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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

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Why does the news prioritize chaos over clarity? A look at how media incentives, funding, and logical fallacies shape our perception of civil unrest.

In this episode, we examine the shifting dynamics of civil unrest, drawing parallels between the Minnesota George Floyd riots and current events. We explore the logistical evolution of activism, specifically how organized funding and "flying in" protesters can transform a peaceful gathering into urban chaos. By analyzing the media incentives that favor fear-mongering and polarization over objective truth, we discuss how business owners and leaders can navigate a landscape of misaligned incentives and "brain rot" content.

The conversation shifts toward practical solutions for reclaiming intellectual independence. We break down the grassroots level impact of critical thinking skills and the importance of recognizing logical fallacies like the straw man or slippery slope in political discourse. Whether you are a parent looking into the homeschool movement or a professional striving for entrepreneurial freedom, this episode provides a roadmap for filtering out the noise, avoiding confirmation bias, and focusing on what you can actually control.

Chapters:
0:00 Comparing the Minnesota Riots to Current Unrest
2:15 How Activist Groups Fund and Mobilize Protests
4:42 Media Incentives: Why News Outlets Prioritize Polarization
7:10 The Dangers of Headline Culture and Misinformation
10:05 Statistics vs. Sentiment: Is the World Actually Getting Safer?
13:22 Balancing Global Awareness with Local Responsibility
16:45 Grassroots Solutions: Cultivating Critical Thinking Skills
19:15 Breaking Down Common Logical Fallacies in Politics
22:30 Parenting and Teaching Debate at a Younger Age
25:50 Leadership Lessons: Avoiding the "Borrowing Authority" Trap
29:10 Taking Control: Building Personal Freedom in a Chaotic World

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The right mindset can turn a lost start into a life you’re proud to lead—and we show you how in this conversation.

We sit down with a first-gen immigrant, Marine veteran, and now independent insurance agency owner to unpack what it really takes to build freedom—personally and professionally. From a small Nebraska town to Afghanistan to launching a relationship-driven brokerage, we get specific about the habits, leadership moves, and systems that actually compound.

You’ll hear how military discipline became “life’s Adderall,” why the independent model is beating the big brands, and how to scale without losing your soul. We get honest about divorces, resets, hiring young talent, and building a team that holds each other accountable at one big sales table—no ivory towers, just real work.

We also pressure-test the future: AI’s role in service businesses, what should be automated (and what never will), and how to protect the human edge—trust, speed, and genuine relationships. Along the way we talk generational progress, immigrant grit, and the quiet power of podcasting to build real partnerships.

📌 Key Topics:
✅ From Marine Corps lessons to leading a civilian team with clarity and trust
✅ Why independent insurance is winning—and the real economics behind it
✅ Turning “big goals” into daily actions with backward planning and accountability
✅ Balancing tradition and innovation so tech speeds you up, not thins you out
✅ Hiring for character, coaching for skill, and letting people learn by doing
✅ Mindset shifts that create freedom: discipline, consistency, and earned confidence
✅ The future of AI in service industries—and how to keep the human advantage
✅ Relationships as a strategy: lending, real estate, podcasting, and community

Listen in, then pick one system, one habit, or one relationship to strengthen this week—and watch your freedom compound.

Chapters:

00:00 Introduction and Guest Background

00:28 Early Life and Joining the Military

02:01 Military Experience and Personal Growth

03:49 Transition to Civilian Life and Insurance Career

06:02 Building an Independent Insurance Agency

08:16 Challenges and Strategies in the Insurance Industry

18:28 Leadership and Team Development

20:59 Applying Military Lessons to Business

33:37 Reflections on Life and Generational Progress

35:52 The Immigrant Experience and Entrepreneurship

37:51 Challenges and Realities of the Insurance Industry

43:16 The Importance of Mindset and Hard Work

47:23 Balancing Tradition and Innovation in Business

52:44 The Future of AI and Its Impact on Industries

01:02:32 The Value of Relationships and Personal Connections

01:04:10 Podcasting and Learning from Experts

01:05:03 Final Thoughts and Consistency in Success

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Real estate isn’t a lottery ticket—it’s a system. In this episode, we unpack our five-pillar “Sherman Strategy” so you can invest with purpose in 2026 and beyond.

We get practical about where your time, money, and risk actually belong. Mindset comes first—becoming the kind of person who learns, shows up, and builds habits. Then we stress-test motives (relationships), map the money (financial), choose your lane (growth), and protect the wins (sustainability). No gurus. No one-size-fits-all. Just a framework you can tailor to your life stage and risk profile.

You’ll hear real scenarios: the single house-hacker turning a triplex into equity, the teacher who leveraged a HELOC into five doors and a plan, and the family shifting paid-off coastal homes into Midwestern apartments for steadier appreciation. We talk velocity of money vs. safety, short-term gains vs. long-term holds, and why recovering seed capital changes the game. We also clear up common myths—FHA/VA occupancy rules, passive “set it and forget it” promises, and the trap of saving small forever.

📌 Key Topics:
✅ The 5 Pillars: Mindset, Relationships, Financial, Growth, Sustainability
✅ Growth vs. Sustain: risk profiles, leverage, and the goal of recovering seed capital
✅ House hacking, BRRRR timing, and when to refinance (or not)
✅ Using HELOCs responsibly—and how to “graduate” to bigger deals
✅ Tax plays: bonus depreciation, short-term rental loophole basics
✅ Exit plans that survive real life (vacancies, repairs, market shifts)
✅ Why specialist brokers beat generalists for niche assets

We’re here to help you stop guessing, pick a clear path, and move with conviction. Ask yourself: which pillar needs attention this week—and what’s the next right step you’ll take to build freedom on purpose?

Chapters:

00:00 Introduction to the Sherman Strategy

00:48 The Five Pillars Framework

01:21 Mindset and Relational Pillars

02:45 Financial and Growth Pillars

04:09 Sustainability and Risk Profiles

06:26 Custom Strategies for Different Investors

07:05 Case Studies and Real-Life Examples

09:00 Investment Strategies and Market Timing

15:53 Legal Considerations and Mortgage Fraud

19:49 Tailoring Strategies to Individual Goals

28:24 Risk Profiles and Investment Velocity

29:55 The Power of Leverage in Real Estate

30:40 Misconceptions About Offsetting Income with Real Estate

31:39 Tax Savings and Growth Strategies

33:00 Customizing Real Estate Strategies

35:15 Real Estate Investment for Young Adults

36:58 Balancing Risk and Reward in Real Estate

40:39 Growth vs. Sustainment Strategies

54:39 Specialization in Real Estate Investments

56:40 Conclusion and Final Thoughts

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What if the one decision you’re avoiding is the key to your next season of freedom?

This week we sit down with our business coach and pull back the curtain—on coaching that actually changes Monday, not just your mood on Friday. We get real about pricing, permission, and why accountability beats inspiration 10 out of 10 times. We unpack the “one thing” approach, the Visionary vs. Integrator puzzle, and how to build momentum with small wins that knock over bigger dominoes.

You’ll hear the messy, human parts too—marriage, money, calling, and the tension between helping people and “eating and living indoors.” We share the simple guardrails that keep you out of the ditch, the leadership law of “no surprises,” and the faith-and-focus mindset that lets you sleep at night because you served people well.

If you’re on the fence about coaching, or you’re leading alone and tired of guessing, this conversation gives you a clear, practical path: what to measure, when to ask for help, and how to turn knowledge into results with daily action.

📌 Key Topics:
• Accountability that pays for itself—how we structure it ✅
• Finding your “one thing” and stacking wins (the domino effect) ✅
• Visionary vs. Integrator: who you are vs. where you’re most useful ✅
• Pricing, permission, and the real ROI of coaching ✅
• The “No Surprises” leadership law and psychological safety ✅
• Tools that matter (big calendar, tight rhythms, human resources) ✅
• When to hire a coach—and when an accountability stake is enough ✅
• Freedom as removing weight vests, not adding hacks ✅

Listen in, pick your one thing, and take one bold step today you’ll thank yourself for in a year.

Chapters:

00:00 Introduction and Welcome

00:52 Michael's Journey to Omaha

01:49 Meeting Jessica and Moving to California

05:04 Transition to Business Coaching

07:10 Challenges and Rewards of Coaching

12:00 Balancing Business and Personal Life

17:34 The Importance of Accountability

42:04 Finding Your One Thing

44:43 Tanner's Vision and Aspirations

45:21 Building Momentum with Small Wins

46:13 The Domino Effect and Achieving Goals

52:25 Visionaries vs. Integrators

53:23 The Importance of Passion in Leadership

01:02:54 Tools and Resources for Success

01:05:47 The Role of Coaching and Mentorship

01:06:54 The Value of Human Resources

01:14:00 Freedom and Removing Obstacles

01:15:54 The Right Time to Hire a Coach

01:24:08 Michael Owen's Contact Information and Final Thoughts

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Goals don’t change us—identity does.

Most of us set big targets, get hyped, then fall off by January 20th and feel like quitters. In this episode, we get painfully honest about why that happens and how to build the kind of life that lasts. We replace “set a goal” with Be → Do → Have: become the person first, take the smallest daily action next, and let the results follow.

We talk about identity over resolutions, grace without excuses, and the simple rule that saves momentum: no two days lost. If you’re working hard and going nowhere, this is your reset—less pressure, more progress, and a faith-first lens for leading your home, work, and money.
We get practical: tiny habits that actually stick, how to measure what matters (leading measures, not vanity metrics), and a simple decision filter to buy back time and income—no more “either/or” traps. We also share how to think like an investor before you own a single asset and why consistency beats “perfect” every time.

📌 Key Topics:
✅ Identity beats resolutions (Be → Do → Have)
✅ No two days lost: stack wins, never break the chain
✅ Do less but daily: small steps, compound outcomes
✅ Leading measures only: track what moves the needle
✅ Investor before investments: act the part, then own the part
✅ And, not or: buy time and results
✅ People before profits; time over money; faith over hustle

If you’re stuck, tired, or behind, choose the next right move today—then repeat it tomorrow.

Chapters:
00:00 Why New Year's Resolutions Fail
01:30 The Be-Do-Have Framework
02:21 Identity-Based Goals
04:05 Simplifying SMART Goals
06:17 The Importance of Small Steps
09:06 Consistency and Habit Stacking
14:03 Setting Business Goals
18:01 Balancing Time and Money in Business
27:43 Understanding Fixed Costs and Margins
28:46 The Importance of Tracking Metrics in Real Estate
29:45 The Truth About Numbers and Context
31:59 Setting and Achieving Personal Goals
34:11 Biblical Context of Goal Setting
36:03 First Principles and Goal Setting
37:01 Balancing Personal and Professional Goals
39:38 The Importance of Intentionality
43:41 Consistency and Habit Stacking
48:44 Final Thoughts on Goal Setting and Improvement