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Chris Pomerleau built multiple companies, served in the military, passed the bar, and started stacking real estate. From the outside, he had it all figured out. But somewhere along the way, the goalpost kept moving.

In this episode, Ryan and Tanner sit down with Chris to talk about what nobody warns you about on the other side of success. The tension between building and being present. The primal drive to hunt that never shuts off. And the moment his father's final words reframed everything he thought he was working toward.

We get into time blocking, gratitude, teaching kids about money, and why the 3 PM ice cream run with your kids might be the most important meeting on your calendar.

This is not a theory episode. This is a man working through it in real time. Same as you.

The real question this one leaves you with: are you building a life that looks successful, or one you will actually be grateful you lived?

Episode 83 of the Freedom Fighter Podcast with Ryan Miller, Tanner Sherman, and guest Chris Pomerleau.

Follow Ryan on Instagram: @ryanlmillerinvests
Listen on Apple Podcasts, Spotify, and all major platforms.

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Your advisor is lying to you. Not because they're evil. Because their incentives are misaligned with your success.

In this episode, Ryan and Tanner break down why social media real estate doesn't match reality, why grit matters more than hype, and how to find advisors who actually have your back. This is the conversation YouTube's algorithm won't promote but your portfolio needs to hear.

Subscribe for more conversations about faith, freedom, and building a life on your terms.

0:00 - Intro
4:42 - The Instagram vs. Reality Gap
6:55 - First Deal Disasters (The Collapsed Sewer Line)
8:33 - The New Investor Mindset You Need
15:04 - Why Incentives Drive Advice More Than Values Do
16:40 - The Lifetime Value of Integrity
20:27 - How to Find Unbiased Advisors
25:13 - Grit: What It Actually Takes
26:24 - Multiple Exit Strategies (The Real Playbook)
51:30 - Nobody Does It Alone (Ask for Help)
1:02:13 - The W2 Security Myth

Episode 82 of the Freedom Fighter Podcast with Ryan Miller and Tanner

Follow Ryan on Instagram: @ryanlmillerinvests
Listen on Apple Podcasts, Spotify, and all major platforms.

#FreedomFighterPodcast #RyanMiller #FaithAndBusiness #Entrepreneur

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 Comfort can look like success—and still be a cage.

In this episode, we get brutally honest about what happens when we know what God is asking… and we keep negotiating anyway. We talk through a life that looked “winning” on the outside—money, freedom, options—yet felt like slow death on the inside. And we lay out the turning point: the moment pain became mercy, and obedience became the only way forward.

We also put words to the trap most people never see coming: the devil doesn’t always pull you with chaos—sometimes he keeps you comfortable, busy, and numb. We share how discipline (in faith, health, and routine) becomes more than productivity… it becomes protection. Not legalism. Alignment.

You’ll hear how simplifying your inputs—what you consume, think about, and chase—sharpens your ability to hear God clearly. And how building a business without idolizing money changes everything: the way we work, the way we give, and the way we lead our homes. This isn’t a “do more” episode. It’s a “come back to order” episode.

📌 Key Topics:

• Why disobedience can feel like “success” but breed misery ✅
• How pain can become the mercy that wakes us up ✅
• A simple framework for order: God, self, marriage, kids, business ✅
• Hearing God’s voice through daily obedience and fewer distractions ✅
• Health as stewardship: energy, clarity, and discipline that serves your calling ✅
• Tithing and generosity as trust—without treating God like an ROI machine ✅
• Handling criticism without letting comments hijack your mission ✅
  
  
  

Take what we talked about—and choose one clear act of obedience today.

Chapters:

00:00 Meet Tommy and His Journey

01:19 Small Town Roots and Limited Mindset

02:29 Entrepreneur Dreams and Financial Collapse

04:40 Vision of Jesus and Choosing Weed

05:38 Money Without Peace

07:27 Bike Accident Wake Up Call

08:10 Burn the Boats and Move to Vegas

09:37 Comfort as a Devil Trap

14:21 Freedom Through Prayer and Discipline

20:54 Hearing God Through Obedience

28:05 Health Habits and Decision Fatigue

35:05 Kingdom Purpose Over Business Gurus

38:52 Fasting Breakthrough Call

39:48 Romans Tattoo Sign

40:56 God Adds Experts

41:37 Tithing ROI Mindset

43:56 Obedience Over Percent

45:10 Giving 10K Testimony

48:24 Possessions Heart Check

50:37 Investing In Coaching

53:42 Rooms And Alignments

56:30 Stillness And Order

01:00:27 Exhaustion And Delegation

01:03:34 Handling Online Hate

01:11:29 Illogical Faith Steps

01:14:53 Final Thanks And Sendoff

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Sitting on the fence feels safe—until it quietly steals your momentum.

In this episode, we talk about the real cost of slow decisions: missed deals, stressed teams, wasted hours, and the mental drain that makes everything feel heavier than it needs to be. Decision fatigue isn’t just a productivity issue—it’s a leadership issue.

We share what’s changed for us over the last several months: we’re making calls faster, fixing problems faster, and moving on without dragging the “who’s at fault” conversation behind us. We walk through a real example—an employee pay mistake—and how a two-minute, decisive response protected trust, preserved culture, and solved the problem immediately.

But we also challenge the idea that “fast” means reckless. Some decisions need urgency. Others need timing. The win is knowing the difference—then acting without hesitation.

We zoom out into the deeper layer: why people freeze in the first place. Fear of being wrong. Fear of regret. Fear of choosing the “bad” option. Our takeaway? You don’t need 100% certainty—you need forward motion. Commit 10%, get data, adjust early, and avoid the trap of overcommitting to the wrong path.

We also get practical: reduce micro-decisions so you have energy for the big ones—systems for meals, groceries, calendars, routines, and KPIs. Less noise. More clarity. More freedom.

📌 Key Topics:

• Decision fatigue and why “no” becomes the default when we’re tired ✅
• Fixing problems fast without wasting time on blame ✅
• The 10% commitment rule: move, test, correct early ✅
• Saying “no” faster to get to the right “yes” sooner ✅
• Building simple systems that remove daily decision clutter ✅
• Why momentum beats perfection—every time ✅
  
  
  

Ask yourself: where are you still “thinking” when you should be choosing—and what would change if you decided today?

Chapters:
00:00 Fixing the Hook: Stop Over-Explaining at the Start

00:33 Um’s, Ah’s & the Transcript Wake-Up Call

01:16 Decision Fatigue: The Real Skill They’ve Improved

02:13 Payroll Mistake Case Study: Decide Fast, Fix Faster

05:37 When NOT to Rush: Timing Decisions Like a Pro

06:44 Jocko’s 10% Rule: Commit Small, Adjust Quickly

08:07 Atomic Habits Momentum: Small Steps That Compound

10:25 Decision Fatigue Science: Parole Board & Morning Decisions

11:48 The Fence Is Mine: Faith Analogy for Indecision

12:59 Leaning Into Fear: Saying Yes to the First Podcast

14:22 The Butterfly Effect: How One ‘Yes’ Changed the Podcast

16:09 Say ‘No’ Faster: Filtering Bad Deals & Avoiding Analysis Paralysis

16:56 Real-World Example: Quick Offer, Quick Walk-Away

18:11 Yes vs No: The Numbers Game (VC Logic & Underwriting Muscle)

21:35 Why We Freeze: Decision Psychology, Fence-Sitting & the Fork in the Road

23:35 Decision Fatigue Hacks: Uniforms, Calendars & Pre-Deciding Your Year

25:08 Systems That Save Hours: Instacart, Meal Planning & Grocery Store Traps

28:47 Final Challenge: Make the Next Decision Faster

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Freedom isn’t a vibe — it’s built with responsibility, preparedness, and real relationships.

In this episode, we sit down with a firefighter-paramedic and small business owner who reminds us what “service” actually looks like when it’s not a slogan. We talk about why firefighters aren’t just “firefighters” (fires are a tiny fraction of the calls), and what it takes to stay calm when everyone else is panicking.

But the conversation goes deeper than emergency scenes.

We unpack why so many first responders can’t sit still — why they build side businesses, work with their hands, and feel restless in a world that’s gone fully digital. We get honest about the mental cost of living at a high level of readiness… and why the answer isn’t more noise, more hustle, or more tech. It’s accountability. Community. The kind of handshake integrity that’s disappearing fast.

We also talk about building a security company the right way — paying people a living wage, training them well, doing the “boring” due diligence (insurance, liability, real standards), and refusing to treat clients like numbers. Because “Jerry” isn’t an invoice… he’s a family, a payroll, a livelihood — and protection means understanding the whole chain.

And if you’re a parent? You’ll walk away with practical preparedness habits you can implement this month — not fear, just track-laying before life hits.

📌 Key Topics:

• What firefighters really do (and why fires are the minority) ✅
• Why some people think best under pressure — and what it costs later ✅
• Building a business with personal connection in an AI world ✅
• Security done right: training, wages, liability, and integrity ✅
• Simple family preparedness rhythms that actually save lives ✅
• Why freedom is local — and why it always comes with responsibility ✅
  
  
  

Take what we talked about and ask yourself: What would change this week if we treated freedom like something we build — not something we post about?

Chapters:

00:00 Meet Nick and His Story

00:22 From College to Fire Service

01:43 EMT Training and Getting Hired

02:40 What Firefighters Really Do

05:29 Thriving Under Pressure

08:55 Why Firefighters Build Businesses

11:30 Firehouse Culture and Accountability

15:24 Starting Elite Tactical Security

18:51 Growing People Not Just Profit

21:26 Staying Small and Personal

27:44 Systems to Stay Connected

31:30 Unoffendable and Clear Communication

35:03 Situational Awareness and Preparedness

39:33 Men Women and Team Balance

43:36 Selling With Empathy

44:15 Fire Alarm Partner Roles

46:29 Choosing The Right Partner

48:45 Working With Your Spouse

51:38 Why Start A Security Firm

52:40 Nebraska Security Oversight Gap

55:06 Cheap Security Real Risks

01:00:45 Accountability Over Greed

01:03:01 Home Fire Safety Routine

01:05:17 Smoke Detectors And Batteries

01:07:52 Car Seat Help And Liability

01:10:50 Freedom And Community

01:13:14 How To Connect And Wrap Up

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ChatGPT isn’t “AI.” It’s just the brand most of us started with.

In this episode, we get real about what happens when you stop treating AI like a chatbot… and start treating it like infrastructure. We share why we moved beyond ChatGPT, what surprised us about Claude, and how “scaffolding” (the 90% behind the scenes) is what turns AI from a toy into a tool that can actually run parts of your business.

We talk about building a personal “Jarvis” that doesn’t just answer questions—it pulls numbers, flags blind spots, organizes decisions, and gives you an owner-level snapshot in seconds. Not theory. Real workflows: email triage, calendar handling, dashboards that unify QuickBooks + ops + marketing, and a simple prompt that might change how you think forever: “Show me my blind spots.”

We also hit the part most people ignore: security. If you’re handing AI the keys to your life, you better know what doors you just unlocked. The goal isn’t replacing people—it’s freeing your team to do higher-level work while you make faster, cleaner decisions.

📌 Key Topics:

• Building AI “scaffolding” so it knows where to pull truth from ✅
• Turning scattered tools into one decision dashboard ✅
• Using AI to expose blind spots before they cost you ✅
• Security red flags when AI touches email, browser, and finances ✅
• Starting with your biggest bottleneck—not the coolest feature ✅

If you want more freedom, stop chasing hacks—and start building systems you can trust.

Chapters:
00:00 Why I Quit ChatGPT (and 10x’d My Business)

00:28 Testing ChatGPT vs Gemini vs Claude — What Actually Worked

02:03 The Vegas Story: SamCart CEO Rebuilt a Business in 45 Minutes

04:28 Claude vs ChatGPT Personalities + Better Strategic Output

06:01 My #1 AI Prompt: “Show Me My Blind Spots”

06:51 The Real Secret: “Scaffolding” Your AI Like an Operating System

08:34 Going Phone-First: Running My AI Assistant on WhatsApp

10:12 Modern-Day Jarvis: $20 vs $200 Claude Plans (Credits & Opus Access)

13:26 How I ‘Train’ It: Claude Code, Iteration, and Commander's Intent

14:36 Building the Unified Business Dashboard (QuickBooks + Ops + Marketing)

15:58 One Assistant, Multiple Businesses: Consolidating Data into One Database

16:51 Using Other AIs as Sub-Agents: ChatGPT for Research, Gemini for YouTube

18:35 Security & Risk: Giving an AI Access to Your Browser and Financial Data

20:35 Security & privacy concerns with AI assistants

21:15 AI won’t kill the assistant role— it upgrades it

21:58 Real example: offloading email/calendar while upskilling the team

23:15 What’s next for the custom dashboard (voice, WhatsApp, team access)

26:25 Why most owners don’t build this (and what it could be worth)

28:15 Where to start: bottleneck analysis + using AI for financial clarity

29:21 QuickBooks reality check: bank feeds, reporting gaps, and security limits

30:58 Can AI replace bookkeepers? Trust, accuracy, and human oversight

32:13 Using AI for strategy: frameworks, coaching, and what humans still do best

35:32 The real power of dashboards: tying metrics to behavior and revenue

37:08 Building it in-house: replacing scattered tools and saving $5k/month

40:13 Closing thoughts & a meta-AI idea for analyzing the podcast

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In this episode, we dive into the "unknown unknowns" of entrepreneurship—the problems you don't see coming until they hit you. From QuickBooks payroll nightmares and duplicate W2 filings to the surprising workarounds for renting a car with a debit card, we share real-world solutions to the challenges that every business owner faces.

We also unpack the myth of linear business growth. Why do some businesses scale 10X while others get stuck? We discuss the power of "who not how," the importance of getting in the right rooms, and how to cultivate a mindset that embraces million-dollar problems as a sign of success.

00:00 Introduction and QuickBooks Troubles

00:29 Unexpected Business Challenges

01:22 Dealing with Payroll and Bookkeeping

09:06 Scaling and Business Growth

14:42 Masterminds and Networking

32:07 The Importance of Community

32:36 Conclusion

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How to Build a 7-Figure Real Estate Portfolio From Scratch

In this episode, we sit down with Josh, a real estate investor who made the incredible journey from a dream job in corporate sales at Oakley and Trek Bikes to building a thriving real estate business.

Josh shares the raw, unfiltered story of why he walked away from a successful career in the action sports industry to pursue financial freedom through real estate investing. We dive deep into the mindset shifts, the challenges of starting over, and the critical role his faith has played in his success.

📌 Key Topics:

• ✅ The exact moment to leave a W2—and the safety nets to stack first
• ✅ Our three-option framework for sellers: retail, real cash, or creative terms
• ✅ How to use subject-to/seller finance ethically (and where it goes wrong)
• ✅ Building real deal flow through community, not cold DMs
• ✅ Intrinsic drive vs. borrowed motivation—and how to self-govern daily
• ✅ Bringing faith and integrity into business without being weird
• ✅ A practical, boring definition of freedom that actually holds up

Chapters:

00:00 Introduction and Initial Real Estate Deal
00:14 Career Struggles and Turning Point
00:24 Discovering Real Estate
00:52 Podcast Introduction and Guest Background
02:51 College Years and Early Career
11:27 Transition to Real Estate
19:27 Applying Past Skills to Real Estate
28:04 Faith and Business Integration
37:31 Navigating Community and Belonging
37:45 Challenges in Building Community in Santa Cruz
39:52 Marriage Counseling and Community Loss
40:48 Moving to Omaha and Building New Communities
42:16 The Sub Two Community and Real Estate Networking
45:24 Intentional Networking and Business Growth
57:22 Creative Financing in Real Estate
01:02:20 Risks and Protections in Subject To Deals
01:07:16 The Value of Community and Mentorship
01:13:22 Defining Freedom and Personal Goals
01:15:42 Closing Thoughts and Contact Information