The Pilot’s Advisor Podcast

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 w...

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.

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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 h...

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 vol...

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...

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.  

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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.

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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...

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:

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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. 

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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 inv...

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 ...

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.

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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 fina...

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. Ultim...

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 ...

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&...

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 episo...

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 retiremen...