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/

#DiehardEntrepreneurStories #LindsayArko #RealEstateLeadership #TeamBuilding #CoreValues #Delegation #SalesStrategy #LeadershipGrowth #EntrepreneurMindset #BlackjackRealEstate #BusinessSuccess #WomenInBusiness #PurposeDrivenEntrepreneur #DevinRamosPodcast #ForwardFactor #DevinRamos

Hosted on Acast. See acast.com/privacy for more information.

In this episode of Diehard Entrepreneur Stories, Lindsay Arko shares her inspiring journey from corporate America to becoming the COO of Blackjack Real Estate, highlighting the pursuit of both income and time freedom. She discusses the mindset shifts required to transition successfully, emphasizing how stepping away from doing everything yourself to leading a strong, values-driven team is vital. Lindsay reveals how establishing core values and clear standards fuels team cohesion, accountability, and creates a culture where leaders develop other leaders.

Lindsay dives deeper into the challenges of letting go of control and trusting her team, noting that effective communication and consistent training are essential for growth. She shares how evolving sales strategies—inspired by problem-solving rather than mere rapport-building—have contributed to Blackjack Real Estate’s success. Lindsay stresses that investing time and commitment in team development not only enhances performance but also drives long-term sustainability in business.

As the conversation wraps up, Lindsay reflects on the importance of adaptability in navigating a changing market, and the value of slowing down to focus on what truly matters. She offers thoughtful insights on leadership, resilience, and creating a thriving company culture, making this episode a must-listen for entrepreneurs ready to empower their teams and embrace purposeful growth.

I’m on a MISSION to help entrepreneurs build strong, successful businesses.

Get on board at: 🤝https://www.devinramos.com

Connect with Lindsay Arko:

Instagram | Facebook

TIMESTAMPS

00:00 Introduction

01:55 From Corporate to Real Estate

05:23 When to take the Leap

08:45 Defining Success vs Failure

10:16 Lindsay’s Sales Experience

13:37 Establishing Core Value Alignment and Standards

19:00 Building a Team and Hiring Right

24:36 Handling Breaking Points

28:41 Biggest Mistakes Entrepreneurs Make

33:22 Letting Go: The Challenge of Delegation

37:00 Empowering Your Team to Lead

42:11 Evolving Sales Strategies for Success

47:48 Commitment to Leadership, Growth and Team Development

49:40 The Ability to Cater Different Markets

52:24 Set-up Your Non-negotiables

56:58 Slowing Down to not Miss Out on what Matter

1:01:16 What’s in the Horizon for Lindsay Arko

Watch on YouTube:

https://youtu.be/Jy1Zs99XH_w

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬 Produced by:

https://daretopodcast.com/

#DiehardEntrepreneurStories #LindsayArko #RealEstateLeadership #TeamBuilding #CoreValues #Delegation #SalesStrategy #LeadershipGrowth #EntrepreneurMindset #BlackjackRealEstate #BusinessSuccess #WomenInBusiness #PurposeDrivenEntrepreneur #DevinRamosPodcast #ForwardFactor #DevinRamos

Hosted on Acast. See acast.com/privacy for more information.

Want to finally take control of your time and get more done — without burning out?

In this episode of Diehard Entrepreneur Stories, I’m sharing five productivity strategies that have shaped how I run my life and business — straight from my own journey, including lessons from my military background.

This isn’t about working longer hours or forcing discipline. It’s about using a proven framework to make better decisions, stay focused, and actually feel good about the work you’re doing.

I will walk you through the exact steps I use to boost productivity — from taking inventory of your tasks to planning ahead, removing distractions, and understanding when to eliminate or delegate. Each tip is backed by real-life application and designed to help you create more output with less wasted effort.

If you’ve been feeling overwhelmed or stretched thin, this episode gives you the mindset and tools to shift from reactive to intentional.

I’m on a MISSION to help entrepreneurs build strong, successful businesses.

Get on board at: 🤝

https://www.devinramos.com

TIMESTAMPS

00:00 Defining Productivity and Its Importance

01:34 What is Productivity?

03:24 The Journey to Understanding Productivity

06:21 Tip #1 Take an Inventory

09:13 Tip #2Plan the Night Before

12:16 Tip #3 Learn to Prioritize

17:50 Tip #4 Removing Distractions

26:27 Tip #5 Eliminate & Delegate

30:58 Final Message

🎬Watch this on Youtube:

[We’ll Insert the Link once Published]

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬Produced by:

https://daretopodcast.com/

#DiehardEntrepreneur #ProductivityFramework #MilitaryDiscipline #EntrepreneurFocus #WorkWithIntention #EliminateToGrow #HighPerformanceHabits #BusinessWithoutBurnout #DelegateSmart #DailySuccess #PrioritizeLikeAPro #FocusAndExecute #EntrepreneurMindset #TimeManagementTips #DisciplineEqualsFreedom #SuccessHabits #StrategicPlanning #DoMoreWithLess #FoundersLife #LeadershipDevelopment #PeakPerformance #NoExcuses #BuildBetterHabits #SystemsOverHustle #MentalClarity #OwnYourTime #IntentionalLiving #GrowthDriven #ForwardFactor #DevinRamos

Hosted on Acast. See acast.com/privacy for more information.