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Retire With Confidence
Josh Duncan, CFP®
18 episodes
5 days ago
Retire With Confidence is the podcast designed to help you move beyond the fear of the complexity of finances so you can be financially free to achieve personal significance. Tune in with Josh Duncan each week to turn fear into fuel that drives you into Freedom & Significance.
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All content for Retire With Confidence is the property of Josh Duncan, CFP® and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Retire With Confidence is the podcast designed to help you move beyond the fear of the complexity of finances so you can be financially free to achieve personal significance. Tune in with Josh Duncan each week to turn fear into fuel that drives you into Freedom & Significance.
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Investing
Business
Episodes (18/18)
Retire With Confidence
How a Taxable Brokerage Account Fits Into Your Retirement Plan

If you already have a 401(k), a Roth IRA, and maybe even a Health Savings Account, you might be asking a logical next question: Where does the next dollar go?

In this video, Josh breaks down the often-overlooked role of a taxable brokerage account in a well-designed retirement plan and why, for many high-income families, it becomes one of the most powerful and flexible tools available.


Taxable brokerage accounts are frequently misunderstood. They are not just “extra” accounts or short-term investing vehicles. When used intentionally, they can support early retirement, improve tax efficiency, smooth income over decades, and provide flexibility that traditional retirement accounts simply cannot.

We walk through how taxable brokerage accounts complement tax-deferred and tax-free accounts, why “taxable” does not automatically mean “tax inefficient”, and how long-term capital gains, tax-loss harvesting, and thoughtful asset placement can dramatically change your retirement.

Most importantly, this conversation focuses on retirement planning at the household level—not account by account—so your strategy works across multiple decades, tax environments, and market cycles.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com.


About F5 Financial Planning:


At F5 Financial Planning, we help individuals and families align their finances with what matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.


At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most. 


Visit https://www.f5fp.com to learn more about our services and planning process.


*****


Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered investment adviser. This content is for educational and informational purposes only and should not be considered personalized financial, investment, tax, or legal advice.


Viewing these videos does not create an advisory relationship with F5 Financial. All investments involve risk, including possible loss of principal. For guidance specific to your situation, please consult a qualified professional.

Show more...
5 days ago
11 minutes

Retire With Confidence
How to Maximize Retirement Contributions While Maintaining Cash Flow

Are you confident you’re truly maximizing your retirement account contributions or could small decisions today be limiting your flexibility tomorrow?

Many high-earning families contribute consistently to their retirement accounts, yet still miss opportunities to improve tax efficiency, increase long-term flexibility, and better align contributions with their broader financial plan. In this episode, Josh breaks down how to maximize retirement contributions in a way that is intentional, sustainable, and tax-aware.

You’ll learn how to prioritize retirement accounts strategically, why contribution limits alone should not dictate your strategy, how tax diversification plays a critical role in retirement income planning, and why higher-income households must move beyond one-size-fits-all advice.

Josh also covers commonly overlooked opportunities and the real limiting factor most families face: cash flow. Maximizing contributions is not about perfection—it’s about making informed decisions that compound over time.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com


About F5 Financial Planning:


At F5 Financial Planning, we help individuals and families align their finances with what matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.


At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most. 


Visit https://www.f5fp.com to learn more about our services and planning process.


*****


Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered investment adviser. This content is for educational and informational purposes only and should not be considered personalized financial, investment, tax, or legal advice.


Viewing these videos does not create an advisory relationship with F5 Financial. All investments involve risk, including possible loss of principal. For guidance specific to your situation, please consult a qualified professional.

Show more...
1 week ago
12 minutes

Retire With Confidence
How to Add Charitable Giving to Your Financial Plan

In this episode, Josh breaks down how to incorporate charitable giving into a comprehensive financial plan that is intentional, sustainable, and tax-efficient. If you’ve ever wondered how much you can afford to give, how to align generosity with long-term goals, or how to support the causes you care about without jeopardizing financial security, this conversation is built for you.


You will learn why charitable giving belongs in a well-structured financial plan, how to build a personal giving strategy that reflects your values, and which advanced techniques can help high-net-worth families give more while optimizing tax outcomes. 

Josh covers key strategies such as donating appreciated assets, using donor-advised funds, leveraging qualified charitable distributions, and applying charitable bunching to maximize deductions. You will also see how giving fits into retirement planning, estate planning, and legacy conversations with your family.


Whether you’re focused on impact, tax efficiency, or long-term stewardship, you will walk away with a clear framework for giving generously and wisely.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com


About F5 Financial Planning:


At F5 Financial Planning, we help individuals and families align their finances with what matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.


At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most. 


Visit https://www.f5fp.com to learn more about our services and planning process.


*****


Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered investment adviser. This content is for educational and informational purposes only and should not be considered personalized financial, investment, tax, or legal advice.


Viewing these videos does not create an advisory relationship with F5 Financial. All investments involve risk, including possible loss of principal. For guidance specific to your situation, please consult a qualified professional.

Show more...
2 weeks ago
14 minutes

Retire With Confidence
Top 5 Retirement Planning Pitfalls You Can Avoid

Planning for retirement is one of the most important financial decisions you will ever make, yet even smart, disciplined families fall into avoidable traps. In this video, we break down the top five retirement planning pitfalls that derail long-term financial independence and peace of mind.


You’ll learn why guessing at your “retirement number” leads to overspending, how retiring too early without a distribution plan can drain your portfolio, why longevity risk magnifies every other financial risk you face. 


We also unpack the tax mistakes many households overlook—especially when managing withdrawals across taxable, tax-deferred, and Roth accounts. And finally, we address one of the most underestimated issues: entering retirement without a clear sense of purpose.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com


About F5 Financial Planning:


At F5 Financial Planning, we help individuals and families align their finances with what matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.


At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most. 


Visit https://www.f5fp.com to learn more about our services and planning process.


*****


Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered investment adviser. This content is for educational and informational purposes only and should not be considered personalized financial, investment, tax, or legal advice.


Viewing these videos does not create an advisory relationship with F5 Financial. All investments involve risk, including possible loss of principal. For guidance specific to your situation, please consult a qualified professional.

Show more...
3 weeks ago
12 minutes

Retire With Confidence
How to Build a Diversified Investment Portfolio (Without Owning 20+ Funds)

A diversified investment portfolio isn’t about owning as many funds as possible—it’s about owning the right asset classes in the right proportions. In this video, Josh Duncan breaks down how families with significant wealth can build a truly diversified investment portfolio that supports long-term goals, reduces unnecessary volatility, and avoids the clutter that derails even the smartest investors.


Using a simple framework built around five or six core asset classes—US large cap equities, US small cap equities, developed international stocks, emerging markets, real estate, and bonds—Josh explains why simplicity often beats complexity. 

You’ll learn how to avoid overlapping investments, how to structure your portfolio at the household level rather than account by account, and how tax-efficient placement of assets can meaningfully improve long-term results.


Whether you're evaluating your current strategy or starting fresh, this video breaks down the purpose of each asset class, the role it plays in risk management, and how to build a unified, well-balanced portfolio across all accounts.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com


About F5 Financial Planning:


At F5 Financial Planning, we help individuals and families align their finances with what matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.


At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most. 


Visit https://www.f5fp.com to learn more about our services and planning process.


*****


Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered investment adviser. This content is for educational and informational purposes only and should not be considered personalized financial, investment, tax, or legal advice.


Viewing these videos does not create an advisory relationship with F5 Financial. All investments involve risk, including possible loss of principal. For guidance specific to your situation, please consult a qualified professional.

Show more...
1 month ago
15 minutes

Retire With Confidence
Pay Off Your Mortgage Early Using a Side Fund—Not Extra Principal Payments

Paying off your mortgage early is one of the most common financial goals, but most people
never learn the smarter, safer alternative to sending extra principal payments to the lender. In
this video, Josh breaks down a powerful strategy called the side fund mortgage payoff
method, which protects your liquidity while still helping you eliminate your mortgage years
ahead of schedule.

You’ll learn why traditional extra mortgage payments lock away your money, how a side fund
keeps you flexible, and why this approach often produces better long-term outcomes—
especially for families with meaningful assets and complex financial priorities.
We’ll walk through the pros and cons of a money-market side fund vs. a brokerage side fund,
how to manage volatility, and the step-by-step process to determine your payoff timeline. If
you want the confidence of maintaining your cash flow and the freedom of a mortgage-free
life, this video will show you exactly how to do it.

Want to achieve financial freedom for personal significance? Work with us at https://
www.f5fp.com

About F5 Financial Planning:

At F5 Financial Planning, we help individuals and families align their finances with what
matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary
financial planning and investment management firm, meaning we don’t earn commissions or
sell products — our only commitment is to our clients’ best interests. We provide
comprehensive financial planning, investment management, tax-efficient strategies, and
retirement planning for families, corporate executives, and entrepreneurs. Our team serves
clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida.

At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial
future so you can focus on the people and passions that matter most.

Visit https://www.f5fp.com to learn more about our services and planning process.

*****

Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered
investment adviser. This content is for educational and informational purposes only and
should not be considered personalized financial, investment, tax, or legal advice.

Viewing these videos does not create an advisory relationship with F5 Financial. All
investments involve risk, including possible loss of principal. For guidance specific to your
situation, please consult a qualified professional.

Show more...
1 month ago
19 minutes

Retire With Confidence
How to Create Your One-Page Financial Plan

Financial freedom is just one page away!
DOWNLOAD → https://www.f5fp.com/wp-content/uploads/2025/11/F5-Financial-One-Page-Financial-Plan-Template.pdf

If you’re feeling overwhelmed by your finances, you’re in the right place. This video teaches you how to unlock the power of clarity with a simple yet powerful tool—your one-page financial plan. No complex spreadsheets or jargon—just straightforward steps to help you stay focused and make confident decisions every day.

We'll explore why a one-page plan works better than lengthy documents that get ignored, and how it can serve as your personal dashboard that keeps you aligned with what truly matters. Whether you're looking to pay off the mortgage early, build a legacy, or achieve financial independence, this approach puts control back in your hands.

Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com

About F5 Financial Planning:

At F5 Financial Planning, we help individuals and families align their finances with what
matters most so they can live lives of Freedom and Significance. We are a fee-only, fiduciary financial planning and investment management firm, meaning we don’t earn commissions or sell products — our only commitment is to our clients’ best interests. We provide comprehensive financial planning, investment management, tax-efficient strategies, and retirement planning for families, corporate executives, and entrepreneurs. Our team serves clients nationwide through virtual meetings and from offices in Illinois, Georgia and Florida. 

At F5, our goal is simple: to help you gain confidence, clarity, and control over your financial future so you can focus on the people and passions that matter most.

Visit https://www.f5fp.com to learn more about our services and planning process.

*****

Advisory services are offered through F5 Financial Planning, LLC, an SEC-registered
investment adviser. This content is for educational and informational purposes only and
should not be considered personalized financial, investment, tax, or legal advice.

Viewing these videos does not create an advisory relationship with F5 Financial. All
investments involve risk, including possible loss of principal. For guidance specific to your
situation, please consult a qualified professional.

Show more...
1 month ago
18 minutes

Retire With Confidence
Your Roadmap to Financial Freedom in 5 Steps

Many people save, invest, and pay off debt, but still wonder: Am I actually on the right track?
In this video, financial advisor Josh Duncan walks you through a clear, 5-step process to build
your personal financial roadmap—a plan that turns your values into meaningful progress
toward financial freedom and personal significance. By the end, you’ll know how to make your
money work for you, not the other way around.

Want to achieve financial freedom for personal significance? Work with us at https://
www.f5fp.com.

At F5 Financial Planning, we help individuals and families align their finances with
what matters most so they can live lives of Freedom and Significance.

We are a fee-only, fiduciary financial planning and investment management firm,
meaning we don’t earn commissions or sell products — our only commitment is to
our clients’ best interests.

We provide comprehensive financial planning, investment management, tax-efficient
strategies, and retirement planning for families, corporate executives, and
entrepreneurs.

Our team serves clients nationwide through virtual meetings and from offices in
Illinois, Georgia and Florida.

At F5, our goal is simple: to help you gain confidence, clarity, and control over your
financial future so you can focus on the people and passions that matter most. 

Visit https://www.f5fp.com to learn more about our services and planning process.

*****

Advisory services are offered through F5 Financial Planning, LLC, an SEC-
registered investment adviser. This content is for educational and informational
purposes only and should not be considered personalized financial, investment, tax,
or legal advice.

Viewing these videos does not create an advisory relationship with F5 Financial.

All investments involve risk, including possible loss of principal.

For guidance specific to your situation, please consult a qualified professional.

Show more...
1 month ago
14 minutes

Retire With Confidence
Traditional Insurance vs Health Sharing: What to Know Before You Switch

Have rising health insurance premiums left you wondering if there’s a better way? In this episode, financial advisor Josh Duncan takes you through a comprehensive, firsthand analysis of health sharing programs and how they compare to traditional insurance.


After seven years of using health sharing for his own family of five, Josh reveals what’s worked, what hasn’t, and the key lessons families should know before making the switch.


Want to achieve financial freedom for personal significance? Work with us at https://www.f5fp.com.

Show more...
2 months ago
17 minutes

Retire With Confidence
How to Align Your Spending with What Truly Matters

Ever feel like you’re doing everything “right” with money but still not satisfied? In this video, we uncover why your spending might not align with your values—and how to fix it. You’ll learn how to identify what truly matters to you, evaluate where your money actually goes, and design a spending plan that supports a more meaningful life.

Financial freedom isn’t just about saving—it’s about making sure your money reflects your priorities. Watch until the end for simple steps to create a values-based spending plan that finally feels right.

Work with us → https://www.f5fp.com/

Show more...
2 months ago
13 minutes

Retire With Confidence
How to Budget Your Household Expenses Like a Pro (Save Hundreds Every Month)

Managing your household expenses efficiently is one of the most powerful ways to build financial stability and peace of mind. In this video, we’ll walk through practical strategies to take control of your spending, organize your budget, and make your money work for you. From tracking expenses and cutting waste to automating savings and setting clear priorities, you’ll learn how to create a plan that fits your lifestyle.

Whether you’re managing a family budget, preparing for retirement, or just looking to save more each month, these simple and effective tips will help you gain confidence and control over your finances.

Work with us → https://www.f5fp.com/

Show more...
2 months ago
23 minutes

Retire With Confidence
How Busy People Can Crush Debt Fast

Drowning in debt but too busy to figure it out? You’re not alone. Many professionals struggle to balance demanding careers with smart money management. In this short, we share simple, practical debt reduction strategies designed for busy professionals who want to save time and money.

From automating payments and prioritizing high-interest debt to using proven financial frameworks, these strategies can help you reduce stress, take control of your finances, and work toward financial freedom—even with a hectic schedule.

Work with us → https://www.f5fp.com/

Show more...
2 months ago
9 minutes

Retire With Confidence
The Secret Behind Big Executive Paychecks

When it comes to executive compensation, the salary is only part of the picture. In this video, we’ll break down the executive benefits and perks that often go overlooked—but can add significant value to your financial plan. From stock options and deferred compensation to retirement packages, insurance benefits, and unique perks, you’ll discover how executives can maximize what’s available to them.

If you’re in an executive role—or on the path to becoming one—understanding your full benefits package is critical. Watch until the end to learn how to align these perks with your long-term financial goals and retirement strategy.

Work with us → https://www.f5fp.com/

Show more...
2 months ago
12 minutes

Retire With Confidence
How To Make More Money Without Quitting Your Job

Relying on a single paycheck can be risky—so how do you build multiple income streams from your career? In this video, we’ll explore practical ways to diversify your earnings without starting from scratch. From side hustles and consulting to passive income and skill stacking, you’ll learn how to create long-term financial security by leveraging the career you already have.

Whether you’re planning for financial independence, early retirement, or simply want to reduce stress around money, building multiple income streams is one of the smartest moves you can make. Watch until the end for strategies you can start applying today.

Work with us → https://www.f5fp.com/

Show more...
3 months ago
7 minutes

Retire With Confidence
Outsmart the IRS: Zero Capital Gains Strategy for Retirees

What if you could sell investments in retirement and pay zero capital gains taxes? In this video, we’ll show you how retirees can take advantage of unique tax rules to legally outsmart the IRS. From understanding income thresholds to tax-efficient withdrawals and smart portfolio planning, you’ll discover strategies that can keep more money in your pocket.

If you’re planning for retirement, minimizing taxes is just as important as growing your investments. Watch until the end to learn how to use the Zero Capital Gains Strategy to protect your wealth and enjoy more freedom in retirement.

Work with us → https://www.f5fp.com/

Show more...
3 months ago
9 minutes

Retire With Confidence
How Tax-Loss Harvesting Can Save You Big Money

Did you know you can use the stock market to lower your tax bill? In this video, we’ll explain how tax loss harvesting works and how it could save you thousands of dollars in taxes each year. You’ll learn the step-by-step process, when it makes sense, and the common mistakes to avoid.

Whether you’re an investor looking to maximize after-tax returns or planning for retirement, understanding tax loss harvesting can be a powerful tool in your financial strategy. Make sure to watch until the end to see how you can apply this strategy in your own portfolio.

Work with us → https://www.f5fp.com/

Show more...
3 months ago
8 minutes

Retire With Confidence
The Conservative Stock Market Strategy That Works

Is investing in the stock market a conservative approach to reaching your goals? In this video, we’ll break down conservative stock market investing for long-term goals. Protecting your purchasing power over multiple years of retirement is the goal of many investors, they just don’t know it. We are going to flip what traditional investing education teaches about how you should invest more “conservatively” as you age on its head! Do you really need bonds in your long-term investment portfolio? Can bonds maintain your purchasing power against inflation?

Wherever you are in your journey investing for your long-term goals, this video will challenge what you have been told by the talking heads about how to invest in the stock market throughout your life.

Work with us → https://www.f5fp.com/

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3 months ago
4 minutes

Retire With Confidence
How Do I Pay For Health Insurance if I Retire Early?

Retiring early sounds like a dream—but how do you actually pay for health insurance before Medicare kicks in? In this video, we break down your best options for health coverage if you’re planning to retire early. From ACA Marketplace plans to COBRA, employer retiree benefits, private insurance, and even health share programs, you’ll learn the different paths early retirees can take to protect themselves (and their savings) while enjoying the retirement lifestyle they’ve worked so hard for.

If early retirement is part of your financial plan, understanding your healthcare options is critical. Watch until the end for practical tips and strategies to lower your costs, avoid surprises, and find the best fit for your situation.

Work with us → https://www.f5fp.com/

Show more...
4 months ago
18 minutes

Retire With Confidence
Retire With Confidence is the podcast designed to help you move beyond the fear of the complexity of finances so you can be financially free to achieve personal significance. Tune in with Josh Duncan each week to turn fear into fuel that drives you into Freedom & Significance.