Stay Wealthy San Diego

Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions. But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes. In this episode, I'm simplifying the Roth conversion 5-year rule and sharing: → Why the rule is so confusing (and what most people get wrong) → The fastest way to determine how the rule applies to your specific situation → 4 real-world scenarios so you can see exactly how it works  If Roth conversions aren't a fit today, I'm also sharing one simple step everyone can take right now to make future conversions much easier. ***

Health insurance is keeping millions of Americans stuck in jobs they'd otherwise leave. In fact, 1 in 5 workers ages 50–64 say they're staying put because of their employer health coverage. And with recent changes to the ACA, that pressure is only growing.  In this episode, I cover: → Why healthcare before Medicare has become a psychological roadblock to early retirement → Why the real cost of waiting until 65 may not be what you think  → The options many people overlook and the tradeoffs worth understanding Because for most people, the healthcare challenge does have a solution. And the worst thing you can do is never explore your options at all. ***

For 30 or 40 years, a paycheck simply showed up. Then one day, it stops. Now you're staring at a portfolio and asking: "How do I turn this into reliable income for the rest of my life…without overpaying the IRS or outliving my money?"  It's no surprise so many retirees gravitate toward dividends. They feel like a replacement paycheck. In fact, the majority of investors say they prefer dividends and interest over capital gains to fund retirement. But retirement income planning isn't just about generating cash flow. It's about creating sustainable income from a finite pool of capital while coordinating taxes and the rest of your retirement plan. In this episode, I break down new research on dividend investing and explain why the most popular income strategy may be far less efficient than it appears. I also share what the evidence suggests about building a portfolio and a plan that actually supports long-term retirement success. Because when it comes to funding your retirement, small structural decisions compoun

Markets move every day. Headlines change every hour. But the greatest threat to your retirement plan isn't volatility... it's something far less visible. In this episode, I'm breaking down: → The three components of risk most investors focus on (and the one they ignore) → Why rare, extreme events have an outsized impact on long-term wealth → How to build a retirement plan designed to survive (and even benefit from) uncertainty I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the real world. ***

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers.

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 won't 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 today's episode, I break down how annuities actually work. We'll walk through the major types of annuities, how "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement. I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence. ***

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 today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead. If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio. ***

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 hasn't 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 doesn't, and how that mismatch can quietly drive taxes higher over time. More importantly, I share a planning framework couples can use while both spouses are still alive. We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse. This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement. ***

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 isn't the answer either.  So in today's episode, I break down how to think about market outlooks the right way. We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine). I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan. ***

Every January, we go through the same routine. Limits adjust, brackets shift, and most years it's just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes we've 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 why they matter. So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight. ***

After decades of saving and doing the right things, most people expect retirement to feel clear.  But for many, it doesn't. Not necessarily because they didn't 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 today's episode, you'll have a clearer framework for evaluating your retirement decisions. And more importantly, you'll understand what it actually takes to feel confident about the years ahead. ***

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun.

The Oracle of Omaha is officially "going quiet."  In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isn't about taxes, investing, or the latest market headlines. It's 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: ▶ Why he chose to say this now (at age 95!) ▶ What retirement savers and investors can learn from his message ▶ How his parting wisdom can change the way you use your time and wealth If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you. Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life. ***

"Just buy the index." It's the simple advice that built your wealth and got you to the finish line. But here's 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: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income.  ▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns.  ▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind. If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you. ***

Everyone fears running out of money in retirement—even millionaires.  What most people don't realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How to find the right balance between confidence and caution By the end, you'll see why most retirees worry far more than they need to, and how to feel confident spending your own money. ***

Sales of "traditional" long-term care insurance have fallen 92% since 2002. Meanwhile, hybrid policies have surged to over 500,000 sales a year.  But which option actually makes sense for your situation?  In this episode, I break down everything you need to know before buying long-term care insurance, including: ▶ The optimal age to purchase ▶ Traditional vs. hybrid policies (the real pros and cons beyond the sales pitch) ▶ The actual costs of proper coverage I'm also sharing three critical implementation details that can make or break your coverage when you need it most. If you're approaching retirement and wondering how to protect yourself from potentially catastrophic long-term care costs, this episode will give you the clarity you need to make an informed decision. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions

You've heard it before—70% of Americans over 65 will need long-term care. While that number is technically true, it's also misleading. Because here's what many people don't realize: the vast majority of retirees will never face a catastrophic, six-figure care event. In fact, nearly two-thirds will spend ZERO out of pocket during their lifetime!

Americans lost a record $16 billion to scams in 2024—nearly 40% from investment fraud alone. The trend is moving in the wrong direction.  In this episode, I share the story of a small-town financial advisor who built trust over decades, until that trust unraveled into one of the most devastating scams they’d ever seen. More importantly, I break down 8 red flags that experts say could indicate you're being conned. Because here’s the truth: falling for a scam doesn’t mean you’re careless or foolish—it means you’re human. And understanding the psychology behind deception is the best way to protect yourself. If you think you’re immune, that confidence might be exactly what scammers are counting on. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement’s biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you’re seeking clarity and a proven re