The Intersection of Military Leadership and Entrepreneurship: Lessons from the Battlefield to the Boardroom and Everything in Between

Lessons from the Battlefield to the Boardroom: Leadership is often seen through the lens of two distinct worlds: the military and entrepreneurship. Yet, the principles that drive success in both arenas are remarkably similar. Military leadership is grounded in discipline, mission focus, and adaptability, while entrepreneurial leadership thrives on innovation, vision, and risk-taking. But where these two worlds intersect is in their shared demand for leading through uncertainty, inspiring teams, and making critical decisions under pressure. Trust is the one ingredient is the key to success in both environments.

As a leadership advisor and former Army officer, I’ve had the unique opportunity to lead in both the structured environment of the military and the unpredictable world of entrepreneurship. These experiences have given me insight into how military leadership principles can fuel entrepreneurial success, particularly in the high-stakes world of defense startups. In this article, I’ll explore the common threads between military leadership and entrepreneurship, share personal lessons learned, and offer practical advice for those navigating both paths.

The Criticality of Trust: The relationship between trust, psychological safety, and innovation is deeply intertwined and crucial for fostering a sustainably, high-performing, creative, and adaptable organizational culture. My flagship workshop and presentation is, Cultivating a Culture of Trust.

1. Trust: Trust is the foundation of any productive team. When team members trust one another, they believe in each other’s intentions and feel confident that their contributions will be respected. This mutual trust encourages open communication, collaboration, and risk-taking, all of which are essential for innovation.

2. Psychological Safety: Psychological safety refers to an environment where individuals feel safe to express their ideas, ask questions, and make mistakes without fear of negative consequences. Teams that prioritize psychological safety create spaces where team members are willing to be vulnerable, share unconventional ideas, and challenge the status quo—key ingredients for innovation.

3. Innovation: Innovation thrives in environments where people feel safe to experiment, share diverse perspectives, and push boundaries. Trust and psychological safety provide the emotional security needed to encourage these behaviors.

When individuals don’t fear judgment or retribution, they are more likely to propose creative solutions, engage in productive conflict, and experiment with novel ideas—resulting in more innovative outcomes.

The relationship is cyclical: trust supports the development of psychological safety, which in turn fosters innovation. As teams innovate and experience success, trust grows stronger, reinforcing a culture that continuously supports creativity and improvement. Without trust there really is no culture of innovation.

Comparing Leadership Challenges: Military vs. Entrepreneurship At first glance, military leadership and entrepreneurship may seem worlds apart. The military operates within a clearly defined hierarchy with well-established protocols, while startups are often chaotic, with leaders having to make decisions with little structure or certainty. However, both environments share the fundamental challenge of leading teams in the face of uncertainty.

In the military, the mission is clear, and while the stakes can be life or death, the objectives and resources are generally well-defined. In contrast, entrepreneurs often have to define their own mission, charting a path forward in a highly competitive, ever-changing landscape. Both roles demand resilience and adaptability, but where the military offers structure and support systems, entrepreneurship requires leaders to build those systems from scratch.

The rigor of leadership is tested differently in each environment. The emotional and mental strain of leading in combat is unparalleled, yet entrepreneurship brings its own relentless challenges. Financial risks, personal investments, and the constant need to pivot can stretch leadership capabilities to their limits. Ultimately, both require the ability to lead diverse teams toward a common goal in unpredictable conditions.

Adapting to Fluid Structures in Startups: One of the most significant differences between military leadership and entrepreneurship is the lack of hierarchy in startups. In the military, the chain of command is clear, and authority flows from rank. In a startup, however, leadership is less about title and more about influence and vision. You can’t rely on positional authority; instead, you need to establish credibility through trust and competence.

In startups, decision-making is more collaborative, and accountability can sometimes be unclear. To counter this, I’ve found it’s essential to foster open communication and clearly define roles and expectations. This helps maintain discipline and accountability without stifling the creativity and flexibility necessary for innovation.

Lessons from the Battlefield: Mission Focus and Adaptability The military teaches leaders to focus on the mission, even in the face of adversity. This same principle applies in entrepreneurship. Whether launching a new product or scaling a business, keeping your team aligned with a clear, achievable objective is crucial to success.

Adaptability is another key lesson from military leadership. Things rarely go according to plan in either the military or entrepreneurship. Leaders must be ready to adjust quickly without losing sight of the end goal. The OODA Loop—Observe, Orient, Decide, Act—is a military decision-making framework that has proven invaluable in fast-paced entrepreneurial environments. For example, when my startup faced a pivotal decision about a product pivot, I applied this framework, allowing us to move quickly and seize a market opportunity ahead of competitors.

Thriving in Uncertainty and Risk: Both military leaders and entrepreneurs operate in environments of uncertainty, where the cost of inaction can be high. In the military, leaders are trained to make decisions under pressure, often with incomplete information. This ability to compartmentalize fear and focus on the task at hand is a critical skill for entrepreneurs, who face the constant pressure of financial, market, and operational risks.

The military mindset of “acting, learning, and adjusting” is directly applicable to entrepreneurship. In both fields, you quickly learn that no decision is without risk, but inaction can be more detrimental than making a wrong decision. It’s better to make a decision, gather feedback, and pivot than to remain paralyzed by uncertainty.

Fostering Innovation through Discipline: Both the military and entrepreneurship value innovation, but their approaches differ. In the military, innovation is often driven by necessity. Leaders are taught to solve problems quickly and efficiently, often with limited resources. This mindset translates well to startups, where agility and resourcefulness are critical.

However, discipline plays a critical role in ensuring that innovation is aligned with strategic objectives. In both environments, leaders must strike a balance between fostering creativity and maintaining operational rigor. Setting clear parameters for what needs to be accomplished while giving teams the freedom to explore solutions has worked well in both my military and entrepreneurial experiences.

Leading with Values: Loyalty, Integrity, and Service Core values such as loyalty, integrity, and service are at the heart of military leadership, and they are equally important in entrepreneurship. In the military, leaders are entrusted with the lives of their team members, and integrity is non-negotiable. In the business world, while the stakes are different, these values build trust and foster strong teams.

In both settings, leaders are judged by their actions, not just their words. Consistently demonstrating these values establishes the foundation for long-term success. In business, just as in the military, people follow leaders they trust.

Balancing Profit and Purpose in Defense Start-ups: In the world of defense startups, leaders often face the dual responsibility of delivering returns to shareholders while contributing to national security. This creates a unique tension between profit and purpose. Navigating this balance requires a strong sense of mission. For me, it’s about ensuring that every business decision is grounded in both the impact on national security and the bottom line.

In defense startups, there’s no room for short-term thinking. Leaders must focus on sustainable success that serves both shareholders and the larger purpose of contributing to national security.

Leadership Failures and Lessons Learned: Leadership is a journey, and no leader is immune to failure. Early in my entrepreneurial career, I made the mistake of trying to control every aspect of the business, a habit carried over from my military background. This led to burnout and stifled the growth of my team. I quickly learned that successful leadership is about empowering others and delegating responsibility.

This lesson shaped my approach moving forward: trust your team, give them ownership, and focus on the bigger picture. Empowering others to lead not only builds a stronger team but also drives better outcomes for the business.

Advice for Veterans Transitioning to Entrepreneurship: For veterans moving into entrepreneurship, the transition can be challenging. The structured world of the military is vastly different from the chaos of startups. My advice is to embrace the unpredictability but carry forward the discipline and leadership principles you’ve learned. The ability to adapt, focus on mission success, and lead teams under pressure will serve you well in business.

I also recommend seeking out veteran entrepreneurial networks like Bunker Labs and defense-focused accelerators such as DIU, AFWERX and AAL. These communities provide not only resources but also a support system of people who understand your unique perspective. Additionally, government programs like the SBA’s Veteran-Owned Small Business programs can provide valuable assistance in the early stages of your entrepreneurial journey.

Conclusion: The intersection of military leadership and entrepreneurship is rich with lessons and opportunities. Both worlds demand resilience, adaptability, and a mission-focused mindset. As a leader, whether in the military or in business, your ability to inspire a shared vision, make decisions under pressure, and build a strong, high-trust, team will define your success.

For those transitioning from military service to entrepreneurship, the skills you’ve honed in the military give you a significant leadership advantage. Embrace the challenges of entrepreneurship, trust in your leadership training, and, most importantly, invest in your people. That’s the foundation of success in any environment, whether on the battlefield or in the boardroom.