James Rhee is a globally recognized entrepreneur, investor, educator, author, and former CEO whose career has been shaped by a belief that kindness, purpose, and strong business fundamentals can work together to create meaningful and lasting change.
A former high school teacher, James graduated with honors from Harvard College and Harvard Law School, where he served as an editor of the Harvard Law Review. He went on to build a successful career in private equity and investing, helping manage billions of dollars in capital before founding his own investment platform, FirePine Group.
James gained international attention during his seven-year tenure as owner, Chairman, and CEO of Ashley Stewart, a fashion retailer with deep roots in the Black American community. When James became involved, the twice-bankrupt company was facing enormous financial challenges. Working alongside its predominantly Black female workforce, he helped lead an extraordinary turnaround by combining rigorous financial thinking with trust, relationships, and human connection—an approach he calls “Kindness and Math.”
Those experiences helped inspire his bestselling book, red helicopter—a parable for our times: lead change with kindness (plus a little math). Published in 2024, the book explores leadership, business, humanity, and how people can balance life, money, purpose, and joy. Its ideas have since expanded into Red Helicopter, a broader media, investment, and education platform.
James has also devoted a significant part of his career to education. He has served as the Johnson Chair of Entrepreneurship and Professor of Entrepreneurship at Howard University and has taught at MIT Sloan School of Management and Duke Law School. At Yale University, he has served as an entrepreneur and artist in residence, bringing together his interests in business, education, storytelling, and music. His book even inspired Red Helicopter: An American Rock Opera, which debuted at Yale in 2026.
Beyond education, James continues to advise business leaders and organizations and serves on the board of Xponance, a major asset-management firm. His leadership and impact have been recognized by organizations spanning business, education, entrepreneurship, technology, retail, and civic leadership.
Despite his many accomplishments, the philosophy behind James's work can be traced to a simple childhood experience. As a five-year-old, he shared his lunch with a classmate who sometimes came to school without one. The child's father later gave James a toy red helicopter as a gesture of gratitude. That experience became a lifelong symbol of the extraordinary impact that seemingly small acts of kindness can have.
When James joins us, students will have the opportunity to learn about his journey from teacher to investor and CEO, entrepreneurship, leadership, overcoming challenges, defining success, and why kindness and human connection can be every bit as important as numbers and achievement.
