Working Wealth Podcast

Patrick Rogers CFP®
  • 5.0 (9)
  • MANAGEMENT

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.

  1. 4D AGO

    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

    51 min

  2. APR 6

    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

    48 min

  3. MAR 23

    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

    55 min

  4. MAR 9

    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.

    32 min

  5. FEB 23

    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.

    1h 4m

  6. FEB 9

    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.

    50 min

  7. JAN 26

    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.

    47 min

  8. JAN 5

    How Katie Built a Thriving Business From Zero: Clarity, Courage, and the Hard Conversations

    In this episode, Patrick sits down with Katie Riegel for a raw, practical look at what it really takes to build a business that lasts. From navigating impostor syndrome to raising her prices, setting better boundaries, hiring help, and learning to trust her instincts, Katie opens up about the exact steps and the uncomfortable conversations that helped her go from uncertain to unstoppable. You’ll hear Patrick dig into the turning points, mindset shifts, and strategy changes that shaped Katie’s growth, plus the simple habits that helped her build a business that serves her clients and her life. If you’re a business owner trying to scale, simplify, or find clarity again, this conversation hits home.

    1 hr
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Ratings & Reviews

5
out of 5
9 Ratings

About

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.

Information

  • Creator
    Patrick Rogers CFP®
  • Years Active
    2024 - 2026
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © 2023 Working Wealth Podcast
  • Show Website
    Working Wealth Podcast