Gary's Gulch
Our Founding Fathers gave us simple guidelines for protecting our lives, liberty, property, and finances. As a society it’s time for us to get back to becoming producers, not takers. This call to freedom is to lead our families and communities to a better future. Inspired by Ayn Rand's Atlas Shrugged, Gary's Gulch is for lifelong learners. Liberty seekers. Energized people like you, driven to make YOUR world a better, more productive place – If you are prone to blaming others for your lot in life, or expect another to fix your situation, this podcast is NOT for you. Topics include family, legacy, small business, investments, education and personal finances. Your show host is veteran Navy Captain Gary Pinkerton, an accomplished Naval submarine commander and advisor who is guiding families across the country to achieve this mission – Mastering and sharing Unique Genius. Now is the time to bolster our freedoms and produce value; to create a stronger Nation and brighter tomorrow.
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Investment Education and Opportunities with Dani Lynn Robison founder of Freedom Family Academy
12/23/2025
Investment Education and Opportunities with Dani Lynn Robison founder of Freedom Family Academy
Summary 🎙️ Tune in to Gary's Gulch for a festive episode featuring Dani Lynn Robison from Freedom Family Investments. Discover how Dani transitioned from music to real estate, the power of education, and practical insights on safer investing. Dive into the launch of the Freedom Family Academy—a hub for financial education and trust. Perfect for those eager to invest wisely in 2026! 🎄💼 #RealEstate #InvestSmart. Episode Highlights 01:21 - Reflection on a Better World 03:32- Control in Investing 04:37 - 10 Commandments of Investing 06:04 - Education: College vs. College of Life 07:33 - Hands-on Learning in Real Estate 10:55 - Starting in Real Estate During 2008 13:12 - Learning From Bad Deals 14:10 - Vetting Real Estate Partners 16:32 - Worst Deal Experiences 19:55 - Character in Challenging Times 21:10 - Who Do You Trust? 22:23 - Freedom Family Academy Overview 24:18 - Vision for Freedom Family Academy 27:13 - Importance of Education and Trust 30:10 - Financial Freedom and Liquidity 32:18 - Advisory Board and Education Network Episode Resources Connect with Gary Pinkerton Keywords Gary's Gulch Merry Christmas financial situation anniversary celebration 250th year positive change connection with Savior make the world better invest safely financial control 10 Commandments of Investing Freedom Family Investments Freedom Family Academy Board of advisors syndication real estate investment hierarchy of wealth investment education experience learning property tours multifamily residential investment risk due diligence character of people passive income trustworthiness promissory notes annual liquidity recession resistant real estate workforce housing senior housing self storage Board of Advisors CPAs, attorneys, tax, insurance, estate planning education first Freedom Family Academy investment journey financial freedom personal assets Gary's clients real estate syndication investor education Freedom in real estate investment opportunities Connect with Gary Pinkerton Keywords Gary's Gulch Merry Christmas financial situation anniversary celebration 250th year positive change connection with Savior make the world better invest safely financial control 10 Commandments of Investing Freedom Family Investments Freedom Family Academy Board of advisors syndication real estate investment hierarchy of wealth investment education experience learning property tours multifamily residential investment risk due diligence character of people passive income trustworthiness promissory notes annual liquidity recession resistant real estate workforce housing senior housing self storage Board of Advisors CPAs, attorneys, tax, insurance, estate planning education first Freedom Family Academy investment journey financial freedom personal assets Gary's clients real estate syndication investor education Freedom in real estate investment opportunities Connect with Gary Pinkerton Keywords Gary's Gulch Merry Christmas financial situation anniversary celebration 250th year positive change connection with Savior make the world better invest safely financial control 10 Commandments of Investing Freedom Family Investments Freedom Family Academy Board of advisors syndication real estate investment hierarchy of wealth investment education experience learning property tours multifamily residential investment risk due diligence character of people passive income trustworthiness promissory notes annual liquidity recession resistant real estate workforce housing senior housing self storage Board of Advisors CPAs, attorneys, tax, insurance, estate planning education first Freedom Family Academy investment journey financial freedom personal assets Gary's clients real estate syndication investor education Freedom in real estate investment opportunities
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Why the Fire at my Rental Property is a Good Thing!
12/19/2025
Why the Fire at my Rental Property is a Good Thing!
Summary In this episode, Gary Skelts navigates a real estate setback as one of his properties in Memphis catches fire. While many would see disaster, Gary highlights the importance of active involvement in business, viewing this challenge as a learning opportunity. Explore leadership, risk, and why passive income can't replace active engagement. This conversation is a must-listen for those invested in real estate or contemplating the realities of passive income.. Episode Highlights 00:00:40 Turning real estate headaches into opportunities. 00:02:20 - Active business vs passive real estate. 00:03:32 - Delegation and leadership lessons. 00:05:23 - Real estate as a storehouse of wealth. 00:07:19 - Hard assets and inflation. 00:09:02 - The role of a bookkeeper in real estate management. 00:11:11 - Learning from property management and insurance testing. 00:12:16 - Executing property management decisions wisely. 00:16:02 - Insights on handling property challenges. 00:18:21 - Learning from setbacks for future growth. Episode Resources The podcast transcript does not provide any specific mentions of books, websites, or tools that can be linked. It mainly contains discussions about personal experiences, property management, and real estate investment strategies, but does not refer to specific resources by name or URL. Keywords real estate property management passive income investment strategy financial independence insurance claims property maintenance fire damage rehabbing properties leadership bookkeeping wealth storage hard assets inflation income properties real estate portfolio turnkey properties fire movement rental income property management challenges
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Business Ownership Always Trumps Real Estate Investing
12/12/2025
Business Ownership Always Trumps Real Estate Investing
In this episode I discuss the misconception that passive investing in real estate or in anything else is not a business; active participation in real estate is a business which just happens to be in the real estate industry. Gaining skills in how to run a business are incredibly beneficial to improving your Control, Mindset, Agency, and Legacy - marketing, sales, leadership, financials, taxes, innovation are truly valuable to learn and teach those that come behind you. AND they are essential to maintaining America and the world free for future generations. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Intro to the 2026 Freedom Series, Importance of Business Ownership
12/04/2025
Intro to the 2026 Freedom Series, Importance of Business Ownership
2026 on Gary's Gulch podcast will be dedicated to celebrating our 250th anniversary of the Great American Experiment - If you give citizens ownership over their life, liberty and property and design a government made up of the people and working for the people, they will prosper. Business ownership is fundamental to this premise. Nearly everyone in 1776 was a business owner, there was a need in the community and someone started a business to serve that need. We've gotten away from this with the industrial revolution and globalization (someone in China fills your need via Amazon). We must get back to honoring the value of businesses. Listen in to learn what's coming in '26! Highlights 02:19 - Importance of freedom and personal agency. 04:49 - Divine guidance vs. worldly advice. 06:14 - Real estate vs. gold and silver. 07:52 - Scaling businesses vs. traditional wealth growth. 09:58 - Unique genius and business creation. 11:44 - Historical perspective on business ownership and community value. 12:08 - Critique of modern political figures and ethics. 13:55 - Lessons from early American settlers. 15:20 - Business ownership as a pathway to agency and legacy. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Jen McAllister, founder of Rise CPAs and Accountants - Bringing Huge Value to your Business
11/25/2025
Jen McAllister, founder of Rise CPAs and Accountants - Bringing Huge Value to your Business
As promised in the last episode, I turn the tables on my client and fellow business owner Jen McAllister to explain how her team of CPAs and Accountants deliver everything for small to medium sized businesses. She's passionate about helping businesses clean up the books, get more tax efficient and grow. Listen in to see if this tremendous team is right for your business. Highlights Preparing assets for sale Value by strategic design The role of family and business in the U.S. Evolving with client needs Year-round business immersion Bookkeeping vs. strategy Financials: not just numbers When to bring in external help Scaling with flexible teams The importance of exit planning Helping businesses grow up Maintaining quality of life in ownership Hiring strategically for growth Links and Resources from this Episode Connect with Gary Pinkerton Connect with Jen McAllister Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Tools for Successful Business and Legacy with Jen McAllister
11/18/2025
Tools for Successful Business and Legacy with Jen McAllister
This is part 2 in a series on creating successful family businesses and legacy. The last episode laid out why it is important. This episode introduces how to do it, what tools help my clients as their guide towards a successful family wealth, agency and legacy. Highlights Elon Musk’s vision for the future. Importance of a strong family unit. Elon Musk and leadership decisions. Infinite Banking and legacy tools. New challenges for business owners. Becoming a certified exit planning advisor. The importance of owning your expertise. Turning a Ponzi scheme failure into strength. Value of admitting mistakes quickly. Key message: Invest in yourself. Links and Resources from this Episode Connect with Gary Pinkerton Connect with Jen McAllister Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Focusing on Family and Business is the Key to Defeating Evil
11/11/2025
Focusing on Family and Business is the Key to Defeating Evil
Many were shocked when a hardcore socialist was elected mayor of NY City, the symbol of financial strength and the successful American experiment. How do we save America and the world? Agency, of course - but it is deeper than we've discussed before - listen in to this first of a two-part series on the importance of strong nuclear families and the American business owner hear why! Highlights Agency as personal freedom. Historical perspective on individual rights. Current societal and political challenges. The power shift: weak people creating hard times. Predicting a return to better times. Personal empowerment through business ownership. The importance of gratitude and humility. Remaining connected to a higher power. Dangers of ego and disconnection from spirituality. Family’s role in sustained freedom. Business ownership as a conduit for personal expression. Introducing future tools for business success. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Family Banking and Legacy with Jaden Zubal
11/06/2025
Family Banking and Legacy with Jaden Zubal
This is the audio recording of a webinar I produced with Jaden Zubal recently for our combined audiences. We discuss how we help business owners, Real Estate Investors and those looking to leave a financial and cultural legacy for their future generations or a cause they are passionate about sustaining long after they are gone. Links and Resources from this Episode Connect with Gary Pinkerton Connect with Jaden Zubal Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Rentals and the Economy with Aaron Chapman
10/21/2025
Rentals and the Economy with Aaron Chapman
I welcome back to Gary's Gulch close friend and expert mortgage lender Aaron Chapman to discuss recent changes in interest rates, inflation and the threat of new quantitative easing. What does it all mean and how do you protect your retirement, your family and your legacy? And as a bonus, we give a preview to an incredible personal growth experience we're launching in the Ozark mountains in 2026. Links and Resources from this Episode Connect with Gary Pinkerton Connect with Aaron Chapman Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Demystifying Trusts and what you need to do NOW
10/17/2025
Demystifying Trusts and what you need to do NOW
Most of my clients are confused, frustrated and frankly misled on this involved topic. Attorneys have the tendency to want to show the breadth of their knowledge and that is a big disservice to individuals trying to navigate all the options and features available in this broad topic of Trusts. This is a really important topic that many families put off unnecessarily and take big financial risk in doing so - listen in and let's take this worry off the table with concrete steps you can easily take. Highlights 1% of financial advisors struggle with trust knowledge. Types of trusts. Three key aspects of trusts. Revocable vs irrevocable trusts. Purpose of revocable living trusts. Avoiding probate with a trust. Control from the grave. When a trust becomes irrevocable. Importance of asset protection. Tax implications of irrevocable trusts. The role of domestic asset protection trusts. Income tax implications for trusts. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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30 Year Mortgage - the Best choice backed by the Math
09/30/2025
30 Year Mortgage - the Best choice backed by the Math
The Fed finally lowered interest rates and the mortgage companies are relentlessly pushing for refinances. What is the best choice? In almost all cases, it is the 30 year fixed. Why? Many reasons - listen in and find out! Highlights Fed lowers interest rates: Mortgage opportunities. Velocity banking: An Australian trick. Bet on yourself: God-driven decisions. 15-year vs 30-year mortgages: Initial setup. Payment calculations: Mortgage comparison. 15-year mortgage interest: Quick payoff impact. Cash vs mortgage: Wealth building scenarios. Million-dollar example: Time as a financial factor. Tax misconceptions: Understanding tax brackets. Inflation impact on mortgages: Long-term effects. Financial strategies: Tax and deduction insights. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Lower Rates, Prophets and Celebrating the Wins
09/26/2025
Lower Rates, Prophets and Celebrating the Wins
September 2025 has been a whirlwind of change and unprecedented events. The Fed finally lowered rates, the economy is booming, there is a revival of goodness in our country and the world. It is time to celebrate the wins! Highlights Clarification: Prophets vs. Profits. Charlie Kirk’s legacy and impact. Handling triggers and emotional responses. Responding vs. reacting - Zig Ziglar’s insight. Focusing on gratitude to avoid being triggered. Good vs. Evil: A testament to God’s existence. Erica Kirk’s forgiveness at Charlie Kirk’s memorial. Current events: Federal Reserve rate changes. Personal journey: From negative net worth to financial success. Lessons from financial journey and business ownership. Gratitude as a counter to negativity and triggers. Optimism for revival of goodness in the world. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Why invest and How to Optimize every Dollar
09/12/2025
Why invest and How to Optimize every Dollar
Most people do very little strategic thinking about what investments they have or why they have them. They simply follow the herd or a popular investment newsletter that promises huge returns. In this episode I explain why residential rental properties are a cornerstone of my investment strategy and why I recommend you consider them as well. I get into specifically why I support these investments with infinite banking or family banking life insurance policies and show a couple of examples of the financial impact of doing so. Highlights Why rental properties and hard assets? Impact of overall portfolio on wealth returns. Infinite banking: explanation and personal impact. Lessons from a rural upbringing and stagflation. Navy career and financial wake-up call. Control over money equals reduced risk. Maslow’s hierarchy of needs applied to investments. Direct vs. indirect investment risk. Differences between savings and investments. Borrowing against life insurance for investments. Infinite banking’s financial advantage demonstration. Differences in returns with infinite banking. Constructing an infinite banking policy. Whole life insurance vs. IUL and its implications. Accessing and contributing flexibility to policies. Scalability and contribution duration in policies. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Liquidity is Your Super Power!
08/26/2025
Liquidity is Your Super Power!
I constantly get questions and push-back on holding so much of my client's net worth as liquidity in their Hierarchy of Wealth's Tier 1 foundation layer. This episode digs into things we've heard like Cash is Trash so that business owners, real estate investors and those managing their family finances can put into perspective the value of liquidity and looking holistically at their Return on Wealth, not just microscopically at one investment they made or another. Bottom line - liquidity is king, it is food for the racehorse, and if you are seeking greater agency in your life then You are that horse! Highlights Liquidity as a superpower. Feeding the racehorse analogy. Marketing during recessions: A turnaround strategy. Crisis and opportunity: The same symbol fallacy. The importance of having a war chest. Debunking “cash is trash” misconception. The redundancy analogy from nuclear power. Return on wealth concept introduced. Overcoming fear of missing out. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Is it bad enough yet? Excellence means acting before it is
08/19/2025
Is it bad enough yet? Excellence means acting before it is
One of my heroes and a great Patriot, Dan Bongino would ask this repeatedly on his podcast and radio show before he accepted the position as 2nd in charge at the FBI. When people constantly endured incremental losses of freedom and agency, he would point out that is simply wasn't bad enough for them to put a stop to it yet. How do we avoid this cycle of pain and change beforehand? I've got some thoughts, listen in! Highlights Question to the audience: Facing life challenges? Insight from Russell Brand on life difficulties. Personal struggle with faith and surrendering to God. Realization of ego in personal struggles. Approach to prayer and trusting God. New path and unexpected opportunities. Emphasis on family time and personal reflection. Approach to client meetings: quarterly calibration. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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If life is constantly hard, YOU are doing it to Yourself!
08/12/2025
If life is constantly hard, YOU are doing it to Yourself!
Gary explores the power of surrendering to divine guidance in overcoming life’s challenges. Reflecting on a compelling conversation between Charlie Kirk and Russell Brand, Gary discusses how ego often stands in the way of truly listening to what God wants. This episode is a thoughtful reminder that leaning on faith and acknowledging moments of divine intervention can help navigate life’s complexities. Perfect for listeners seeking encouragement and a deeper understanding of faith in everyday struggles. Highlights Personal struggle and life’s challenges. Russell Brand’s influence on personal revelation. Spiritual path and divine intervention. Importance of surrendering ego. Learning lessons from God’s guidance. Evolving through challenges with divine direction. Embracing the right path and continuous faith practice. Sharing insight with listeners and feeling spiritual guidance. New opportunities and business alignment through faith. Time management and family priorities. Emphasizing quarterly client meetings. Encouragement to make impactful changes with faith. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Stop Putting Off Living Your Life!
08/11/2025
Stop Putting Off Living Your Life!
This episode summarizing what I and Gary's Gulch podcast are about was inspired by my client and friend Glenn. Inspired by Chat GPT's feedback on what Agency and Gary's Gulch are all about, I discuss in detail what agency is and how to stop denying yourself today to save out of fear of retirement. I'm certain God thinks you can do both, and it is my life's mission to be the guide that helps you achieve a life of prosperity both today and in retirement. Highlights Strategy for minimizing taxes. Balance between present living and future savings. Animal instincts and financial strategy. Learning and living guided by Gandhi's wisdom. Importance of financial control and agency. How agency impacts financial opportunities. Building financial agency through whole life insurance. Concepts of wealth tiers for financial stability. Tax strategies beneficial to the private economy. Advantages of revocable and irrevocable trusts. Caution against financial strategies that limit present living. The importance of financial knowledge and agency. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Finding Your Purpose is the Key to Everything
07/29/2025
Finding Your Purpose is the Key to Everything
It has been said that "The Day You Were Born, a Problem Was Solved". That's the purpose of your life, to solve that unique problem with the specific talents you were given by God to use. How do you find it? Why is it so important? Listen in and find out. Highlights Birth as a solution: Embracing purpose. Elon Musk’s mission and societal advancement. Donald Trump’s journey and divine purpose. Finding purpose through divine guidance. Insight from Henry Ford’s legacy and balance. Donald Trump: A perspective on leadership and peace. Grateful mentality and fulfillment of purpose. Questioning unique purpose: Mike Lindell’s story. The role of business in achieving divine goals. God’s intention and purposeful living. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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A Nation that Prays will Prosper
07/22/2025
A Nation that Prays will Prosper
This is the final part of our reflection on America as a Nation founded in Christianity and why it matters. President Trump famously and very recently stated in a speech "A Nation that Prays is a Nation that Prospers". I explain and tie that statement to Part 1 where Charlie Kirk expertly described the importance of our Declaration of Independence. Come listen in and learn why believing in God is essential for the continued survival of a civilized and successful human race. Highlights Existence of God Justified Trump: Nation That Prays Prospers Charlie Kirk and Chesterton’s Quote Worshipping Government and Materialism Thought Experiment on Morality Natural Law and Higher Power Covenant vs. Contractual Relationships Mafia and Business Ethics Charity Facade vs. True Evangelism Outward Focused Living and Success Conservative vs. Liberal Interpretation Morality and Abortion Debate Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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God in the USA, Part 1 - Celebrating America's Declaration and Upcoming 250th Birthday
07/18/2025
God in the USA, Part 1 - Celebrating America's Declaration and Upcoming 250th Birthday
This is the first of a two part series on understanding WHY America has been successful for 2 1/2 centuries and why it will for centuries to come - God is using the USA as his tool to attract and protect his children. Big statement? Yes, but it is true and accurate. This first part is a rebroadcast of Charlie Kirk's recent speech on the importance of our Declaration of Independence and my comments to highlight his key points. Highlights Significance of the Declaration of Independence Importance of Consistency in Podcasting Value of Ideal Subscribers Shift to Tuesday Podcast Posting Challenges Faced by Founding Fathers Debating and Drafting the Declaration Hardships of Declaration Signers Role of Faith in Declaration Signing Prioritizing Life in Declaration Contractual vs. Covenantal Relationships America’s Unique Foundational Covenant America’s Christian Influence on Founding God as a Third Party in Relationships Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Stop Repelling the VIPs in your life! Words and tonality matter
07/03/2025
Stop Repelling the VIPs in your life! Words and tonality matter
It has been said that you never get a second chance to make a first impression. Whether it is with your potential client, a new boss or your future mate, words and tonality carry a lot of weight and the ones you are using may be torpedoing your chances. Are you presenting yourself using words and a timid tone that are both full of toxic baggage? Listen in and let's find out. Highlights Questioning speech impacting opportunities. The future relationship with AI. Generational gap in job interviews. Confidence through vocal inflection. Authoritative communication vs. questioning. Humanity’s ability to adapt and overcome. Women’s intuition and decision-making. Critical thinking and the role of AI. Words and their evolving meanings. “Transitioning” and its modern implications. Avoiding language pitfalls in communication. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Can Passive Investing be done safely with Whitney Elkins-Hutten
06/27/2025
Can Passive Investing be done safely with Whitney Elkins-Hutten
Many alternative investors see passive investing in syndications as the Easy Button for mailbox money. There are many pitfalls in all kinds of investments including syndications and the only way to reduce that is through education and personal involvement in due diligence. That's why I introduce you in this podcast to one of the best investor educators in the industry. Enjoy this interview with Whitney Elkins-Hutten. Highlights Historical outsourcing of financial management. The importance of self-education in finance. The risk of abdicating financial responsibility. Pitfalls of rolling investments without due diligence. Dangers of investment honeymoon phase. Complexity and risks in syndication layers. Importance of direct investment over funds. Safe level entry for new accredited investors. Introduction to Whitney Elkins-Hutton’s expertise. Strategic use of promissory notes in real estate. Advice for navigating passive investment challenges. Current market strategy: Debt investments over equity. Links and Resources from this Episode Connect with Gary Pinkerton Connect with Whitney Elkins-Hutten Direct Mobile/Text: +1-970-988-9076 Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Advice from my Dad - Happy Father's Day!
06/20/2025
Advice from my Dad - Happy Father's Day!
Happy Father's Day to all the dads out there! I reflect on stories and wise sayings my father shared and lived out when I was a kid. Like your dad, he taught me timeless lessons that four decades later still fuels my passion for greatness - listen in to see how compassion, wisdom, kindness and street smarts from dad can lead to Agency, Freedom and preserving the American dream for your family. Highlights Inspirational wisdom from Uncle John. Father as best friend and mentor. Building a leaf book with Dad. Grace and learning from mistakes. Hardship, judgment, and experience. Cautionary banking advice. Lessons from livestock encounters. Social media and avoiding confrontations. Bumblebee and tractor misadventure. Profound life lessons from Father. Acts of kindness despite financial struggles. Legacy of wisdom and personal growth. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Reduce Taxes without the High Risk
06/13/2025
Reduce Taxes without the High Risk
In this episode, I discuss the tools available in 2025 and for the next few years that allow business owners and high-earning W2 earners to eliminate the very destructive higher tax brackets without taking risk that you lose all the investment. Saving your hard-earned money from taxes is a powerful emotion and enables the "tax tail to wag the dog" - we get into investments we would not have made with people we don't know because of this emotion. Listen in to hear how reducing taxes is achievable with lower risk strategies in Hierarchy of Wealth Tier 2 - things you directly control. Highlights Personal connection to taxes pain. Parable of earning money value. Lessons from failed investments. Questioning ethical tax reduction. Real estate depreciation strategy. Hierarchy of wealth explanation. Section 179 and business benefits. Captive insurance as a strategy. Comfort with paying reasonable taxes. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Trump Tariffs: The American Wealth Engine!
06/06/2025
Trump Tariffs: The American Wealth Engine!
Those in our government and corporate media would have you believe Tariffs are an act of war and recipe to destroy the American economy and way of life. They pretend that tariffs were not used before or that they were not what fueled our country for 150 years before we created income taxes. They're intentionally leading you astray. Under President Trump's approach we've already seen success with the best economy in the month of May in the last 30 years. Trillions of dollars of foreign country investment in the US. You can use the same principals and tools in your own personal economy - listen in to find out how. Highlights Donald Trump and tax discussion. American ingenuity and freedom. Tariffs as a strategic tool. Economic achievements under Trump. Historical use of tariffs. Shift from self-reliance to dependency. Shift to income tax in the 20th century. Post-war economic leverage and its cost. Addressing trade imbalances. Influences on U.S. industrial base. Calls for policy reevaluation. Paradigm Life’s wealth strategy pillars. Importance of cash flow management. Role and use of life insurance. Strategic asset organization. Personal and national wealth creation strategies. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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MAGA Economic Strategy - Leadership Trumps Basic Math
05/30/2025
MAGA Economic Strategy - Leadership Trumps Basic Math
ent actions and their impact on the economy. Individuals look at the reconciliation act called the One Big Beautiful Bill act (OBBB) and that it cuts potentially $4.5T in revenue over the next 5 years and they determine that means our debt will go up by that amount. President Trump is using leadership tools to move our economy in the opposite direction. Specifically he's spurring significantly greater production domestically while simultaneously bringing in revenue from outside the country, specifically massive investment and tariffs. Tariffs are how we funded our country to be #1 in the world for its first 100 years and it will work again. He brought in $10T of investment commitments in one foreign trip this month. Give Trump some time to show the benefits of 'The Art of the Deal' and you will see the USA flourish as it did in the 19th century. MAGA! Highlights Tariff fears and economic impact. Legislative hurdles for tax reform. Leadership’s role in economic growth. Middle East investment in the US. The power of reducing external taxes. House vs. Senate tax bill dynamics. The importance of maintaining business confidence. Home office and self-employment tax benefits. Transitioning to self-employment for tax advantages. Real estate investment tax strategies. Bonus depreciation and Section 179 benefits. Impact of cost segregation on tax deductions. Beware of tax-driven investment pitfalls. Rescission and future economic plans. Leadership’s potential to drive national recovery. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Culture Drives your Team's Success
05/23/2025
Culture Drives your Team's Success
If you run a team, a company or another organization, Culture above all else Drives your Success. And you have to Truly KNOW your people to build and sustain a winning culture. Highlights Empower your subordinates (employees; teammates) so they take the action you’d take, not ask ‘what should I do?’ Breed Readiness and Competency; the process I used and share here is: Study – Discuss – Role Play – Simulate – Perform – Learn from it Checking the organization's Temperature often; have TWO independent ways to know what your people are thinking and what’s going on. Build a Clear, Unbreakable Culture so your team clearly knows what the company and you stand for and every action supports this culture especially when you’re not around. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Baby Boomers in a Trance, a Risk to Freedom in the USA
05/16/2025
Baby Boomers in a Trance, a Risk to Freedom in the USA
Baby Boomers will retain the largest voting block through the 2026 midterms and while they are moving conservative, it is not happening quickly enough because of the hold that legacy media continues to hold on this cohort. I need agency-minded followers out there to adopt a boomer, have conversations with them, take them to lunch, expose them to what alternative media has been reporting for 5+ years - President Trump is creating huge wins every day but that message is not getting to the Baby Boomers via CNN or even Fox. Pitch in, get vocal with these seniors and let's MAGA! Highlights Retirement and scarcity mindset. Value of not retiring too early. Conservative shift among younger generations. Gen X’ role and conservatism. Global political influence and actions. Impact of international tariffs. National media’s impact on baby boomers. Generational conservatism and politics. Importance of engaging baby boomers politically. Trump’s global vision for freedom. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review by Make sure you’re subscribed to the podcast so you get the latest episodes. Subscribe with Follow on Subscribe with Subscribe with
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Want to Continuously Improve? Keep Score!
05/09/2025
Want to Continuously Improve? Keep Score!
Good teams get it right about half the time. Great teams work hard, build skill, and get it right most of the time. Exceptional teams excel because they critically review even their best performances to see what wasn't perfect that they could learn from and do better on the next time. It is a process that some call Plan-Do-Review and it was essential to high performance in the nuclear submarine force and for every team I've been on since. Highlights Networking with clients in person. Aspire for More Mastermind Group. Introduction to captive insurance. Switch to exclusively using Delta Airlines. The role of faith in aligning life choices. Concept of continuous improvement. U.S. Navy Nuclear Submarine Force’s approach. High stakes in executive officer training. Importance of critical evaluation. Submarine valve error illustration. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review Make sure you’re subscribed to the podcast so you get the latest episodes.
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Busting Financial Myths
05/02/2025
Busting Financial Myths
In this episode I tackle some common 'partial truths' that I hear from financial pundits and as concerns from clients who have encountered them and been sucked into their surface level statement. Context is huge, and understanding if these financial myths have any truth or apply at all to your situation is key to long term success. Please provide feedback if this episode was valuable or if you disagree - Highlights Lies vs. myths in finance. Misleading financial taglines. Whole life insurance expense debate. Liquidity during crises. Universal life insurance misconceptions. Sequence of return risks. Cash flow vs. net worth dilemma. Importance of collaborating in financial decisions. Return on investment vs. return on wealth. Links and Resources from this Episode Connect with Gary Pinkerton Review, Subscribe and Share If you like what you hear please leave a review Make sure you’re subscribed to the podcast so you get the latest episodes.
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