Todd Connor, Navy veteran and founder of Bunker Labs, breaks down what it takes to build mission-driven organizations that scale. Drawing on years of supporting veteran entrepreneurs, he shares candid insights on the realities of transitioning to civilian life, the pressures founders face, and the traits that separate those who succeed from those who stall. The conversation also explores his work with Veterans for All Voters and how the military-connected community can play a stabilizing role in a polarized environment.

COL Jeremy Gwinn offers a strategic lens on modern warfare, where economics, technology, and industrial capacity are as decisive as tactics on the battlefield. Drawing on experience from combat leadership to the Pentagon and now the Eisenhower School, he unpacks how nations resource and sustain war in an era of great power competition. The conversation explores the defense industrial base, emerging technologies, and the concept of reverse innovation, highlighting what leaders must understand to remain competitive in a rapidly evolving security environment.

General (Ret.) Paul E. Funk II delivers a direct and experience-driven perspective on leading in high-stakes, “must-win” environments. From commanding a 72-nation coalition against ISIS to shaping the Army’s future through TRADOC, he breaks down the leadership principles behind building resilient, high-performing organizations. The conversation explores talent management, training, and decision-making under pressure, along with his concept of “positively intrusive” leadership and what it takes to prepare the next generation to succeed in complex, rapidly changing environments.

Major (Ret.) Trisha Wyman brings a nuanced perspective on modern conflict, where influence, information, and technology shape outcomes as much as traditional force. Drawing on her experience in psychological operations and intelligence, she unpacks how disinformation, narrative control, and cognitive warfare are redefining the battlespace. The discussion also explores the challenges of operating in ambiguous environments, the intersection of data and decision-making, and how her work now bridges national security and the private sector.

General Larry Spencer, USAF (Ret.), reflects on a 40-year career that took him from the enlisted ranks to Vice Chief of Staff of the Air Force, offering hard-earned insights on leadership, risk, and resilience. He discusses how warfare and decision-making have evolved across domains, what it takes to drive innovation inside massive institutions, and how early experiences shape leaders at the highest levels. The conversation also examines his continued mission supporting service members and what meaningful leadership looks like beyond uniform.

LTG Bob Ashley, USA (Ret.), former Director of the Defense Intelligence Agency, offers a clear-eyed view into the realities of intelligence in modern warfare. Drawing on decades of experience across Iraq, Afghanistan, and senior strategic roles, he explains how intelligence truly supports decision-making, how it has evolved over years of conflict, and what outsiders often misunderstand about the discipline. The discussion also explores the impact of AI and open-source data, and what it takes to develop the next generation of intelligence leaders.

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.