Today I'm discussing the biggest retirement investment risk.

As Morgan Housel put it, "It's the hardest risk for people to understand... 

...and it's the only one that really matters."

In this episode, you'll learn:

► What the three sides of risk are

► Why tail risk is all that matters

► How to mitigate this risk in your retirement plan

You'll also learn why most investors should (probably) stay away from investment products promising you lots of upside with limited downside. 

***

2025 TAX CHEATSHEET

Subscribe to the Stay Wealthy Retirement Newsletter!

As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF). 

You'll also receive weekly retirement and investing tips from yours truly.

👉 Click here to subscribe and grab your cheatsheet.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Worried about Medicare IRMAA eating into your retirement savings? 

Whether you're 10+ years away from Medicare or already enrolled, this episode will help you navigate this pesky surcharge and protect your retirement savings.

Key topics covered:

► Updated 2025 IRMAA brackets 

► Answers to common planning questions 

► 3 strategies to minimize (or avoid) IRMAA

You'll also learn how to project future IRMAA brackets for better planning.

If you want a clear roadmap for making informed decisions about your future healthcare costs, you'll enjoy today's episode.

***

RETIREMENT & TAX PLANNING:

Looking to hire a financial planner with retirement & tax planning expertise?

My team and I only have a few more openings for Discovery Meetings with new clients. 

If you're seeking professional help, we would love to have a conversation!

👉 Learn more about our process and grab one of the remaining slots.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Markets tend to operate in cycles—yesterday's winners often become tomorrow's losers (and vice versa). 

The most unloved asset classes can quietly become the best performers, while the most popular ones frequently disappoint.

Yet, many investors fall into the trap of assuming recent trends will continue indefinitely.

But markets don’t work that way.

No asset class outperforms or underperforms forever.

To help you avoid falling into this trap (and make more informed portfolio decisions), I’m sharing key takeaways from Vanguard's 2025 Market & Economic Report in this episode. 

I’m also sharing 5 actions retirement savers can take right now to prepare for success over the next decade and beyond.

***

Looking to hire a financial planner with retirement & tax planning expertise?

My team and I only have a few more openings for Discovery Meetings with new clients. 

If you're seeking professional help, we would love to have a conversation!

👉 Learn more about our process and grab one of the remaining slots.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Looking to hire a financial planner with retirement & tax planning expertise?

My team and I have availability for 25 Discovery Meetings over the next 8 weeks.

If you're seeking professional retirement planning help, we would love to have a conversation!

👉 Learn more about our process and grab one of the 25 meeting slots.

We intentionally limit the number of new clients we take on each year.

This ensures we can provide each family with highly customized investment, retirement, and tax planning services.

Once these 25 meetings are scheduled, we will not have availability to meet with new clients until later this year.

Schedule your Discovery Meeting.

***

Today I'm sharing the essential steps for evaluating and selecting the right financial advisor for your unique situation. 

Specifically, I cover 5 important things:

► How to identify and document your financial challenges, needs, and goals before starting your search

► Critical questions to ask yourself about the type of professional you want

► Guidance for conducting background checks

► Non-obvious questions to ask potential advisors

► The importance of a well-defined evaluation process (and why you shouldn't rush your decision)

You'll learn how to navigate through the sea of 300,000+ financial advisors to find the right one for you.

Whether you want a short-term or long-term engagement, this episode provides actionable steps to help you make the right choice.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Grab your Tax Planning Cheatsheet (updated for 2025!) by clicking here.

The 2-page PDF guide includes every important number you'll need for your retirement & tax planning next year.

Updated federal income tax brackets, AMT annual limits, standard deductions, Social Security taxation summary, estate and gift tax annual limits…and more.

👉 Download it now. 

***

In our final episode of the year, I'm taking a break from the usual nerdy retirement planning talk to share twelve (12) insightful, fun, and humourous investing statistics. 

These stats cover topics such as:

➤ The McRib Effect: Can a fast-food favorite influence markets?

➤ Shiller P/E Ratio History: What does this popular valuation signal suggest for the market's future?

➤ Netflix Drawdowns: A stock’s wild history of recovery.

➤ Berkshire Hathaway: A long-term (unbelievable) investment story unfolds.

➤ Pet Spending: A surprising shift in American priorities.

Whether you’re a market enthusiast or just here for the entertaining stories, you’ll love this lighthearted yet insightful end-of-year episode.

Thank YOU for making this year so special by tuning in and engaging with the show.

Enjoy the holidays, reflect on the year behind us, and prepare to dive into 2025 with fresh market insights and retirement planning strategies. 

Here’s to "staying wealthy" next year and beyond! 🎉

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

How do we fix the housing affordability problem in the U.S.?

Will lower interest rates really improve the real estate market?

How have Zillow and Airbnb contributed to the current housing challenges?  

What are tariffs (+ benefits and drawbacks)?

What's next for the U.S. economy? 

These are just a few of the questions I'm exploring in this episode with author and economic expert, Kyla Scanlon. 

***

BOOK GIVEAWAY

I'm giving away 10 copies of Kyla's beautifully written and designed book, "In This Economy? How Money & Markets Actually Work."

To put your name in the hat and receive a free copy, be sure you're subscribed to the Stay Wealthy Retirement Newsletter by visiting https://www.youstaywealthy.com/email.

Next week, my team will randomly select 10 lucky readers to give our copies away to. 

👉 Join the newsletter!

***

FREE RETIREMENT PLANNING RESOURCES:

As a bonus for subscribing to the Stay Wealthy Retirement Newsletter, you'll also receive three (3) of my MOST popular retirement & tax cheatsheets. 

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Today, I’m discussing the challenges of spending money in retirement. 

To help, Brian Portnoy, one of the world’s leading experts on the psychology of money, joins us to discuss three big things:

➤ Why it’s so difficult for retirement savers to transition from saving to spending

➤ What you can do to prepare for the (well-documented!) challenges of retirement spending 

➤ How to use Brian’s “Four C’s” to achieve true wealth in retirement

We also delve into the meaning behind Brian’s famous quote, “Diversification always means having to say your sorry,” and how it can help you make better investing decisions.

***

FREE RETIREMENT PLANNING RESOURCES:

Subscribe to the Stay Wealthy Retirement Newsletter!

As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets. 

You'll also receive my weekly retirement newsletter!

👉 Click here to subscribe and grab your cheatsheets.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Emerging Markets are the world’s primary drivers of global growth (and wealth accumulation).

Just over 50% of the world's economic output comes from these countries. 🤯

They play a crucial role in shaping global economic trends...

...but most retirement investors don't fully understand this asset class.

To help break it down for us, Emerging Markets expert and founder of Life + Liberty Indexes, Perth Tolle, stops by to discuss: 

➤ What Emerging Markets are and why retirement savers should consider investing in this asset class

➤ Why traditional, low-cost Emerging Market funds may produce lower returns

➤ The pros/cons of excluding countries like China and Russia from an Emerging Markets fund 

We also discuss why "freedom" plays an important role in this asset class and how investors can (potentially) use freedom metrics to capture higher returns. 

***

FREE RETIREMENT PLANNING RESOURCES:

Subscribe to the Stay Wealthy Retirement Newsletter!

As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets. 

You'll also receive my weekly retirement newsletter!

👉 Click here to subscribe and grab your cheatsheets.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Why are most people planning for the wrong things in retirement?

What should they be planning for that they’re not?

To help answer these important questions, Psychologist & Behavioral Finance Expert Dr. Daniel Crosby stops by to discuss:

➤ What our happiness is determined by

➤ Why (contrary to popular research) more money can ACTUALLY make us happier

➤ What is the “PERMA model” and how can we use it to improve retirement success

We also discuss why retirees are more depressed than everyone else and what they can do to mitigate this risk.

***

THE SOUL OF WEALTH: 

Grab a copy of Daniel's new book, The Soul of Wealth. 

The book explores what wealth really is and provides practical suggestions for how to change your thinking and your actions in small, powerful ways, for a wealthier life.

***

FREE RETIREMENT PLANNING RESOURCES:

Subscribe to the Stay Wealthy Retirement Newsletter!

As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets. 

You'll also receive my weekly retirement newsletter!

👉 Click here to subscribe and grab your cheatsheets.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network

Today, I'm talking about navigating the risks of concentrated investments.

Specifically, Peter Lazaroff, CIO of Plancorp, joins me to answer three BIG questions:

➤ How do you know if you have a "concentrated investment?"

➤ What are some little-known risks investors aren't considering?

➤How do you (tax-efficiently) diversify concentrated investments?

I also share a specific exercise investors can follow to decide if they should sell some or all of their concentrated holding(s).

***

FREE RETIREMENT PLANNING RESOURCES:

Subscribe to the Stay Wealthy Retirement Newsletter!

As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets. 

You'll also receive my weekly retirement newsletter!

👉 Click here to subscribe and grab your cheatsheets.

***

EPISODE RESOURCES:

📊  Get Your FREE Retirement & Tax Analysis!

✏️  Grab the Episode Show Notes

📘  Check Out the Retirement Podcast Network