EP 334: Rey Ramsey's one way ticket is to the time of Socrates.

One teacher saw what others had missed—and changed the course of Rey Ramsey’s life.

After being mocked in the classroom and labeled “Oblivious,” Rey stopped raising his hand for three years. Then his sixth-grade teacher, Mrs. Elizabeth Ann Peiffer, told him something no one else had: He was one of the smartest students in the school. That moment restored his confidence and helped ignite an extraordinary journey to becoming a CEO, social-impact leader, and author.

In this powerful conversation with host Steven Shalowitz, Rey reveals how limiting expectations, false narratives, social pressure, and internal doubt can shape our choices without us realizing it. He shares practical insights from his new book, “The Tyranny of False Choices: A Guide to Authentic Decision-Making,” on critical thinking, leadership, resilience, and reclaiming agency in a deeply divided world.

The conversation also explores why algorithms reinforce our existing beliefs, how to disagree without dehumanizing one another, what humility, courage, and perseverance teach us about leadership, why Rey would take his one-way ticket to meet Socrates—and how one person’s belief in us can transform an entire life.

Now, let’s raise the question: “What teacher, mentor, or unexpected person changed the direction of your life?” Do share your story.

ABOUT THE GUEST

Rey Ramsey is a social justice entrepreneur and boundary-crossing leader with more than three decades of experience spanning the nonprofit, public, and private sectors. He is President and CEO of the Nathan Cummings Foundation and Founder and CEO of Centri Capital.

His distinguished career includes serving as Oregon’s Director of Housing and Community Services, Chairman of Habitat for Humanity International, and founding CEO and Chairman of One Economy Corporation, a nonprofit provider of internet services to low-income homes.

Additionally, Rey served as President and CEO of TechNet, a bipartisan network of tech executives representing two million employees and $800 billion in revenues. He has served as Chairman of the NAACP Futures Commission, and now serves as a director on numerous boards, including Morgan Stanley Institute for Sustainability, MMGL Real Estate, and the Local Initiatives Support Corporation (LISC).

Rey is also the author of Tyranny of False Choices: A Guide to Authentic Decision-Making, published by Forbes Books on March 17, 2026.

ABOUT THE NATHAN CUMMINGS FOUNDATION

Nathan Cummings Foundation (NCF) is a multigenerational family foundation honoring the Jewish tradition of social justice. NCF is working to shift power structures to co-create a more just, vibrant, sustainable, and democratic society. We support movements, change makers, and social entrepreneurs who are crafting solutions that advance racial, economic, and environmental justice.