Working Wealth Podcast

Hosted by Patrick Rogers CFP®

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Jun 2026

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About the show

Join us, Haley and Patrick Rogers, for genuine conversation on turning dreams into reality and how we help people gain clarity about developing their wealth. We will be unraveling the chapters of our personal journey in business, why we got into the wealth management industry and, why we love helping others. It's personal, raw, and relatable. But this isn't just about us—it's about you.

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46 recent

June 15, 202645 min

Term Life Beats Whole Life? Let's Talk About It

Life insurance is one of the most important financial tools available... and one of the most misunderstood. In this episode of the Working Wealth Podcast, Patrick Rogers and Trevor Rasmussen break down the major types of life insurance, including term life, whole life, universal life, indexed universal life (IUL), and variable life insurance. They discuss what life insurance is actually designed to do, why so many families are underinsured, and how different policy structures work in the real world. The conversation also explores the strengths and weaknesses of cash value policies, how life insurance pricing works, what makes someone uninsurable, and why many financial professionals recommend starting with term coverage before considering more complex strategies.

June 1, 202632 min

The Insurance Policies We Think Are a Waste of Money

Not all insurance is created equal. In Part 2 of our insurance series, Patrick Rogers and Trevor Rasmussen break down some of the most common insurance products consumers are sold and explain why many of them may not make sense for the average person. From credit life insurance and mortgage protection policies to supplemental coverages, the insurance marketplace is filled with products that sound helpful on the surface but may not provide the value many people expect. The goal of this episode isn't to tell you what to buy. It's to help you think critically about risk, coverage, and whether a policy actually solves a problem in your financial life. If you've ever wondered whether you're paying for insurance you don't really need, this episode will help you separate useful protection from expensive add-ons.

May 25, 202643 min

Most People Are Using Insurance Completely Wrong

Most people think about insurance backwards. In this episode of the Working World Podcast, Patrick Rogers and Trevor break down what insurance is actually designed to do, how it fits into a financial plan, and why so many people either overbuy the wrong coverage… or completely ignore the risks that matter most. From health insurance and disability coverage to homeowners, auto, umbrella, and long-term care policies, this episode explores how insurance functions as financial defense — not wealth building. They also discuss why medical debt remains one of the biggest financial risks in America, how liability coverage protects accumulated assets, and why many insurance products are marketed in ways that confuse consumers. If you’ve ever wondered: “What insurance do I actually need?” “How much coverage is enough?” “Is insurance an investment?” “What financial risks should I actually worry about?” …this episode is for you. Topics covered: What insurance is actually for · Insurance vs investing · Medical debt and financial risk · Disability insurance · Auto and homeowners coverage · Umbrella policies · Liability protection · Long-term care planning · Asset protection · Underinsurance risks · How insurance fits into a financial plan 00:00 – Intro & Podcast Disclaimer 00:37 – Why Insurance Confuses So Many People 01:15 – What Insurance Is ACTUALLY For 02:05 – Offense vs Defense in Financial Planning 03:20 – Why Protection Matters Before Growth 05:00 – Medical Debt & Financial Risk 07:15 – The Most Important Types of Insurance 09:30 – Disability Insurance Explained 12:00 – Health Insurance & Catastrophic Events 14:20 – Traditional vs Nontraditional Health Coverage 16:45 – Health Sharing Ministries & Alternatives 18:30 – What “Proper Coverage” Actually Means 20:00 – Auto Insurance Explained 22:10 – Liability Coverage & Lawsuits 24:45 – Why Umbrella Policies Matter 27:15 – Protecting Assets as Wealth Grows 29:40 – Cybersecurity & Identity Theft Risks 32:10 – Long-Term Care Insurance Basics 34:50 – Estate Planning & Insurance 36:40 – The Biggest Insurance Mistakes People Make 39:15 – Final Thoughts & Risk Management Philosophy

May 11, 202650 min

Most People Have No Idea How Their Health Insurance Works

Most people don't think about health insurance until they're forced to — and by then, it gets expensive fast. Patrick Rogers and Josh Crumley of HealthMarkets break down ACA marketplace plans, private coverage, Medicare, and the 2026 subsidy cliff. If you're self-employed, retiring before 65, or losing employer coverage, the rules just changed — and this episode explains what that means for your financial plan. Topics covered: ACA marketplace vs. private insurance · Health insurance before Medicare at 65 · The 2026 ACA subsidy cliff · Medicare planning basics · Deductibles and out-of-pocket costs · Healthcare costs in retirement · Health sharing ministries · COBRA and coverage gaps · Common insurance mistakes · How health insurance affects your overall financial plan. 00:00 – Intro & Podcast Disclaimer 00:38 – Meet Josh Crumley & Why Health Insurance Matters 01:28 – Why Health Insurance Feels So Complicated Today 02:45 – The Different “Buckets” of Insurance Plans 05:00 – Why Premiums Have Changed So Much 07:58 – ACA Plans vs Private Insurance 10:45 – Health Sharing Ministries & Alternative Options 13:40 – What People Need to Know About Coverage Limits 16:25 – Provider Networks Explained 19:15 – Understanding Deductibles, Copays & Out-of-Pocket Costs 22:05 – What Happens If You Don’t Have Coverage 24:50 – Emergency Care, Hospitals & Financial Risk 27:25 – Why Healthy People Still Need a Strategy 30:10 – Healthcare Costs & Retirement Planning 32:55 – Medicare Basics & Planning Ahead 35:30 – How the Industry Has Changed Over the Years 38:15 – The Biggest Mistakes People Make With Insurance 40:40 – Planning for Future Healthcare Expenses 43:40 – Long-Term Care & Aging Considerations 46:30 – Final Thoughts on Flexibility & Financial Planning 49:00 – Where to Learn More & Closing Thoughts

April 6, 202647 min

Why High Earners Still Feel Broke | Income, Lifestyle Creep & Creating Financial Margin

Many people believe making more money will solve their financial problems. But in reality, higher income often hides financial issues instead of fixing them. In this episode of The Working Wealth Podcast, Patrick Rogers and Trevor Rasmussen discuss why so many people earning strong incomes still feel financially stuck. They break down how lifestyle creep happens, why money can feel “spoken for” before it ever reaches your account, and how creating financial margin can dramatically change your financial future. The conversation also covers simple systems that help people regain control of their finances — including micro-goals, better cash-flow awareness, and structuring accounts intentionally. If you feel like you should be further ahead financially despite earning good money, this episode will help explain why — and what to do about it. To connect with Patrick, visit planwithpatrick.com or follow us on Instagram at @smartprogvl

March 23, 202654 min

Jonathan Godwin | Tax Season Is Here: Avoid These Costly Filing Mistakes (Small Business, W-4s & Overtime Changes)

Tax season is here — and most people are reacting instead of planning. In this episode, Patrick sits down with CPA Jonathan Godwin to break down what proactive tax planning actually looks like for small business owners and everyday W-2 earners. If you're filing taxes right now, this conversation may save you thousands. They cover: • Why tax planning should happen year-round — not just during tax season • How small business owners avoid surprise $40,000 tax bills • Why tax refunds are NOT “bonuses” — they’re math • The hidden danger of ignoring your W-4 and paycheck withholding • How being close to the next tax bracket creates planning opportunities • The truth about the new overtime deduction • Why “no tax on Social Security” was misunderstood • How upcoming sunset tax laws could change everything Most people only think about taxes for a few weeks every year. The people who build wealth plan for them all year long. If you're a business owner, overtime earner, retiree, or someone who simply wants fewer surprises this tax season — this conversation is for you. To connect with Patrick, visit planwithpatrick.com or follow on Instagram at @smartprogvl

March 9, 202632 min

Self-Employed? Here’s How You Actually Build Wealth | Working Wealth Podcast

Why do so many high-income people still feel broke? In this episode of the Working Wealth Podcast, Patrick Rogers and Trevor Rasmussen dive into a common problem they see in real client conversations — people making good money but still struggling to build real wealth. A major part of the conversation focuses on investment opportunities and financial systems for self-employed individuals and business owners. When your income doesn’t come from a traditional paycheck, saving and investing requires a more intentional strategy. Patrick and Trevor break down how entrepreneurs can create structure around their money so that taxes, investing, and long-term wealth building happen automatically. They also discuss why many self-employed people fall into the trap of spending what they earn instead of building systems that consistently move money toward the future. In this episode, they cover: • Why high income doesn’t automatically lead to wealth • The biggest financial mistake many self-employed professionals make • How business owners can create systems for taxes, investing, and savings • Why separating accounts and building intentional money flows matters • How to think about investing when your income is variable • The mindset shift required to move from earning money to building wealth If you're self-employed, a small business owner, or someone with irregular income, this conversation will help you think differently about how to structure your finances and take advantage of the opportunities available to you.

February 23, 20261 hr 4 min

Time in the Market Beats Timing the Market | Working Wealth Podcast

Trying to wait for the perfect moment to invest is one of the most expensive mistakes people make. In this episode, Patrick Rogers and Trevor Rasmussen break down why time in the market consistently beats timing the market, how real wealth is built through owning productive businesses, and why diversification matters more than ever in today’s market. We also cover the dangers of get-rich-quick investing, the concentration risk of the “Magnificent Seven,” how inflation quietly erodes cash, and the simple framework that actually works: create margin, invest consistently, and let time do the heavy lifting. To connect with Patrick, visit planwithpatrick.com or follow on Instagram at @smartprogvl.

February 9, 202649 min

How to Invest for Your Child’s Future (529s, Roth IRAs & Smart Family Wealth) | Working Wealth Podcast

Saving for education sounds simple — until taxes, account types, and rules get involved. In this episode, we break down how education savings really work, including 529 plans, taxable accounts, and the tax treatment behind each option. We explain what’s actually tax-free, what’s tax-deferred, and where people commonly get confused. If you’re saving for a child’s education — or planning to — this episode will give you clarity and help you avoid costly mistakes. To connect with Patrick, visit planwithpatrick.com or follow on Instagram at @smartprogvl.

January 26, 202646 min

South Carolina Retirement System Explained | SCRS, PORS, DCP Breakdown

If you work for the state of South Carolina, are a teacher, law enforcement officer, or public employee — you need to understand how your retirement benefits actually work. In this episode of The Working Wealth Podcast, we break down the South Carolina Retirement System (SCRS), the Police Officers Retirement System (PORS), vesting rules, pension calculations, and the Deferred Retirement Option Program (DROP). We discuss: • How SCRS and PORS calculate your pension • When you become vested • How service credit impacts your benefit • How DROP works • Survivor benefit considerations • Whether rolling funds into an IRA ever makes sense • Why your pension should not be your only retirement strategy Your pension is powerful — but it’s just one piece of your overall retirement income plan. If you’re planning to retire in South Carolina, this episode will help you avoid costly mistakes and make more confident decisions. To connect with Patrick, visit planwithpatrick.com or follow on Instagram at @smartprogvl.