The Pilot’s Advisor Podcast
Financial and retirement planning guidance from pilot and financial advisor Ryan Fleming. The show will help you figure out how to take your financial plan from takeoff to landing with smooth sailing along the journey. We’ll teach both pilots and non-pilots what it takes to have a successful financial future. The Pilot’s Advisor Podcast® will answer your questions about 401(k)s, IRAs, taxes in retirement, long term care needs and much more.
Episodes
Thursday Mar 13, 2025
Market Corrections: Panic or Opportunity?
Thursday Mar 13, 2025
Thursday Mar 13, 2025
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
Thursday Mar 06, 2025
Should You Stay in Cash or Keep Investing in Your 401k?
Thursday Mar 06, 2025
Thursday Mar 06, 2025
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
Thursday Feb 27, 2025
Financial Lessons from the Past 6 Months & Early 2025
Thursday Feb 27, 2025
Thursday Feb 27, 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
Thursday Feb 20, 2025
America Has a Major Retirement Savings Problem
Thursday Feb 20, 2025
Thursday Feb 20, 2025
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
Thursday Feb 13, 2025
Retirement Lessons from Andy Reid: Super Bowl-Worthy Financial Strategies
Thursday Feb 13, 2025
Thursday Feb 13, 2025
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
Thursday Feb 06, 2025
Market Timing vs Active Trading
Thursday Feb 06, 2025
Thursday Feb 06, 2025
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
Thursday Jan 30, 2025
DeepSeek Market Volatility: What Investment Lessons Can We Learn?
Thursday Jan 30, 2025
Thursday Jan 30, 2025
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
Thursday Jan 02, 2025
The #1 Investing Lesson For Pilots From 2024
Thursday Jan 02, 2025
Thursday Jan 02, 2025
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
Thursday Dec 26, 2024
The 4 Things Financial Advisors Wish Every Pilot Knew
Thursday Dec 26, 2024
Thursday Dec 26, 2024
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
Thursday Dec 19, 2024
Is Timing Your 401k Contributions As Bad As Timing The Market?
Thursday Dec 19, 2024
Thursday Dec 19, 2024
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