initiative, he embedded it in every decision, measurement, and system. This integration created mathematical precision in an area often dismissed as soft or unmeasurable. The result was a company that not only survived against impossible odds but thrived by creating value that conventional metrics couldn't capture.

Chapter 4: Community Connections: The Economics of Authentic Relationships

When Chary, a store manager in Brick Church, New Jersey, emailed James Rhee asking if he would accompany her to a meeting at city hall, he immediately agreed. On the appointed day, they arrived together to discuss a potential public-private partnership. When the officials appeared, Rhee surprised Chary by introducing her and then whispering, "You're on." Though terrified of public speaking, Chary rose to the occasion brilliantly. Afterward, they celebrated over lunch with Shelley, another manager, and her children - a moment that transcended typical CEO-employee relationships. This scene captures the essence of Rhee's leadership philosophy: authentic connection that empowers others. Unlike executives who maintain careful distance from frontline workers, Rhee regularly called store managers just to check in. "Hey, it's James, how's everything going?" Initially confused by these calls, managers soon realized he genuinely cared about their wellbeing beyond sales figures. These conversations built trust that proved invaluable during challenging times. The company's transformation extended beyond its walls into the communities it served. Ashley Stewart stores functioned as neighborhood anchors where women gathered not just to shop but to find community. Managers knew customers' families, celebrated their achievements, and supported them through hardships. One manager regularly visited elderly customers in the hospital when they had no local family. Another kept track of customers' job interviews and family events, offering encouragement and practical support. During one particularly difficult period, Rhee organized a holiday party at the Brooklyn YWCA, which has provided safe haven for survivors of gender-based violence and immigrant women for over a century. Though the company had little to give materially, they donated sample merchandise and created a sales competition where the top forty stores earned the right to donate $250 to local charities of their choice. They also purchased bicycles for two local girls whose apartment building had recently burned down. These weren't calculated PR moves but expressions of the company's values. Rhee's approach to leadership challenged conventional wisdom about professional boundaries. He shared his own vulnerabilities, including his father's battle with Parkinson's disease and his struggles to balance work with family life. By revealing his humanity, he created space for others to do the same. This transparency fostered an environment where people brought their whole selves to work, eliminating the exhausting split between "Work-You" and "Home-You" that characterizes so many corporate cultures. Through this community-centered approach, Rhee demonstrated that business can be a powerful force for connection in an increasingly fragmented world. By valuing relationships as assets rather than costs, he created a model of leadership that honors our fundamental human need for belonging while delivering sustainable financial results. The connections formed through authentic leadership created resilience that sustained the company through industry disruptions that were decimating traditional retail.

Chapter 5: Measuring What Matters: Beyond Traditional Accounting

During his childhood, James was fascinated by baseball statistics. He collected cards and memorized batting averages, home runs, and runs batted in. As he grew older, he watched how baseball analytics evolved to include more sophisticated measurements like exit velocity and on-base percentage. Yet despite this statistical revolution, baseball began losing its magic for him. "There was too much data. Too many statisticians. The art, warmth, and intrigue of baseball, of stolen bases and sacrifice bunts, took a backseat," he reflects. This observation would later inform his approach to measurement at Ashley Stewart. When James signed the documents finalizing the sale of Ashley Stewart for a nine-figure sum, his feelings were surprisingly complex. While pleased with the financial outcome, he found himself contemplating the different ways we measure value in business versus life. In accounting terms, "goodwill" appears on a balance sheet only when someone pays more for a business than the fair value of its identifiable assets. It's a technical term used to make the numbers balance. But in life, goodwill represents something much more profound - the communal assets created through human connection and kindness. This distinction became painfully clear when James lost his father. At the wake, he was stunned to see the entire Ashley Stewart corporate office arrive to pay respects, despite his explicit instructions to keep the news private. Even more moving was the arrival of store managers like Chary, who had traveled directly from work. "You didn't tell anyone about your dad? Or about your daughter?" Chary asked, referring to a serious accident James's daughter had recently suffered. "You don't think for one second that we wouldn't find out and be here for you?" In that moment, James realized he was witnessing the true measurement of a life well-lived - how missed someone is when they're gone. At Ashley Stewart, James implemented alternative measurements that captured value traditional accounting missed. When tracking the company's e-commerce growth, he specifically measured how much profit came from higher-income neighborhoods outside their core communities. He viewed this as "capital surplus" that could fund investments back into the stores that served as community hubs. He tracked pregnancies among employees, seeing the rising numbers as evidence of growing confidence in the company's future. He measured the number of baby showers in the office, the reduction in sexual harassment incidents, and countless other indicators of a healthy culture. Perhaps most significantly, James created a measurement framework that balanced short-term results with long-term sustainability. He compared different clothing items to financial instruments - basic camis were like low-risk bonds that should deliver steady but modest returns, while fashion-forward items were like venture capital investments that might fail but could deliver outsized returns when successful. This portfolio approach reduced fear about individual mistakes and encouraged creativity. When a buyer purchased a blue prom dress that nobody wanted, James didn't punish her. "Is it really that awful?" he asked, acknowledging that occasional failures were built into the equation. Through these nuanced approaches to measurement, James demonstrated that what we choose to measure reflects our deepest values. Traditional accounting captures only a fraction of what makes a business - or a life - truly valuable. By expanding the definition of success beyond quarterly profits, Ashley Stewart created a more resilient and human-centered organization that could weather industry disruptions while maintaining its soul.

Chapter 6: The Red Helicopter Legacy: Transforming Business and Life

In Korean culture, the red dragonfly has special significance. Appearing in autumn, it symbolizes transformation, courage, and abundance. For James, autumn always marked significant transitions during his tenure at Ashley Stewart - from his arrival in Secaucus as the company faced liquidation to the annual Finding Ashley Stewart celebrations. It was also in autumn that his father passed away. Now, seven years into leading the company, another autumn brought profound change as James learned his mother had been diagnosed with late-stage pancreatic cancer. During her final days in hospice, James rarely left his mother's side. Their time together gave him new perspective on her life and his own. He had always viewed his Korean immigrant mother as someone who needed his protection, but he came to realize she was actually the strong one. She had survived war, the loss of her father, and countless indignities as an immigrant with limited English. What James had perceived as liabilities were actually her greatest assets - her resilience, determination, and unwavering kindness. She measured her life not by money or status, but by how she treated others, from handing tall glasses of icy water to lawn workers to passing out full-size candy bars to neighborhood children on Halloween. One memory particularly stood out: during a family relay race at a picnic, his mother had deliberately slowed down to let a young boy win. When James questioned her decision later, she replied firmly, "James—ya—did you really want your grown mom to race ahead and beat that boy? Is that what you want me to do?" In that moment, she taught him that true winning meant more than coming in first. It meant having the wisdom and grace to see beyond immediate victory to what truly matters. After his mother's passing, James made the decision to leave Ashley Stewart. The company had been successfully sold, ensuring its continuity, but he knew it was time to reinvest in the other legs of his three-legged stool: family and self. There was no emotional farewell party - James left quietly, knowing that true relationships transcend corporate structures. His parting advice to his team was simple: "You already know what is right. You already know what to do. You know what feels wrong, what you don't want to live with. So get to it." James gave himself six months to reconnect with his present and envision his future. He spent time in nature, fly-fishing in North Carolina and attempting to surf off the shores where he had once proposed to his wife. Though he was "awful at both," that wasn't the point. Amid that seeming imbalance, he found his balance again. When he emerged from this period of reflection, he accepted positions teaching at both MIT and Howard University - the latter being the same historically Black university where Korean students had first been recorded singing "Arirang," Korea's unofficial national anthem, in 1896. The red helicopter that once symbolized a moment of childhood connection had become a guiding principle for leadership that honors both kindness and math, both humanity and profit. Like a dragonfly that emerges transformed after spending most of its life underwater, James found that his greatest impact came not from following conventional paths but from embracing his whole self and creating space for others to do the same.

Summary

The transformation of Ashley Stewart from a twice-bankrupt retailer to a thriving business represents more than a financial turnaround - it offers a blueprint for integrating humanity into the very machinery of commerce. James Rhee's journey reveals that kindness isn't merely a pleasant addition to business but can be its fundamental operating system when combined with mathematical precision. By recognizing the value of relationships, trust, and community - assets that conventional accounting ignores - Rhee created sustainable growth while honoring the dignity of everyone in the company's ecosystem. The red helicopter story serves as a powerful metaphor throughout this journey. Just as a simple toy acknowledged a child's generosity, creating that "warm, good ache" of connection, businesses can design systems that recognize and amplify our better natures. When organizations align their operations with fundamental human values rather than artificial constructs, they unlock potential that transcends conventional metrics. This alignment isn't just morally satisfying but mathematically sound, generating returns that benefit all stakeholders. The lesson is clear: we don't need to choose between doing good and doing well. The most sustainable success comes from integrating both into a coherent whole that reflects the fullness of our humanity.

About Author

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James Rhee

James Rhee is a high school teacher, Harvard Law graduate, and private equity investor who became the unexpected Chairman and CEO of Ashley Stewart, where his transformative partnership with a primarily Black female employee and customer base shocked the business community and inspired the world. His TED Talk and Dare to Lead interview with Brené Brown have captured the imagination of millions. red helicopter—a parable for our times captures the full insights and essence of his unprecedented story.As the John H. Johnson Chair of Entrepreneurship and a Professor of Entrepreneurship at Howard University, James teaches the red helicopter operating system of life, money, and joy. He also teaches at MIT Sloan School of Management and Duke Law School, where his class, “The Way It All Works,” has been wildly popular for nearly a decade.James’s processes and ideas have been tested and proven in the private sector for over 25 years, and his influence continues to have an outsized impact with change-oriented leaders and organizations across many disciplines and industries. After helping manage billions of dollars of private equity in elite Boston-based firms, James started a family-office investment platform, FirePine Group, which has stewarded the capital of some of the world’s most sophisticated investors and continues to provide capital to entrepreneurs creating true systemic value. He serves on the Board of Directors of Xponance, a more than $16-billion asset management and investment firm focused on emerging manager strategies. And he is a former honoree of the EY Entrepreneur of the Year program, as well as a former board member of the National Retail Federation, whose foundation honored him with its Power Player Award, given to the CEOs who have the greatest impact on the future of retail. A charter member of the Advisory Council of JP Morgan Chase’s Advancing Black Pathways and the Governing Committee of the CEO Action for Racial Equity, James’s civic contributions have been recognized by multiple communities and groups: he was a Frederick Douglass honoree of the New York Urban League, the recipient of the Council of Korean Americans’ Trailblazer Award, and an honoree of One To World’s Fulbright Award. Global pioneer in social entrepreneurship Ashoka elected him as a member of its Entrepreneur-to-Entrepreneur Network. He also currently serves on the Board of Directors of Coalition for Asian American Children and Families and is a former director of Harvard University’s American Repertory Theater.Formerly an editor of Harvard Law Review, James has now written his first book, red helicopter―a parable for our times, and various music and multimedia projects related to it are in progress. He lives outside Boston with his wife and three children.

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