Episode 28 Brandon Jenkins
Leadership, Resilience, and Financial Readiness
Tales of Leadership | Episode 28 | Brandon Jenkins
In this episode of Tales of Leadership, Joshua McMillion sits down with Brandon Jenkins, a retired Naval officer, MH-60 Romeo helicopter pilot, real estate investor, and founder of One Life Insurance LLC. Brandon’s story blends military leadership, financial growth, and personal development into one clear message: leadership is about making the people around you better. From the very beginning, Brandon frames leadership through the lens of teamwork. He explains that the best leaders are not simply the ones who hold authority, but the ones who improve the team by helping others grow, solve problems, and align around a shared mission. The best leaders make the people around them better.
Brandon talks about how that definition has evolved throughout his Navy career. Early on, leadership looked more like authority and responsibility. Over time, it became more about influence, trust, and helping others step into their own potential. He emphasizes that a leader cannot be everywhere at once, so the real goal is to create a team where people at every level understand the mission, carry the philosophy forward, and are trusted to act. This is where his thoughts connect to the idea of mission command. Delegating authority is not about avoiding responsibility. It is about building a stronger and more resilient team by giving the right people ownership within the right boundaries. Delegation is not about giving work away—it is about developing people and building resilient teams.
A major theme throughout the conversation is humility. Brandon makes it clear that leadership growth starts by understanding that you will never know everything. He reflects on his early days in the Navy and how important it was to show up with a learning mindset. Rather than pretending to have all the answers, he learned to ask what he could learn from every role, every mentor, and every challenge. That humility allowed him to absorb lessons, improve his craft, and eventually lead others more effectively. A humble leader learns faster, grows faster, and leads better.
Joshua and Brandon also spend significant time discussing the importance of self-leadership. Before someone can effectively lead a team, they must know who they are, what they value, and how they want to show up. Brandon shares how powerful it was for him to get clear on his core values, his why, and the type of leader he wanted to be. He credits coaching with helping him think more deeply, reflect more intentionally, and align his decisions with who he actually is rather than just reacting to circumstances. You cannot lead others well until you know who you are and what you stand for.
That clarity became especially important when Brandon moved into command. He talks about taking over a squadron and realizing that effective leadership in those moments starts long before the first briefing or command speech. It starts with the hard internal work of getting clear on your philosophy, your values, and your approach. From there, he brought in his inner team, gathered feedback, and refined the vision before trying to lead the larger organization. Once in command, he did not want his philosophy to be just a statement on the wall. He made it practical by getting out of the office, walking through the workspaces, talking to people, listening to pain points, and staying connected to the pulse of the unit. If your leadership philosophy only exists on paper, it is not leadership.
Another key lesson from the episode is that leadership operates in the gray. Brandon explains that there is rarely a perfect checklist for leadership problems because people, teams, and missions are too complex for that. Technical processes matter, but human systems require judgment, awareness, and flexibility. That is why feedback is so important. The higher someone rises in leadership, the easier it becomes for honest feedback to disappear. Brandon emphasizes the need to create space for truth, to stay connected to the team, and to intentionally seek out what is really happening in the organization before small issues become major failures. Leaders must create feedback loops because leadership problems rarely come with a checklist answer.
The conversation also moves into financial leadership and personal responsibility. Brandon shares how his interest in real estate and financial strategy began with a personal realization that the way he was managing money was not aligned with the life he wanted to build. That experience sparked a new path of learning, investing, and eventually helping others. For him, financial readiness is not separate from leadership. It is another area where intentionality, discipline, and long-term thinking matter. That is also what drew him into the War Room mastermind, where accountability, consistency, and shared growth continue to sharpen him. Financial growth, like leadership growth, starts with ownership and intentional learning.
Brandon returns often to the importance of strong teams. Whether in the military, in business, or in personal development, he believes that growth happens best when people surround themselves with others who will challenge them, support them, and hold them accountable. That is why he values mastermind communities so much. It is also why he keeps coming back to resilience. Plans matter, but life always gets a vote. The best teams are not the ones with the prettiest plan on paper. They are the ones that can adapt, recover, and keep moving when circumstances change. Resilience is what keeps a team moving when the plan gets punched in the face.
By the end of the episode, Brandon’s message is clear. Leadership is not about titles, control, or personal success. It is about humility, learning, trust, feedback, resilience, and making the people around you better. When leaders know themselves, stay teachable, and stay connected to their teams, they create organizations that are capable of far more than any one person could ever accomplish alone. Great leadership is the constant work of developing yourself so you can better develop others.
Final Thoughts
This episode is a reminder that leadership starts with self-awareness and grows through humility. Brandon Jenkins shows that the strongest leaders are not the ones pretending to know it all. They are the ones who stay grounded, stay curious, and stay committed to making their teams better. His reflections on mission command, feedback, resilience, and personal development all point to the same truth: leadership is about building trust and multiplying strength in others. If you want to lead well, start by doing the hard work on yourself and then use that growth to lift your team.
After Action Review
Am I delegating in a way that develops my team, or am I just trying to get work off my plate?
What feedback loops do I have in place to make sure I know what is really happening in my organization?
Have I done the internal work to clearly define my values, my why, and the kind of leader I want to be?
Tales of Leadership Mission: To develop Purposeful Accountable Leaders (PAL)
by arming you with the tools required to lead with purpose, integrity, and accountability.
More Exclusive Content
Learn how purposeful, accountable leaders (PALs) overcome failure by taking ownership, using the STOP framework, controlling emotions, addressing problems quickly, and building an inner circle that demands growth. This article in the LEADERS FAIL series explains why accountability is the bridge between failure and leadership growth.