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.

What can a former CIA officer teach us about leadership, legacy, and getting things done — in life and in business?

In this episode of Diehard Entrepreneur Stories, I sit down with my friend and mentor Ric Prado, author of Black Ops: The Life of a CIA Shadow Warrior. Ric spent 24 years with the CIA, served as Vice President at Blackwater, and now runs his own company while mentoring the next generation of leaders.

From escaping Cuba as an orphan to leading high-risk covert operations around the world, Ric’s story is one of resilience, discipline, and service. We dive into what it means to lead with integrity, how to build trust in high-stakes environments, and why understanding people — not just systems — is the real secret to success.

Whether you’re growing a team, scaling a company, or just trying to become a better leader, Ric’s insights on intentionality, recruitment, and legacy are powerful and deeply applicable to everyday life and business.

💡 If you care about leadership that actually lasts — and impact that goes far beyond titles — this conversation will hit home.

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

Get on board at: 🤝

https://www.devinramos.com

Learn more about Ric Prado’s journey and grab his book:

🌐 https://www.ricprado.com/

TIMESTAMPS

00:00 Introduction

02:03 Ric Prado Early Life and the Impact of Trauma

05:36 Military Training and the Path to CIA

10:13 Experiences in Nicaragua and Black Ops

12:38 Intentionality in Operations

18:30 The Importance of Relationships

30:26 Recruitment Strategies and Business Parallels

31:53 The Whiffem Principle

34:11 Leadership and Mentorship

38:36 Legacy and Impact of Leadership

41:50 Leadership Lessons and Team Dynamics

50:46 Missed Opportunities in Counterterrorism

55:03 The Importance of Diplomacy in Operations

58:54 Building Effective Teams

1:04:51 Navigating Transition and Identity

1:15:19 Ric Prado Current Ventures and What’s in his Horizon

1:20:38 Ric Prado’s Book

1:25:27 Ric Prado’s Definition to Wealth and Legacy

1:29:00 Ric Prado’s Message to You

1:30:12 Black Ops: Life of a CIA Shadow Warrior & Connect with Rico Prado

🎬Watch this on Youtube:

https://youtu.be/DCdoQ1enOXk

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬Produced by:

https://daretopodcast.com/

#DiehardEntrepreneur #RicPrado #CIALeadership #ShadowWarrior #LegacyDriven #IntentionalLiving #HighPerformanceLeadership #EntrepreneurMindset #BusinessAndWarfare #WhiffemPrinciple #ResilientLeadership #MentorshipMatters #BlackOps #FromOrphanToOperative #MissionMindset #TeamBuilding #LeadershipLegacy #DisciplineEqualsFreedom #TacticalWisdom #RealLeadership #BuildTrustLeadWell #Forward Factor #DevinRamos

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

In this inspiring episode of Diehard Entrepreneur Stories, Anthony Autry shares the transformative path that shaped him into a purpose-driven entrepreneur, mentor, and leader. Through discipline, community, and an unwavering commitment to growth, Anthony has created a life centered around service and impact.

He reveals how establishing structure in his daily life became the foundation for both personal development and business success. From leading in recovery spaces to building thriving communities, Anthony speaks on the power of mindset, the value of authenticity, and how tools used for personal growth can directly apply to leadership and entrepreneurship.

If you're passionate about growth, leadership, and living intentionally—this episode will give you a fresh perspective and the motivation to stay aligned with your purpose.

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

Get on board at: 🤝

https://www.devinramos.com

Connect with Anthony Autry:

Instagram:

https://www.instagram.com/unchained_fit/?hl=en

TIMESTAMP

00:00 Introduction

02:28 Anthony Autry’s Life Transformation

15:32 People, Places and Things

18:00 Finding Purpose and Building a Future

19:37 Unchained Fit’s Story

21:26 The Journey of Sobriety and Accountability

25:01 Tools for Life: Recovery and Business

29:53 Finding Purpose After Prison

36:09 Not Giving Up

31:16 Formulating a Transformational Program

34:06 Leadership and Personal Development

41:58 Building a Thriving Community

44:04 Greatest Lessons Anthony Learned

52:37 Tracking Progress and Goals

1:02:32 Connect with Anthony Autry

🎬Watch this on Youtube:

https://youtu.be/CrSTWlfD9xA

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬Produced by:

https://daretopodcast.com/

#DiehardEntrepreneurStories #AnthonyAutry #PurposeDrivenEntrepreneur #LeadershipJourney #MindsetForSuccess #StructuredSuccess #AuthenticLeadership #FromRecoveryToLeadership #CommunityDrivenBusiness #TransformationThroughDiscipline #EntrepreneurMindset #SobrietyAndSuccess #UnchainedFit #GrowthThroughAdversity #BusinessWithImpact #OvercomingObstacles #AccountabilityInAction #PersonalDevelopmentTools #IntentionalLiving #DevinRamosPodcast #MenOnAMission #RecoveryCommunity #FitnessAndMindset #FormerlyIncarceratedLeaders #EntrepreneurStories #ResilientEntrepreneurs #MentalToughnessInBusiness #MindsetMattersMost #BusinessWithPurpose #LeadershipThroughService #ForwardFactor #DevinRamos

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

How Jesse Trujillo Rebuilt His Life After Bankruptcy and Wrongful Imprisonment

In this powerful episode of Diehard Entrepreneur Stories, real estate investor Jesse Trujillo takes us through an emotional and inspiring journey of perseverance, mindset, and redemption. From facing bankruptcy to surviving wrongful imprisonment, Jesse opens up about the darkest moments of his life—and how those moments ultimately fueled his mission to build something meaningful.

Jesse shares how he transitioned from pursuing medicine to real estate, why calculated risks are essential, and how mindset isn’t just important—it’s everything. He reveals the hard-won lessons behind rebuilding after financial collapse, navigating unjust incarceration, and ultimately creating AJX Capital, a company built on values, vision, and a driven team.

This episode dives into the grit required to overcome adversity, the discipline behind smart business moves, and the legacy Jesse is building through service and leadership. If you’ve ever questioned whether you have what it takes to keep going—this conversation is for you.

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

Get on board at: 🤝

https://www.devinramos.com

Connect with Jesse Trujillo:

🌐Invest with Jesse

TIMESTAMPS

00:00 Introduction

02:05 From Medicine to Real Estate

06:52 Lessons Learned from Bankruptcy

08:40 Persistence and Determination

10:36 Balance Being Persistent vs Aggressive

14:42 Risk Management

15:29 Do your Due Diligence and Build Relationships

21:41 The Wrongful Imprisonment: A Life-Altering Experience

27:38 How to Overcame Life’s Toughest Times

29:55 Building Wealth and Helping Others

33:09 The Evolution of Mindset

38:32 Jesse’s Business Journey to Success

43:19 Hiring Challenges and Team Dynamics

47:45 Reflecting on Success and Team Pride

53:28 AJX Capital: Building a Legacy

1:01:26 Jesse’s 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/

#DiehardEntrepreneurStories #RealEstateMindset #ResilientEntrepreneur #FromRockBottomToSuccess #AJXCapital #BusinessWithPurpose #JesseTrujillo #MindsetIsEverything #RealEstateComeback #OvercomingAdversity #LegacyBuilders #FinancialFreedomJourney #HiringWisely #EntrepreneurPodcast #BuildToLast #PurposeDrivenBusiness #DevinRamos #InvestWithJesse #ForwardFactor #DevinRamos

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

What does it really mean to build a business that serves your life—and unlock true freedom?

In this episode of Diehard Entrepreneur Stories, real estate investor and business builder Andy McFarland shares the personal journey and strategic mindset behind creating a business that truly works for you. From flipping his first property (aka “The Treehouse”) to launching multiple ventures, Andy walks us through what it really takes to grow a business that funds both your bank account and your freedom.

Andy talks about the importance of clarity, defining success on your own terms, and building systems that let you step back—not get buried deeper. He shares powerful lessons on letting go, building leaders, and why impact, not hustle, is the real endgame.

We also dive into how Andy has designed his life—intentional travel, family time, and service—all while scaling with purpose. This episode is a reminder that the goal isn’t just more business. It’s more life.

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

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

Connect with Andy McFarland:

📧Email: andymcfarland1980@gmail.com

TIMESTAMP

00:00 Introduction

03:22 Meet Andy McFarland and How He Started in Real Estate

13:25 You Don’t Need External Validation

15:21 The Importance of Mentorship

17:43 Andy’s Spiritual Life & Principles

18:47 The Power of Serving Others

25:30 Impact and Gratitude in Relationships

28:24 Creating Ripples of Impact

31:22 Giving & Receiving Love and Gratitude

33:28 Godfather of Wholesaling: Andy McFarland

36:43 Being a Conduit of Freedom and Money

37:46 Navigating Market Changes and Challenges

42:11 The Birth of a Digital Marketing Company

46:10 Building a Business that RUNS without you

51:41 How to Unlock Time & Financial Freedom

56:18 Personalizing Freedom, Happiness and True Success

1:02:56 Blessed to be a Blessing to Others

1:04:07 Connect with Andy McFarland

🎬Watch this on Youtube:

[We’ll Insert the Link once Published]

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬Produced by:

https://daretopodcast.com/

#TimeFreedomForEntrepreneurs #FinancialFreedomJourney #BusinessThatWorksForYou #RealEstateEntrepreneur #DiehardEntrepreneurStories #EntrepreneurPodcast #FromHustleToFreedom #WorkOnYourBusiness #PassiveIncomeStrategies #BusinessWithPurpose #LegacyOverHustle #FreedomThroughBusiness #SmartScaling #ScaleWithSystems #FlipToFreedom #RealEstateSuccess #EntrepreneurMindset #PurposeDrivenBusiness #DesignYourLife #BusinessGrowthPodcast #FinancialIndependence #AndyMcFarland #ForwardFactor #DevinRamos

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

What’s the one thing even the smartest, most driven people do that quietly sabotages their success?

In this episode of Diehard Entrepreneur Stories, I tackle a mindset killer that holds people back more than they realize: excuses. Whether you're leading a team, growing a business, or trying to level up personally, your ability to own your actions — without justifying them — is what separates those who stay stuck from those who break through.

I share a defining moment from my time in Special Forces training — a single conversation that made me realize the hidden cost of “just giving the reason.” I break down how excuses creep into our thinking, how they influence the feedback loops we’re in, and how to create a culture of accountability without losing compassion.

From military experiences to personal health goals, this episode is packed with real-life examples and practical tools to help you recognize excuses, take ownership, and keep pushing forward.

💡 If you're serious about building yourself, your team, and your business with more clarity, ownership, and action — this one’s for you.

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

Get on board at: 🤝

https://www.devinramos.com

📕Book Mentioned:

Extreme Ownership by Jocko Willink and Leif Babin

TIMESTAMP

00:00 Introduction

02:20 Mindset Shifts from My Green Beret Training Experience

09:41 Reasons vs Excuses

11:10 You Need a Feedback Loop

13:09 Business Bottleneck YOU Need to Overcome

13:50 The Power of Leading with Ownership’

15:35 Observing Without Judgment

17:32 Creating a Culture Where It’s Safe to Fail

18:51 From Excuse to Action: One Step at a Time

25:02 Key Takeaways

🎥Watch on YouTube:

https://youtu.be/asbi_pCmfHo

⚡ Let's stay in touch:

Instagram | Facebook | LinkedIn

🎬Produced by:

https://daretopodcast.com/

#EntrepreneurMindset #ExtremeOwnership #NoExcuses #LeadershipDevelopment #GreenBeretWisdom #SpecialForcesMindset #BusinessGrowthTips #AccountabilityCulture #MindsetMatters #HighPerformanceHabits #SoloPodcast #DiehardEntrepreneur #BusinessWithoutExcuses #TakeOwnership #BreakThroughLimits #SelfLeadership #MilitaryToBusiness #ExcusesKillSuccess #EntrepreneurJourney #ForwardFactor #DevinRamos

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