Stay Wealthy Retirement Podcast

At 63, David has $4 million saved.
Two advisors have told him he's ready to retire, and every Monte Carlo simulation agrees... but he still can't bring himself to do it.
"I'm no longer being smart," he admits. "I'm just scared to pull the trigger."
The uncomfortable part is that no number may fix this, because what's holding David back was never on the spreadsheet.
In this episode, I'm joined by Daniel Crosby, Ph.D. — a psychologist and behavioral finance expert — to answer listener questions about the part of retirement the math can't solve. 
You'll learn:
→ How to spend in retirement so the enjoyment doesn't wear off so fast
→ A 3-part framework for putting your money where it creates the most happiness
→ When changing your plan is wise, and when it's just reacting to noise
→ The 2 questions to ask when you're financially ready but still can't pull the trigger
→ What actually moves the 40% of your happiness that's within your control
By the end, you'll have a clearer way to separate a plan that works on paper from a retirement you actually feel ready to live.
***
📆 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™

Imagine I hand you two mutual funds and ask how you'd split your money.
Same holdings. Same cost. Line by line, they're the exact same fund.
The only difference?
One has a name you recognize and the the other is generic. 
Financially, there's no reason to prefer one over the other. 
But when researchers ran this experiment, investors didn't split their money evenly.
In this episode, I break down new research on the hidden cost of making investment decisions based on familiarity.
Here's what you'll learn:
→ Why a familiar fund name changes how investors judge risk, return, and safety 
→ What the "trust premium" reveals about how investors value familiarity
→ How famous fund families have performed against their benchmarks
→ The questions to ask before choosing a fund or accepting an advisor's recommendation
By the end, you'll have a more disciplined and informed way to judge whether confidence is being earned or merely assumed.
***
📆 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™

You spend 30 or 40 years protecting your future self.
Then you finally retire... and the person you were saving for never quite arrives.
There's always an older version down the road who still feels like they need protecting.
So you keep saving for tomorrow while postponing the life you could enjoy today.
But more money for "future you" isn't what makes retirement better.
In this episode, Hal Hershfield, Ph.D. — a UCLA professor of Behavioral Decision Making and author of Your Future Self — joins me to explain why.
Here's what you'll learn:
→ Why your brain treats your future self like a stranger (and how that shapes every money decision)
→ How "projection bias" distorts irreversible choices like when to retire or claim Social Security
→ The "denominator problem" that stops retirees from spending + a simple reframe to help
The distance we feel from our future selves is real and well-documented. 
It is also, with the right perspective, something we can learn to close.
***
📆 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™

When inflation makes headlines, it can feel like one of those retirement risks you just have to endure.
Saving, investing, tax planning, income strategy... those are levers you can pull.
Rising prices feel different. They feel like something that happens to you.
But the inflation number you see in the news is rarely the number that matters most for your retirement plan.
Two retirees can live through the same inflation environment and face very different risk — and the gap between them often comes down to a few things they can actually control.
In this episode, I'm simplifying how retirement savers should think about inflation.
You'll learn:
→ The 3 questions that reveal your true inflation risk
→ Why headline inflation can mislead retirees in both directions
→ How to protect your income, spending power, and retirement confidence
A strong retirement plan doesn't require a perfect inflation forecast.
It just needs to be built for the reality that uncomfortable periods will happen, and prepared for them before they arrive.
***
📆 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™

Umbrella insurance isn't usually the first thing people think about when they picture retirement planning.
Most conversations focus on saving enough, investing well, reducing taxes, and creating income.
But in retirement, one unintentional accident can create a very different kind of risk.
Not just a temporary setback, but a threat to savings you may no longer have decades to rebuild.
In this episode, I'm simplifying how umbrella insurance works for retirement savers.
Specifically, I'm sharing:
→ Why liability risk doesn't necessarily disappear after your working years
→ What umbrella insurance does and doesn't cover
→ 5 common mistakes people make when buying or reviewing a policy
→ A simple 4-part formula for estimating how much coverage you actually need
You'll also learn why the common "match coverage to net worth" rule can be misleading + why coverage may still make sense even when the math says you don't technically need it.
***
📆 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™