Podcast Episodes
Back to SearchWhy a Stock Market Crash Won't Ruin Your Retirement (and What Actually Will)
Episode 270
Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.
See how they fit together in one…
4 months, 2 weeks ago
Annuities Explained: When Guarantees Help—and When They Hurt Your Retirement
Episode 269
Annuities are often sold as a simple solution to a complicated retirement problem.
Guaranteed income. Protection from market volatility. Peace of min…
4 months, 3 weeks ago
The Best Investment for Your Retirement (It's Not What You Think)
Episode 268
What makes an investment "good?"
It seems like a straightforward question, but the answer is more subjective than most people realize.
Recently, my …
5 months ago
What Happens to Your Taxes When a Spouse Dies (And How to Plan Ahead)
Episode 267
After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away.
But for …
5 months, 1 week ago
How to Use 2026 Market Outlooks to Plan for Retirement
Episode 266
Every year, Wall Street rolls out its market predictions.
Targets get published, expectations get set, and the headlines make it sound like the futur…
5 months, 2 weeks ago
2026 Tax Changes Explained (Including 2 Rules Causing Confusion)
Episode 265
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.
Sweepi…
5 months, 2 weeks ago
The 7 Questions That Shape a Confident Retirement
Episode 264
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 t…
5 months, 3 weeks ago
7 Investing Facts Every Retirement Saver Needs to Hear
Episode 263
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…
6 months, 1 week ago
3 Tax Planning Strategies Most Retirement Investors Overlook
Episode 262
💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet
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Most year-end tax advice is generic... max …
6 months, 2 weeks ago
"Happy Thanksgiving (Yes, Even the Jerks)": Wisdom from Warren Buffett
Episode 261
The Oracle of Omaha is officially "going quiet."
In a rare and deeply personal announcement, Warren Buffett published what appears to be his final p…
7 months ago