The Pilot’s Advisor Podcast

April Fool’s: Beliefs That Fool Retirement Savers The Most

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. Ryan unpacks the financial “pranks” people may fall for—from too-good-to-be-true returns to myths about Social Security, taxes, and healthcare in retirement.
Here’s what we cover in this episode:
💸 Healthcare costs are no joke in retirement
📉 How taxes fool more people than they realize
🧠 Why “guaranteed returns” are a red flag
🪙 Dividend chasing can backfire
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Bracket Picks and Stock Myths

When it comes to investing, are you picking winners or just playing favorites? In this episode, Ryan breaks down how our emotional biases, gut instincts, and misplaced confidence can sabotage even the best financial intentions.
Using bracket-building and sports betting as a metaphor, Ryan explores how chasing individual stocks is a lot like guessing tournament upsets: unpredictable, addictive, and often disappointing.
Here’s what we cover in this episode:
🧠 Why emotional investing leads to poor decisions
📉 The surprising odds of stock-picking success
📈 Why diversification still beats “gut feeling”
⚠️ The hidden risks of being loyal to one stock
📚 How real market data can reframe your mindset
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Retirement Lessons From The Masters

What does Augusta National have in common with your retirement plan? A lot more than you think. Ryan uses the game of golf—and the iconic Masters Tournament—as a powerful metaphor for achieving retirement success. We drive into key takeaways, like why consistency leads to better retirement results as opposed to risking it all for a “hole-in-one” and how diversification is just like using a full set of clubs.
Here’s what we cover in this episode:
🏌️‍♂️ Chasing “hole-in-one” hot stocks won’t win retirement
🧰 You need a full set of clubs – Diversify your investments & tax strategies
⚠️ Avoid the hazards – Taxes, inflation, and healthcare costs can derail your plan
🧠 Your advisor is your caddy guiding you through tough shots with clarity
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Market Shoots Up on 90-Day Pause on Tariffs

If there’s ever been a great example of why you stay invested and avoid trying to time the market, it would be these recent market movements from tariff news. After days of sharp declines, the announcement that there will be a 90-day pause on tariffs for 75 countries and increased pressure on China led to an instantaneous pop upwards.
In this quick update, we’ll discuss how emotional decision-making can derail a portfolio and the hidden risks of going to cash. Every day of big gains or sharp losses is a reminder of the power of discipline and the cost of hesitation.
Here’s what we cover in this episode:
💸 Why going to cash too early can cost you big
🧭 Lessons from COVID, 2008, and other major downturns
📆 Why 2025 might finish stronger than you think
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Markets Plunge on Trump Tariff News – How Should You Invest?

The news of Trump’s tariffs has caused global markets to go into a tailspin, and that means panic has started to set in for many investors. Seeing red numbers across your portfolio is never easy, but what if you saw this as an incredible opportunity rather than a time to get out of the market?
Today we’ll talk about how long-term investors can use these dips as a chance to increase contributions and take advantage of short-term volatility.
Here’s what we cover in this episode:
📉 Market downturns = buying opportunities for the long-term
💰 Increase contributions during market dips to maximize growth
🛑 Don’t let panic lead to rash decisions
🧳 Plan for sequence of returns risk and the impact of market volatility on retirement
 
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Is 2025 A Bad Time To Retire?

Is 2025 a bad year to retire? With headlines swirling about market volatility, federal layoffs, and a possible recession, it’s a question many pre-retirees—especially pilots—are asking. If you were targeting this year for a retirement date, let’s find out if Ryan thinks pilots should still retire or put their plans on hold.
Here’s what we cover in this episode: 💼 Retirement plans should include built-in protection for volatility🔁 Diversification and risk alignment are critical pre-retirement steps🧠 Don’t make emotional decisions—stick to the plan📊 A good plan works whether the market is up, down, or sideways
 
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Market Corrections: Panic or Opportunity?

With markets off to a volatile start in 2025, many investors are feeling uneasy. But should you be worried? Ryan took a break during a recent trip to an advisor conference to share some thoughts on the recent market pullback, explaining why it’s normal, healthy, and even an opportunity for long-term investors.
If you’re concerned about the latest market turbulence, please reach out and let’s have a discussion.  
Here’s what we cover in this episode:
0:00 - Intro
1:00 – Fear and greed
3:27 – Buying opportunity
5:51 – It’s like flying
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Should You Stay in Cash or Keep Investing in Your 401k?

The thought of a market crash will often make investors rethink their portfolio and move into cash. That’s what one American Airlines pilot reached out to us about recently. He has concerns about the market so half of his 401K is in cash, but now he wants to know when he should start investing it again. Today we’re going to answer that question and have a broader discussion about the risks of trying to time the market.
Here’s what we cover in this episode:
0:00 - Intro
0:32 – Today’s question
2:50 – Changes as you approach retirement
7:22 – How investing has evolved
8:45 – Conservative doesn’t equal safe
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Financial Lessons from the Past 6 Months & Early 2025

We haven’t lacking headlines over the past six months but the craziness can provide some valuable lessons for investors. In this episode, we take a closer look at the recent fluctuations in the financial markets and the emotional responses of investors during turbulent times.
Understanding the purpose of your investments is crucial. Many investors fall into the trap of reacting impulsively to headlines, often overlooking the bigger picture of their financial goals. By focusing on long-term strategies, you can mitigate the emotional turmoil that often accompanies market fluctuations.
Here’s what we cover in this episode:
0:00 – Looking back on 2024
1:00 – Bumpy start to 2025
2:12 – Emotional reactions
4:30 – Maintaining a long-term view
6:29 – The best investors
8:58 – Understanding the market
 
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
 

America Has a Major Retirement Savings Problem

In an era where retirement depends on an individual’s ability to save, the statistics tell us that America has a real problem. Ryan saw a few stats on tv recently that raised some major concerns, and it’s time to address the root of the issues. Today we’ll share the numbers that caught our attention and talk about the steps pilots need to be taking to ensure they aren’t falling behind.
Here’s what we cover in this episode:
0:00 - Intro
1:30 – Are pilots in better shape?
3:58 – Savings tools
8:13 – Forced discipline
11:15 – Getting help
 
Retire Pilots - https://retirepilots.com
 
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
 
Pilot Tax - https://pilot-tax.com/
 
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2