Working Wealth Podcast

Why do intelligent, successful people still make terrible financial decisions?

Knowing more about money does not make anyone immune to fear, overconfidence, persuasive marketing, or FOMO. In fact, expertise can sometimes make it easier to justify a bad decision.

In this episode of Working Wealth, Patrick and Trevor share some of their own financial mistakes and examine the behavioral biases that cause smart people to make poor money decisions.

They discuss:

Financial success is rarely about finding one brilliant strategy. More often, it comes from maintaining strong fundamentals, recognizing your blind spots, and refusing to let emotion take control of the steering wheel.

No matter how much you earn or how financially knowledgeable you become, you never graduate from the basics.

Subscribe for candid conversations about investing, retirement planning, financial behavior, and building wealth without losing sight of what it is for.

Discussions in this show are for entertainment and educational purposes only and should not be construed as specific recommendations or investment advice. Always consult with your investment professional before making important financial decisions.

Would an extra 2% in investment returns transform your financial future?

It might help. But the decisions that have the greatest effect on your wealth often happen long before you choose a mutual fund, stock, or retirement account.

In this episode of Working Wealth, Patrick and Trevor discuss the financial and personal choices that can have a greater long-term impact than chasing higher investment returns.

They explore:

Investment performance matters, especially over long periods of time. But returns are only one piece of the equation.

Your income, savings habits, relationships, health, career, and ability to stay consistent may ultimately shape your future far more than whether one investment earns slightly more than another.

The better question is not simply, “How can I earn a higher return?”

It is, “What am I building this wealth so that I can do?”

Subscribe for practical conversations about investing, retirement planning, taxes, and using wealth to create independence and impact.

Discussions in this show are for entertainment and educational purposes only and should not be construed as specific recommendations or investment advice. Always consult with your investment professional before making important financial decisions.

Inflation is often described as one of the greatest threats to retirement. But does rising inflation affect every retiree in the same way?

In this episode of Working Wealth, Patrick and Trevor debate whether inflation is truly the biggest risk to your retirement and explain why the answer depends heavily on your spending, assets, housing costs, and overall financial plan.

They discuss:

Inflation is real, and it should be included in any responsible retirement projection. But it does not affect every household equally, and it does not automatically have to derail your financial future.

The goal is not to predict exactly what everything will cost decades from now. It is to build a plan with enough flexibility, growth, and margin to adapt as life changes.

Subscribe for more practical conversations about retirement planning, investing, taxes, and building long-term wealth.

Discussions in this show are for entertainment and educational purposes only and should not be construed as specific recommendations or investment advice. Always consult with your investment professional before making important financial decisions.

A new federal retirement savings program could give eligible Americans a 50% match on their contributions, up to $1,000. But is the so-called “Trump IRA” actually a valuable wealth-building tool, or is it simply repackaging options that already exist?

In this episode of Working Wealth, Patrick and Trevor break down the proposed Trump IRA platform and the new Federal Saver’s Match expected to replace the current Saver’s Credit beginning in 2027.

They discuss:

Every financial tool may have a place, but “free money” should never replace thoughtful planning. Before opening a new account, it is important to understand who benefits, what restrictions apply, and how it supports your larger retirement strategy.

Subscribe for practical conversations about retirement planning, investing, taxes, and building wealth with greater intention.

Discussions in this show are for entertainment and educational purposes only and should not be construed as specific recommendations or investment advice. Always consult with your investment professional before making important financial decisions.

For many investors, the S&P 500 has become the default answer.

Open social media, browse investing forums, or listen to financial influencers, and you'll hear the same message over and over:

"Just buy the S&P 500."

But is it really that simple?

In this episode of the Working Wealth Podcast, Patrick Rogers and Trevor Rasmussen break down what the S&P 500 actually is, why it's become so popular, and whether investing exclusively in the index is truly as diversified as many people believe.

They discuss concentration risk, market-cap weighting, large-cap dominance, international diversification, small-cap investing, and the tradeoffs between simplicity and portfolio construction.

The goal isn't to criticize the S&P 500. It's to help investors better understand what they own and how different pieces of a portfolio work together.

Topics Covered:

What is the S&P 500? · Market-cap weighting · Diversification explained · Large-cap stocks · International investing · Small-cap stocks · Portfolio construction · Concentration risk · Index fund investing · Long-term investing · Asset allocation

Most people spend a lot of time deciding what to invest in.

Very few spend enough time thinking about where those investments should live.

In this episode of the Working Wealth Podcast, Patrick Rogers and Trevor Rasmussen break down the three major tax buckets that make up most financial plans: pretax accounts, Roth accounts, and taxable brokerage accounts.

They explain how each bucket works, the tradeoffs of each approach, and why understanding tax treatment may be just as important as choosing the right investments.

The conversation covers traditional 401(k)s, IRAs, Roth accounts, tax-deferred growth, tax-free growth, Roth conversions, retirement income planning, inheritance considerations, and the role taxable accounts can play in creating flexibility.

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.

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.

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

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