In this episode of Diehard Entrepreneur Stories, we sit down with Terry Wilson, founder of Tactical Edge Coaching & Consulting and a 24-year military veteran, most of it spent in U.S. Special Forces. Known as “Trailer” in the military, Terry shares a raw and powerful conversation on leadership, resilience, and purpose.
We take a step away from business talk to focus on leadership—how to lead through chaos, build high-performing teams, and develop others intentionally. Terry opens up about his tough childhood in St. Louis and how it shaped his drive. His military career post-9/11 taught him the value of human connection and leading by, with, and through people.
He draws lessons from the battlefield that apply to entrepreneurship—like letting your team create and execute the plan, holding people to a clear standard, and measuring success by how well you serve others. After losing his son in 2020, Terry’s view of success changed. He speaks openly about grief, rebuilding himself physically and spiritually, and being present with family.
Terry shares his SPEAR Framework, which emphasizes mental toughness, faith, physical fitness, and living with purpose. He believes your purpose should be bigger than you—something no one can take away.
This is more than a leadership episode—it’s a story of transformation, healing, and living with intention. If you're navigating loss, chaos, or the pressures of leadership, this conversation will hit home.
🛡️ Stay hungry. Stay humble. Stay frosty.
Connect with Terry Wilson:
Instagram: https://www.instagram.com/terry.m.wilson.jr
TIMESTAMPS
00:00 – Meet Terry “Trailer” Wilson: Special Forces Vet & Leadership Coach
02:03 – A Rough Start: Terry’s Childhood in St. Louis & St. Charles
09:00 – Life in Special Forces: Discipline, Chaos & Purpose
12:55 – Military Teams vs Entrepreneurship: What Carries Over
17:03 – True Leadership: Building Others Up, Not Doing It All
21:26 – How Terry Helps People Reach Their Full Potential
26:59 – Giving Impactful Feedback Without Breaking Trust
32:52 – Terry’s Go-To Strategies to Motivate and Inspire
38:04 – Rock Bottom: Losing His Son & Rebuilding from Pain
45:18 – Changing How People Think & Find Their “Why”
47:29 – The SPEAR Framework: A Blueprint for Complete Leadership
51:04 – What Purpose Really Means (And How to Find Yours)
53:30 – Terry’s Journey to Rediscover His Own Purpose
57:47 – Why Men Are Leaders by Default—and What That Really Means
1:04:26 – Reaffirming Your Purpose Through Faith & Action
1:06:35 – Terry’s New Definition of Success (Post-Tragedy)
1:09:27 – Purpose Over Goals: What Really Drives Long-Term Fulfillment
🎧 Watch on Youtube:
https://youtu.be/rD-_kwRHlUw
⚡ Let's stay in touch:
Instagram: https://www.instagram.com/devinramos/
Facebook: https://web.facebook.com/devinjramos035/
LinkedIn: https://www.linkedin.com/in/devin-ramos-602a811ab/
🎬 Produced by:
https://daretopodcast.com/
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