The Iran War, which began on February 28, 2026, is impacting global markets and I’m pretty sure it’s having an effect on your portfolio too. Over the past month, the S&P 500 has dropped about 6%, largely due to surging oil prices. With crude oil climbing as high as $100 a barrel and lingering uncertainty around the conflict's resolution, volatility is weighing heavily on retirement investments. 

We'll explore the implications for investors, discuss historical parallels with previous market shocks, and offer practical tips to navigate the fallout—whether you're looking to rebalance, automate your contributions, or take advantage of tax-loss selling. Stay tuned as I break down actionable strategies to manage your portfolio through these turbulent times and hear why it's important to avoid overreacting despite the dramatic headlines.

On the show this week, I’m talking all about the topic of probate and how adding a Transfer on Death (TOD) or Payable on Death (POD) beneficiary designation to certain assets can help you avoid your estate being tied up in the probate process. You’ll learn which types of accounts allow for TOD or POD beneficiaries, why these designations might be preferable to joint tenancy, and the pros and cons of setting them up. I break down step-ups in cost basis, the impact on estate taxes, and touch on differences across states and how to make sure your estate plan actually fits your wishes.

In the last episode, I discussed seven mistakes to avoid when filing your 2025 taxes. So, in this episode, I'm going to discuss the tax-filing mistakes people can make when filing an extension. Here are the four most common extension errors that could cost you money, including misconceptions about payment deadlines, underestimating taxes, and the importance of understanding state-specific extension rules.

Tax season is here, and if you’re just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you’re not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of your money where it belongs.

If you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention.

If you have children and you’ve been thinking, “Why wait until I’m gone to help them financially?”—this episode is for you. In Episode 294, I walk through the biggest things to consider before making gifts to your kids while you’re still alive, and I break down some of the smartest ways to do it without triggering unnecessary taxes.

I’m seeing this trend more and more with my clients, and it makes sense. Financial markets have performed well, real estate has surged, and many retirees are in a stronger position than generations before them. But just because you can gift money doesn’t mean you automatically should. There are several financial and family dynamics you need to think through first.

If you’re approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it’s easy to make a costly mistake if you don’t understand how the pieces fit together.

In this episode, I walk through the Medicare “alphabet,” explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time.

Whether retirement is right around the corner or still a few years away, this episode is designed to help you avoid penalties, coverage gaps, and surprises down the road.

The landscape of Social Security is changing yet again. As we enter 2026, six big changes will impact both current and future retirees. I break down everything from the new cost of living adjustment (COLA), increases in the earnings test limit, and updated eligibility requirements, all the way to shifts in the full retirement age and the solvency projections for the Social Security Trust Fund.

You’ll also hear practical tips on maximizing your Social Security benefits, how to prepare for what’s ahead, and why it’s more important than ever to have a solid retirement plan in place. 

Have you ever fallen victim to a RAT attack? No, not the furry kind, a Remote Access Trojan attack. 

I’m discussing how cybercriminals use social engineering to target victims, and the real-world impact these threats can have on your investment accounts and personal information. I reveal the latest tactics scammers use, and, most importantly, offer practical tips to help you recognize warning signs, safeguard your accounts, and minimize your risk, whether you’re an individual managing your retirement nest egg or a business owner overseeing company assets.

A listener recently wrote in with a common and important retirement planning question: If I’m already maxing out my 401(k), can I also contribute to a traditional IRA in the same year? The short answer is yes—but whether it makes sense, and how much benefit you receive, depends on your income, tax situation, and long-term goals.

In this episode, I break down how traditional IRA contributions work alongside employer-sponsored retirement plans, when those contributions are deductible, and what options are available if your income is too high for a deduction. We also explore alternative strategies, including Roth IRA contributions and backdoor Roth conversions, so you can decide how best to use your annual IRA “coupon.”

This episode is especially helpful if you’re trying to balance tax savings today with tax flexibility in retirement and want to avoid common mistakes that can complicate your plan later.

Last week, we covered the best investments to preserve your money, but this week we are shifting gears to focus on growth. For retirees, the goal is to have an income that outpaces inflation, and historically, the best way to achieve that is by having 50% to 70% of your portfolio invested in stock funds.

In this episode, I break down five specific Exchange Traded Funds (ETFs) that can help you grow your wealth in 2026. I discuss why I prefer ETFs over mutual funds, specifically focusing on cost, transparency, and liquidity, and provide the exact ticker symbols and expense ratios for the funds I use with my own clients to build diversified, growth-oriented portfolios.

If you are willing to accept some volatility to achieve higher long-term returns, this episode provides a blueprint for structuring the equity side of your retirement plan.

This episode is your introduction to the world of conservative investing, so it’s perfect for you if you’re looking to preserve your principal and grow your money at a steady pace. I’m walking you through seven standout investment choices for 2026, ranging from high-yield online money market accounts to short-term bond funds, CDs, and Treasury bonds.

We’ll discuss how to shop around for the best rates, the importance of keeping up with inflation in retirement, and the benefits and limitations of each strategy. There’s something here for anyone who wants their money to work a little harder without taking on unnecessary risk.

In this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress.

Whether you’re just starting your retirement planning or fine-tuning your financial strategy, this episode is full of actionable tips to help you improve your financial life in 2026. If you’re ready to take charge of your future and put a solid plan in place, this episode is a must-listen.

As we turn the calendar to 2026, I reveal my forecasts for the stock market, interest rates, and top asset classes, and take a look back at how my 2025 predictions stacked up against reality.

From the S&P 500’s rollercoaster performance to the ongoing rivalry between growth and value stocks, and even a showdown between bitcoin and gold, I break down what the numbers were, where I hit the mark, and where I missed. You’ll also hear my insights on international versus U.S. stocks, the outlook for small caps, and what the Federal Reserve might do with interest rates in the year ahead.

Get ready for smart strategies, listener thank-yous, and a dose of investing reality as I help you set expectations (and goals) for the year to come.

2025 has been a year of significant highs and lows, a bittersweet time marked by personal loss but also tremendous growth in our community of listeners and clients. As we wrap up the year, I wanted to take a moment to reflect and, more importantly, to give back by answering the most pressing questions on your minds.

In this episode, I’m tackling the top 10 most asked financial questions I received in 2025 from both clients and listeners. From the future solvency of Social Security and the reality of rising inflation to the specifics of Bitcoin and long-term care, we are covering the topics that directly impact your retirement confidence.

I also share a special thank you gift to you my listeners: a significant discount on my Retirement Readiness Review course to help you kickstart your 2026 planning. Whether you are wondering if you should pay off your mortgage or how to find a truly objective financial advisor, this episode provides the clear, direct answers you need to navigate your financial future.

529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences.

I also discuss the various tax advantages of contributing to a 529 plan, like state tax deductions, tax-deferred growth, and even the ability to roll leftover funds into a Roth IRA for your child. He offers real-life examples, highlights differences across state plans, and gives practical tips on maximizing your savings and tax benefits as the year wraps up.

If you’re looking to make the most out of your child or grandchild’s future education while being smart about your finances, this episode is packed with must-know information.

In the season of giving, we’re discussing making charitable contributions in 2025 and 2026. Americans are known for their generous donations to worthy causes, but understanding the best ways to give and maximize your tax benefits is key.

This episode covers four effective strategies for making charitable contributions, from utilizing Qualified Charitable Distributions (QCDs) from your retirement accounts to cash donations, gifting highly appreciated stock or real estate, and using donor-advised funds. I also break down recent and upcoming tax law changes that impact your ability to itemize and deduct charitable donations, ensuring you avoid common pitfalls and make the most of your generosity.

Whether you’re planning a gift this year or thinking ahead, this episode is packed with actionable tips to help you give back and plan for a successful retirement. 

Healthcare planning is a huge part of getting ready for your retirement. In this episode, I tackle one of the most pressing updates for retirees: the latest changes to Medicare premiums for 2026, including important surcharges, deductibles, and strategies to help you manage your healthcare expenses. 

I’m helping you understand the significant increases in Medicare Part B premiums and deductibles, the impact these changes will have on your Social Security benefits, and why waiting to claim Social Security might pay off.

Listen in to get helpful strategies for appealing IRMAA surcharges and practical tips for structuring your income to minimize additional Medicare costs. If you’re planning for retirement or already navigating Medicare, this episode is packed with timely advice to help you make informed decisions about your healthcare and finances.

As 2025 comes to a close, we’re here to help you make the most of year-end tax planning. I’m explaining seven actionable strategies to help you minimize your tax liability and optimize your retirement savings before the New Year. 

From maximizing retirement plan contributions and exploring Roth conversion opportunities to using donor-advised funds for charitable giving and getting the most from your health savings accounts, this episode is packed with practical advice. The insights I’m sharing in this episode will guide you through the essential moves you need to consider before December 31st.

There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I’m focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax strategies.

Tune in as I walk you through what you need to know, how to prepare for these new rules, and actionable steps to make the most of your retirement savings.