Stay Wealthy Retirement Podcast

Two retirees. Same $1 million portfolio. Same 60/40 allocation. Same 4% withdrawal rate. Same 30-year retirement.
The only difference?
One retired in 1973. The other retired in 1975. 
Fast forward 30 years: one finished with about $280,000 and the other finished with over $3 million.
Same plan. Just two years apart.
In this episode, I'm breaking down new research that analyzes nearly a century of market history to answer a question most retirement plans don't spend enough time on:
"How much does your exact retirement date shape the outcome of your plan?"
Here's what you'll learn:
→ Why retirement timing may matter more than your withdrawal rate or asset allocation 
→ Why a larger nest egg at retirement has historically led to worse outcomes
→ A 3-part playbook, in priority order, for protecting your plan when the starting point looks unfavorable
Most retirement strategies focus on what happens after you retire.
But this research suggests the year you walk away from work may deserve a much bigger seat at the planning table.
***
📆 BOOK A CALL WITH OUR TEAM:
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.
👉 Learn More and Book a Call
***
EPISODE RESOURCES:
→  Grab the Episode Show Notes
→ Join the Stay Wealthy Retirement Newsletter
→  Learn About the Total Retirement System™

Many retirement savers assume the anxiety will lift once they hit a certain number.
Maybe it's $1 million. Maybe $2 million. Maybe $5 million or more.
And then the account crosses the line, the headlines turn ugly, and the worry is still there.
A recent Wall Street Journal headline put it bluntly: "Even Rich Retirees Fear Outliving Their Money."
In this episode, I'm sharing new research from Fidelity that helps explain why having "enough" so often still doesn't feel like enough.
I'm also sharing the four things I consistently see in retirees who feel genuinely secure. 
Here's what you'll learn:
→ The retirement planning factor that more than doubles confidence
→ A cognitive concept that explains why retirement anxiety has very little to do with your account balance
→ The question many well-prepared retirees still can't answer — and why ignoring it can be so costly
Not one of the four pillars has anything to do with the size of your portfolio.
Which raises the real question: what's actually keeping wealthy retirees up at night?
***
📆 BOOK A CALL WITH OUR TEAM:
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.
👉 Learn More and Book a Call
***
EPISODE RESOURCES:
→  Grab the Episode Show Notes
→ Join the Stay Wealthy Retirement Newsletter
→  Learn About the Total Retirement System™

The math behind "wait until 70" for Social Security is real.
Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%.
So why would anyone walk away from a number that big?
The short answer is that the standard break-even analysis only measures one variable. 
And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensive decision than it looks.
In this episode, I'm turning the mic over to Josh Rendler — a partner at our firm — who walks through a case study of a 62-year-old woman with a $1.5 million IRA and the question most retirees are wrestling with.
Here's what you'll learn:
→ The reframe that makes "wait until 70" fall apart for retirees with healthy pre-tax balances
→ How Social Security timing and Roth conversions compete for the same bracket space (and why claiming earlier can actually EXPAND your conversion runway)
→ The planning window that opens at 61, and what gets harder to fix once it closes
The biggest claiming-age check isn't always the biggest after-tax outcome.
And a well-built plan shouldn't make you choose between doing the math right and actually enjoying the retirement you spent 35 years earning.
***
📆 BOOK A CALL WITH OUR TEAM:
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.
👉 Learn More and Book a Call
***
EPISODE RESOURCES:
→  Grab the Episode Show Notes
→ Join the Stay Wealthy Retirement Newsletter
→  Learn About the Total Retirement System™

Tax season is finally over.
The returns are filed, the stress is behind you, and the last thing you probably want to do is think about taxes again.
But the weeks right after tax season are one of the most valuable windows you have all year.
Every number from last year is fresh, every missed opportunity is still visible, and every mistake you just uncovered is a clue about what to fix going forward.
In this episode, I sit down with Josh Rendler, CFP®, a partner at our firm and someone who spends his days deep inside client tax returns.
Together, we're answering some of the biggest questions we're hearing from retirees right now.
Here's what you'll learn:
→ The 3 numbers on last year's return that reveal your biggest 2026 planning opportunities
→ How to know if charitable giving belongs in your plan (plus the QCD detail that keeps it "invisible" to the IRS)
→ A fresh, counterintuitive take on Social Security timing
While last year's return is still on your desk: what's hiding in there that could make 2026 better? 🤔
***
📆 BOOK A CALL WITH OUR TEAM:
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.
👉 Learn More and Book a Call
***
EPISODE RESOURCES:
→  Grab the Episode Show Notes
→ Join the Stay Wealthy Retirement Newsletter
→  Learn About the Total Retirement System™

One of the biggest decisions you'll make in your 70s and 80s has nothing to do with your portfolio.
It's not about Social Security timing. And it's not about Roth conversions.
It's about where you'll live and, more importantly, how care will be delivered, coordinated, and paid for if your health changes later on.
Most people think of this as a lifestyle decision.
But in reality, it's a housing-and-care decision, and it's one most retirement plans barely address.
In this episode, I'm breaking down the later-life housing choices most retirement savers haven't fully thought through.
Here's what you'll learn:
→ The four main housing options later in life—and how they differ in cost, care, and flexibility
→ What Continuing Care Retirement Communities (CCRCs) actually are (+ a little-known tax planning tip)
→ The four types of risk every housing decision really involves
→ When this decision usually needs to be made, and what can happen if you wait too long
Because "we'll just stay in the house" isn't a plan...it's an assumption. And assumptions tend to get tested at the worst possible moment.
***
📆 BOOK A CALL WITH OUR TEAM:
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.
👉 Learn More and Book a Call
***
EPISODE RESOURCES:
→  Grab the Episode Show Notes
→ Join the Stay Wealthy Retirement Newsletter
→  Learn About the Total Retirement System™