The Pilot’s Advisor Podcast

Retirement Lessons from Andy Reid: Super Bowl-Worthy Financial Strategies

Fresh off another Super Bowl appearance, Andy Reid is a legendary head coach known for his strategic brilliance and leadership in the NFL. But what if we told you that his insights could also apply to financial planning and retirement strategies? In our latest podcast episode, we’ll share four bits of wisdom from Andy Reid draw parallels between his coaching philosophy and essential financial lessons. 
Here’s what we cover in this episode:
0:00 - Intro
2:20 – Quote 1
3:49 – Quote 2
4:58 – Quote 3
7:23 – Quote 4
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 Timing vs Active Trading

This video explains why trying to time the market is a risky and often costly strategy for investors. It highlights how emotional decision-making, fear, and greed lead to buying high and selling low—hurting long-term returns. Historical data shows that missing just a few of the market’s best-performing days can drastically reduce overall gains. Instead of market timing, experts emphasize the benefits of a disciplined, long-term investing approach focused on diversification and staying invested.
The key takeaway: time in the market beats timing 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

DeepSeek Market Volatility: What Investment Lessons Can We Learn?

The stock market saw a huge pullback in the technology sector with the arrival of DeepSeek, a new Chinese AI platform. What lessons should we be learning from what’s happening in the market and how does this change investment strategies?
Today we’re joined by Lee Hyder of Lee Hyder & Associates to discuss the emotional reactions that often accompany such news and how they can lead to impulsive decisions among investors.
Here’s what we cover in this episode:
0:00 – DeepSeek market pullback
3:00 – What did we learn?
7:12 – One powerful lesson to remember
10:38 – Strategies for 2025
12:37 – Emotional decisions
18:08 – DIY investors
23:09 – Are you aggressive enough?
26:47 – Evolving with technology
32:21 – Fees vs Returns
 
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

The #1 Investing Lesson For Pilots From 2024

Ryan Fleming, The Pilot’s Advisor, shares the #1 lesson he learned about investors in 2024: successful investing isn’t sexy or flashy.
Forget stock picking, market timing, or chasing the next big thing. Ryan explains why disciplined, diversified investing is the real key to long-term wealth—and how trying to “get rich quick” often leads to losing it all.
 
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

The 4 Things Financial Advisors Wish Every Pilot Knew

Imagine you could read your financial advisor’s mind before you even walked through the door for the first time. What would they want you to know? In this episode, we bring you the game-changing insights financial pros wish every saver and investor understood.
Discover the four crucial insights that can transform your retirement planning and investment strategy. From understanding real risk potential and the motivations behind financial information to the value of long-term planning and the comprehensive nature of financial planning beyond just investments, this episode can benefit pilots at any stage of their career.
Here’s what we cover in this episode:
0:00 – Intro
1:17 – Real risk potential
3:20 – Understanding the motivation of information
5:56 – The value of long-term planning
7:05 – More than just investments
 
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 Timing Your 401k Contributions As Bad As Timing The Market?

In this episode, we dive into the question of timing 401k contributions and whether it’s as risky as timing the market. The discussion explores strategies for maximizing contributions, including the pros and cons of contributing early versus waiting for market conditions to improve. Key topics include the impact of market volatility, the importance of long-term investing, and why dollar-cost averaging can be a smart approach. Ultimately, the goal is to ensure you’re consistently maximizing your 401k to take full advantage of retirement savings, regardless of market fluctuations.
Here’s what we cover in this episode:
0:00 - Intro
0:32 – Investing is for the long-term
1:12 – Maxing out your 401k
 
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
 

How Retirement Planning is Different For Gen X

When we start talking about Generation X and Millennials and how their planning is going to be different from Baby Boomers, we have some pretty significant adjustments to make. If you haven’t evolved with the changing financial world we live in, then you need to check out this video with Ryan.
Join us to learn about the critical need for embracing technology and AI in managing investments. The days of passive strategies and simply building a diversified portfolio are being challenged by the rapid advancements in trading technologies and the increasing complexity of financial markets. If you’re a Gen X pilot who wants to be as prepared as possible, check out today’s show.
 
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 Volatility: When Should You Start To Worry?

People are often told not to worry about a market crash when they’re younger because time is on their side, but what happens when you no longer have the benefit of a long time horizon? Should you take the threat of a market correction or crash differently?
In today’s episode, Ryan shares insights on the importance of understanding time horizons over age and highlights the common pitfalls pilots face, such as over-reliance on the S&P 500.
Here’s what we cover in this episode:
0:00 - Intro
1:41 – At what age do you need to worry about a market crash?
3:45 – The average employee vs. pilots.
7:15 – Closing thoughts
 
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

How The Fed Rate Cut Impacts Money Market Funds

Money market funds have been a go-to option for many pilots, especially during periods of rising interest rates. They offered a seemingly safe haven with attractive returns compared to traditional savings accounts. However, as the Fed begins to cut rates, the allure of these funds is being questioned.
Today we’ll share insights on whether these funds still hold value in today's economic landscape.
Here’s what we cover in this episode:
0:00 - Intro
1:04 – Will money market funds lose popularity?
3:08 – Outpacing inflation
4:05 – Retirement toolkit
 
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

Can You Live Off Dividends?

Let’s tackle a question that many retirees ponder: Is living off dividends a viable retirement income strategy? Investors will often look to dividends as a source of income in retirement so let’s talk about the potential pitfalls and benefits of relying solely on dividend-paying stocks.
Tune in as Ryan explains the role of dividend investing in his eyes and shares other strategies to consider when it comes to funding your retirement. Dividends are just one tool you can utilize to reach your income goals so understanding the various strategies is essential in planning.  
Here’s what we cover in this episode:
0:00 - Intro
1:56 – Other strategies to consider
2:48 – Closing thoughts
 
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