3 Tax Planning Strategies Most Retirement Investors Overlook
Stay Wealthy Retirement Podcast
Release Date: 12/11/2025
Annuities Explained: When Guarantees Helpâand When They Hurt Your Retirement
Stay Wealthy Retirement Podcast
Annuities are often sold as a simple solution to a complicated retirement problem. Guaranteed income. Protection from market volatility. Peace of mind that your money wonât run out. But behind those promises is a much more complex set of trade-offs that many investors don't consider. Because while annuities can play a role in retirement planning, evaluating them in isolation often leads to unintended consequences (higher fees, reduced flexibility, extra taxes). So in todayâs episode, I break down how annuities actually work. Weâll walk through the major types of...
info_outline
The Best Investment for Your Retirement (Itâs Not What You Think)
Stay Wealthy Retirement Podcast
What makes an investment "good?" It seems like a straightforward question, but the answer is more subjective than most people realize. Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made. Hearing it framed that way struck a different chord. And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely. In todayâs episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some...
info_outline
What Happens to Your Taxes When a Spouse Dies (And How to Plan Ahead)
Stay Wealthy Retirement Podcast
After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away. But for many surviving spouses, the first surprise is a higher tax bill, even when income hasnât changed much. In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse. Using a real-world example, I show why tax brackets shrink, why retirement income often doesnât, and how that mismatch can quietly drive taxes higher over time. More importantly, I share a planning framework couples can use while both...
info_outline
How to Use 2026 Market Outlooks to Plan for Retirement
Stay Wealthy Retirement Podcast
Every year, Wall Street rolls out its market predictions. Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away. But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers. Because, while short-term forecasts are usually noise, ignoring market expectations altogether isnât the answer either. So in todayâs episode, I break down how to think about market outlooks the right way. Weâll cover why forecasts so often miss the mark, when long-term...
info_outline
2026 Tax Changes Explained (Including 2 Rules Causing Confusion)
Stay Wealthy Retirement Podcast
Every January, we go through the same routine. Limits adjust, brackets shift, and most years itâs just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes weâve seen in a while. And buried inside those updates are two new rules that have already caused widespread confusion (even among experts). In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan. I also also break down those two unique rules, sharing how they work, who they apply to, and...
info_outline
The 7 Questions That Shape a Confident Retirement
Stay Wealthy Retirement Podcast
After decades of saving and doing the right things, most people expect retirement to feel clear. But for many, it doesnât. Not necessarily because they didnât save enough, but because key financial decisions were made in isolation. In this episode, I walk through the seven questions every retirement saver should be able to answer. I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way. By the end of todayâs episode, youâll have a clearer framework for evaluating your retirement decisions. And more...
info_outline
7 Investing Facts Every Retirement Saver Needs to Hear
Stay Wealthy Retirement Podcast
Itâs that time of year againâtime to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives⊠and have a little fun. đ In this annual âsurprising statsâ episode, Iâm sharing 7 counterintuitive facts about the markets and investing. Some are counterintuitive. A few might make you question things youâve believed for years. And at least one involves math that should make anyone considering complex insurance products hit the pause button. By the end of todayâs episode, youâll walk away feeling more confident in the proven...
info_outline
3 Tax Planning Strategies Most Retirement Investors Overlook
Stay Wealthy Retirement Podcast
đ„ Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): *** Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity. But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced. In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill. You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions. If you're nearing...
info_outline
âHappy Thanksgiving (Yes, Even the Jerks)â: Wisdom from Warren Buffett
Stay Wealthy Retirement Podcast
The Oracle of Omaha is officially âgoing quiet.â In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isnât about taxes, investing, or the latest market headlines. Itâs about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scoreboard stops moving. In this Thanksgiving special, I break down: ⶠWhy he chose to say this now (at age 95!) ⶠWhat retirement savers and investors can learn from his message â¶...
info_outline
The S&P 500 Trap: Why the "Safe" Choice Is Actually Risky for Retirees
Stay Wealthy Retirement Podcast
"Just buy the index." Itâs the simple advice that built your wealth and got you to the finish line. But hereâs what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episode, we cover: ⶠThe Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ⶠS&P 500 Reality Check: Why the "safe" default option is...
info_outlineđ„ Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet
***
Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity.
But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced.
In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill.
You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions.
If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead.
***
đ SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:
For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirementsâfrom tax strategies and investments to income and legacy planning.
The result?
Less stress. Lower taxes. More confidence about the future.
If youâre looking for clarity and a proven, personalized process, weâd be honored to have a conversation.
đ Click Here to Schedule a Call
***
EPISODE RESOURCES:
â Download the 2026 Tax Cheat Sheet
â Grab the Episode Show Notes
â Join the Stay Wealthy Retirement Newsletter