Monica Lewinsky
Anti-Bullying Activist & Cultural Commentator | Emmy-Nominated Producer | TED Speaker with 20M+ Views | Advocate for Digital Civility & Compassion
"The Wingman" | Lt. Col. (ret.), U.S. Air Force | Decorated F-16 Combat Pilot, 65 Missions | NSA Speaker Hall of Fame | NYT & WSJ Bestselling Author
Lt. Col. (ret.) Waldo Waldman flew 65 real-world combat missions in an F-16 after overcoming a lifelong fear of heights and claustrophobia — and built a career helping organizations apply those same lessons of courage, trust, and teamwork to business. A New York Times and Wall Street Journal bestselling author and one of fewer than 200 inductees into the NSA Speaker Hall of Fame, "The Wingman" gives audiences the tools to lead with courage and never fly solo.
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Known as “The Wingman,” Lt. Col. (ret.) Rob “Waldo” Waldman is one of the most decorated figures in the professional speaking world — a combat veteran, bestselling author, and Hall of Fame keynote speaker who has spent decades translating the high-stakes lessons of fighter pilot culture into frameworks that transform how organizations lead, collaborate, and perform. As a leadership speaker, Waldo Waldman draws on 65 real-world combat missions and 2,650 flight hours in an F-16 Fighting Falcon to deliver a message that lands with equal force in a sales kickoff, a safety conference, or a senior leadership summit: in business and in life, you should never fly solo.
Waldman grew up on Long Island, the son of a Navy veteran and JFK Airport mechanic who instilled in him a love of flight. He went on to graduate from the United States Air Force Academy in 1990 and earn an MBA with a focus on Organizational Behavior — all while battling severe claustrophobia and a fear of heights. That private struggle, and his decision to face it head-on rather than walk away from his dream of flying, became the defining arc of his story and the foundation of everything he teaches about courage, commitment, and the power of trusting your wingmen. He flew combat missions over Iraq enforcing the no-fly zone and in Yugoslavia during Operation Allied Force, earning five Air Medals, two Aerial Achievement Medals, four Air Force Commendation Medals, and two Meritorious Service Medals.
After retiring from the Air Force, Waldman moved into the private sector — leading national sales efforts for cutting-edge technology and consulting firms and building real-world commercial credibility before founding Wingman Enterprises, his Atlanta-based leadership consulting firm. His book Never Fly Solo: Lead with Courage, Build Trusting Partnerships, and Reach New Heights in Business (McGraw-Hill) became a simultaneous New York Times and Wall Street Journal bestseller and has been endorsed by world-class business minds including Marshall Goldsmith and Jeffrey Gitomer. Endorsed by leaders from Howard Putnam, former CEO of Southwest Airlines, to Keith Ferrazzi, the book is a blueprint for building the kind of mutual accountability that drives elite performance.
Waldman has been inducted into the National Speakers Association Speaker Hall of Fame — the Council of Peers Award for Excellence (CPAE) — one of fewer than 200 speakers worldwide to receive this lifetime honor since 1977, alongside names including Colin Powell, Zig Ziglar, and Ronald Reagan. He also holds the Certified Speaking Professional (CSP) designation, the highest earned credential in the professional speaking industry, held by just 7% of all professional speakers globally. His client roster spans some of the world’s most recognizable organizations: Verizon, American Express, Johnson & Johnson, Hewlett-Packard, Siemens, ExxonMobil, Marriott, Aflac, MassMutual, the Denver Broncos, and dozens more across healthcare, financial services, manufacturing, and real estate.
As a speaker, Waldo Waldman is high-energy, deeply personal, and relentlessly practical. He uses dramatic F-16 combat footage, real mission debriefs, and audience interaction to bring the wingman philosophy to life — showing leaders at every level how the principles of disciplined preparation, courageous communication, servant leadership, and mutual trust produce results in the most demanding environments on earth. Attendees leave not just inspired but equipped: with a language, a mindset, and a specific set of tools they can deploy the next day with their teams.
Waldo's signature keynote — the one behind the bestselling book — is a high-energy, multimedia experience that uses F-16 combat footage, mission debrief methodology, and vivid personal storytelling to show any audience what peak performance actually looks like under pressure. Participants leave with the wingman framework: a practical model built on disciplined preparation, courageous communication, mutual accountability, and servant leadership that can be applied immediately across any team or organization.
In this program designed for senior leaders and managers, Waldman draws the critical distinction between managing people and leading them — and shows what it takes to build a culture where every team member feels personally accountable for the mission's success. Drawing on his experience as a combat flight lead responsible for the lives of his wingmen, he delivers proven tools for building cultures of trust, excellence, and shared commitment that outperform in even the most turbulent competitive environments.
Change and uncertainty are the permanent conditions of modern business — and the organizations that thrive are those that have built the psychological and structural muscle to face them without flinching. Waldman draws on his personal story of overcoming severe claustrophobia and a fear of heights to earn his wings, and on the high-pressure protocols of combat aviation, to give leaders a concrete framework for building resilience, embracing discomfort, and making courageous decisions when the stakes are highest.
Adapted for safety-critical industries — healthcare, construction, energy, manufacturing — this program applies the standards of combat aviation to the goal of zero-incident operations. Waldman covers the cultural elements that prevent complacency: clear accountability structures, two-way communication, values-based leadership, and the relentless commitment to standards that keeps wingmen alive in the cockpit and workers safe on the floor. Clients include ExxonMobil, Duke University Hospital, Shell, Bosch, and the National Fire Protection Agency.
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