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

Facebook:

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

🎧 Listen on:

Spotify: [link coming soon]

Apple Podcasts: [link coming soon]

⚡ 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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