In this episode, we engage in a profound discourse with Chris Scherrian, an entrepreneur whose journey epitomizes resilience, reinvention, and unwavering determination. Chris shares invaluable insights garnered from his extensive experience in navigating the complexities of business ownership, including the emotionally fraught process of downsizing and the inherent challenges of leadership during turbulent times. He elucidates the often unseen sacrifices made by entrepreneurs in their efforts to sustain their teams, emphasizing the critical balance between financial viability and employee morale. Our conversation delves into the importance of fostering a positive organizational culture, where employees feel valued and empowered, thus enhancing overall performance and commitment. As we explore these themes, we aim to provide listeners with actionable lessons in leadership that resonate across various industries and professional landscapes. Resilience and tenacity characterize the extraordinary journey of Chris Scherrian, who has transformed his life and the lives of others through his entrepreneurial ventures. In this enlightening discussion, Chris shares his experiences of battling cancer, completing two Ironman triathlons, and navigating the tumultuous waters of starting and rebuilding businesses across various industries. As the founder of Bootstraps and Battle Scars and the creator of Founders Exchange, he offers invaluable insights into the gritty realities of entrepreneurship, emphasizing the importance of unfiltered leadership lessons. This episode delves into the emotional and psychological toll of business challenges, including the arduous decisions of letting go of employees during tough times. Chris articulates the complexities of maintaining morale within a team while facing financial uncertainties, illustrating how these experiences have shaped his leadership philosophy and approach to guiding aspiring entrepreneurs towards success. The dialogue further explores the dichotomy of leadership in corporate environments compared to military contexts. The insights provided by the speakers reveal the multifaceted nature of leadership, emphasizing that effective leaders must blend empathy with a clear focus on organizational goals. The conversation touches on the necessity of maintaining a positive atmosphere while confronting harsh realities, and the pivotal role of communication in fostering a cohesive team culture. As the discussion unfolds, listeners are invited to reflect on their own leadership styles and consider how they can cultivate an environment that encourages growth, accountability, and resilience among their teams. Ultimately, this episode serves as a profound reminder that leadership is not merely about authority or position; it is about inspiring others through actions and decisions that reflect integrity and purpose. Chris's journey embodies the essence of perseverance and determination, offering a beacon of hope and guidance for those navigating their own entrepreneurial paths. Through candid anecdotes and practical advice, the episode imparts essential lessons on leadership, resilience, and the human experience in the pursuit of success.

Takeaways:

1. The episode features Chris Scherrian, an entrepreneur renowned for his resilience and grit in navigating business challenges.
2. Chris's journey includes surviving cancer and completing two Ironman competitions, showcasing his tenacity in both personal and professional realms.
3. The conversation emphasizes the emotional toll on leaders during difficult business decisions, particularly when laying off employees.
4. Leadership in challenging times...

Brad Lehman, a retired U.S. Marine Corps lieutenant colonel and F-35 test pilot, joins The Real Leadership Brief to discuss how leaders make decisions under pressure. Drawing from his experience in high-stakes military environments and his transition into entrepreneurship, Brad shares what preparation, execution, and accountability really look like when mistakes have consequences.

The conversation explores how military leadership principles translate into business, why trust and responsibility matter more than authority, and how leaders adapt when moving from life-or-death decisions to the civilian world. We also discuss Brad’s work as the founder of SwingSesh, and what it means to lead by example while building systems that support performance, teamwork, and resilience.

1. Leadership under pressure depends on preparation and clarity, not authority.
2. Military and civilian leadership require different approaches, but the same accountability.
3. High-stakes decision-making leaves no room for ego or indecision.
4. Transitioning from military to civilian leadership requires adaptation, not reinvention.
5. Strong leaders know when to lead and when to rely on others’ expertise.
6. Building effective systems matters more than individual heroics.

1. https://swingsesh.com
2. https://teamswingsesh.com

Company mentioned: SwingSesh

This episode of Spirits and Stories with Donald Dunn explores the often-unspoken realities of military service and the transition to civilian life through the story of Paul, a veteran who joined the military for practical reasons rather than idealism. He reflects on the motivations that led him to enlist, the financial decisions many young service members face, and the lessons learned through experience, mistakes, and growth.

Through candid and often humorous stories, the conversation examines how military life shapes identity, accountability, and resilience—and how those traits carry over into life after the uniform comes off. The episode also touches on the challenges of adapting to civilian roles, the pressure to appear successful despite personal struggles, and the different paths veterans take as they rebuild purpose and direction, including entrepreneurship.

At its core, this episode is about identity, adaptation, and the human side of life after service.

Takeaways

Many service members enlist for practical or financial reasons rather than patriotism alone.

Young soldiers often struggle with financial responsibility early in their careers.

Military service builds accountability and leadership, but those skills must be adapted for civilian life.

Transitioning out of the military can be challenging and disorienting.

Veterans often find new purpose by applying their experience to business, creativity, or entrepreneurship.

Links

nashvilleadventures.com

Companies mentioned

Singular

Amazon

Nashville Adventures