Mike LeBlanc, former Marine officer and defense tech founder, brings a grounded perspective on building at the intersection of warfighting and innovation. From leading Marines in combat against ISIS to scaling venture-backed robotics companies, he unpacks what it takes to operate under uncertainty, lead high-performing teams, and translate battlefield experience into entrepreneurial success. The conversation explores the rise of autonomous systems in warfare, the realities behind defense startups, and the leadership mindset required to navigate risk, ethics, and rapid technological change.

Drawing on more than four decades of service, LTG Robert Caslen, USA (Ret.), unpacks the strategic and human dimensions of war, leadership, and national decision-making. From his role in shaping the Global War on Terror strategy to leading West Point and later a major public university, he offers a rare perspective on how wars are fought, how they end, and what leaders must carry long after. The conversation examines the Iraq withdrawal, the resurgence of ISIS, and the enduring importance of character, accountability, and disciplined leadership in moments of uncertainty and public scrutiny.

In this episode of Tipping Spears, William Bender, retired Air Force three-star general and former USAF CIO, offers a candid look at leading large-scale transformation at the intersection of defense, technology, and strategy. Drawing on his experience overseeing a $17 billion IT portfolio and shaping foundational cyber and data leadership roles across the Air Force, Bender breaks down what it takes to modernize bureaucratic institutions in real time. From standing up early innovation efforts that helped pave the way for today’s Defense Innovation Unit to navigating the complexities of industry-government collaboration, he provides a clear-eyed assessment of the challenges and opportunities facing today’s national security leaders in an era defined by AI, cyber threats, and great power competition.

Major Geoff Ball shares lessons from Marine Corps infantry leadership, spanning combat deployments, company command, and professional military education. From crisis response missions in CENTCOM to service at Abbey Gate during the Afghanistan withdrawal, he reflects on moments that reshaped his understanding of responsibility and sacrifice. He discusses the habits that distinguish exceptional junior officers from merely competent ones. Major Ball also explains why ownership of professional growth is essential in a rapidly evolving operational environment. The conversation highlights his work developing future leaders and fostering professional discourse across the force.

Major General Robert Edmonson II (USA, Ret.) discusses how infantry foundations shaped his leadership of large-scale IT and cybersecurity enterprises. As Commanding General of U.S. Army Communications-Electronics Command, he led a 9,000-person global workforce and a $3.1 billion portfolio supporting DoD operations worldwide. He explains what it means to modernize systems that never shut down and to drive change inside complex bureaucracies. MG Edmonson underscores that cybersecurity is fundamentally a people business, grounded in culture, trust, and accountability. The episode closes with a clear directive for senior leaders: develop enterprise judgment, accept 360-degree accountability, and invest in people as the decisive advantage.

LTG (Ret) Mike Ferriter shares lessons from 35 years of Army service, from combat in Mogadishu and Iraq to commanding a global enterprise spanning 75 installations and 17 time zones. He explains how early platoon leadership shaped his approach to leading large, complex organizations through crisis and transformation. Ferriter discusses decision-making under pressure, capability prioritization for multi-domain operations, and why “winners leave clues.” He reflects on building and leading the National Veterans Memorial and Museum, including navigating the COVID-19 pandemic while expanding national impact. The episode concludes with direct advice for veterans in transition and a call to renew a culture of service and responsibility.

General (Ret) Charles A. Flynn reflects on his evolution from a self-described reluctant cadet to Commanding General of U.S. Army Pacific, leading operations across the Army’s largest theater. He explains why intellectual curiosity is indispensable for senior leaders navigating ambiguity and strategic competition. General Flynn offers a clear-eyed assessment of the Indo-Pacific, the pacing challenge posed by the Chinese Communist Party, and why land power remains central to credible deterrence. He unpacks the concepts of lethality, strategic unpredictability, and alliance integration in preventing conflict. The conversation closes with candid insights on character, judgment under pressure, and building resilient organizations that endure beyond any single commander.