The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots

The kids may be heading back to class, but it’s not a bad time for adults to hit the books too, especially when it comes to retirement. So, let’s test your knowledge with a quick financial pop quiz and see how ready you really are.

Here are the quiz questions for today:

📝 At what age do you get full Social Security if born after 1960?
 📝 Max IRA contribution for those 50+ in 2025?
 📝 Which retirement account requires RMDs?...

This week, Scott sits down with Jason Watson from WCG CPAs and Advisors to talk about the top 3 mistakes high-income pilots should avoid when investing in rental properties. As pilots and other high earners look for ways to diversify their income beyond their primary careers, rental properties offer a powerful path to building lasting wealth- if you approach it the right way.

Here’s some of what we discuss in this episode:

🛫 Why pil...

We’re back for Part 2 of the “7 Deadly Sins of Investing,” and these final three may be the hardest to overcome, because they’re not technical; they’re emotional. Scott explores how fear, greed, and impatience can quietly creep into our financial decisions and derail long-term success. These aren’t just feelings; they’re patterns that lead to poor timing, unnecessary risk, and abandoning a perfectly good plan.

Here’s some of what we...

We’re kicking off a special two-part series on the “7 Deadly Sins of Investing.” In this first installment, Scott unpacks four of the biggest behavioral missteps investors make, especially when emotions run high or market headlines dominate the news. If you're over 50 and starting to think seriously about protecting your nest egg, this is one episode you won’t want to miss.

Here’s some of what we discuss in this episode:

🌪️ Why...

The market’s hitting record highs, but does that mean it’s too risky to invest right now? In this episode, Scott breaks down what all-time highs actually mean for long-term investors. You’ll hear how short-term fear often leads to poor decisions and why zooming out can help you stay grounded.

Here’s some of what we discuss in this episode:

📈 Why investing at all-time highs isn’t as scary as it seems

⏳ Why time in the market beats tim...

Dave Ramsey is one of the most recognized voices in personal finance. His 9-step retirement plan is simple, direct, and built for mass appeal. But is it really the best path for your retirement? 

You'll hear where Scott agrees, where he diverges, and what every pilot needs to know about balancing tax strategies, health care costs, and when to bring in an advisor. 

Here’s some of what we discuss in this episode:

🚨 What ...

The Big Beautiful Bill (BBB) is here, and with it comes tax updates that could shape your financial strategy for years to come. In this episode, Scott and Marc break it all down in clear, practical terms: what stays, what changes, and what it means for pilots, high earners, and retirees alike. But here’s the catch: many of these changes are temporary, so smart planning now could make a big difference later.

Here’s some of what we di...

As we celebrate the Fourth of July, this episode explores what independence truly looks like in retirement, beyond fireworks and freedom. Scott dives into five core areas of independence that every retiree (or future retiree) should be aiming for as they prepare for life after work. It's not just about having enough money, but having control, peace of mind, and a plan that works.

Here’s some of what we discuss in this episode:

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Estate planning is something we all know we should do, but it’s often pushed to the bottom of the list. In this episode, Scott shares a heartbreaking real-life story: a close friend’s brother died suddenly at 42. Recently divorced, with two young sons and no estate plan in place, the aftermath was a painful legal tangle. It’s a tragic example of what happens when planning is left undone, and how the people you love end up bearing t...

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision?

Here’s some of what we discuss in this episode:

📏 Why the 4% rule became the “default” retirement plannin...

Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? 

Here’s some of what we discuss in this episode:

🧭 Why defaulting to a target-date fund could misalign with your goals

📉 How these funds reduce risk—but possibly too early or too much

⚠️ The hi...

A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Scott’s walking through five common examples of wishful thinking that can quietly damage your retirement, and how you can build a plan that protects your future instead of relying on luck.

Here’s some of what we discuss in this episode:

🧾 A major tax myth you need to face

🏠 Does cost of living...

Today, we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented, then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. 

In this episode, Scott breaks down the challenges Type A investors face when market volatility strikes and why a hig...

We’ve all heard that Americans don’t save enough for retirement, but what if the opposite is true for you? Can you save too much? In this episode, Scott tackles a surprising but important question raised by a listener: “Are we over-saving at the expense of living now?” As an airline professional, it can be easy to feel like you’re doing too little, or maybe even too much. This conversation helps you find the balance.

Here’s some of ...

Recession fears are back in the headlines, but should they be back in your financial plan, too? We’re in the middle of earnings season and data is coming in, so Scott will tackle the question: Are we heading for a recession? 

With shrinking GDP, rising inflation, and uncertain interest rate moves by the Fed, we’ll try to decipher what the latest economic signals really mean and discuss how investors should think about their portfoli...

In part two of this special Masters series, Scott takes us to the “back nine”- the final stretch of retirement planning where pressure builds and smart decisions matter most. From avoiding risky plays in your 50s and 60s to understanding how emotions can derail your strategy, Scott lays out what it really means to finish strong.

Here’s some of what we discuss in this episode:

⛳ Why “Amen Corner” = age 50+ in your financial life

🎯 Avo...

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, we’re teeing up a few key lessons from the course and how they translate into smarter planning for your financial future.

Here’s some of what we discuss in this episode:

⛳ What golf teaches us about investing

⚠️ Avoiding overconfidence after short-term win...

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy amidst federal layoffs and tariffs. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it?

Here’s some of what we discuss in this episode:

0:00 – Intro

2:08 – Headline response to market

3:49 – Sequence of returns risk

6:19 – Different market sector...

What if you could become your own banker and take control of the way you finance your life? Today we’re excited to welcome on Brian Moody and Hans Tooey of Remnant Finance to explore the Infinite Banking Concept- a financial strategy designed to help you protect, save, and grow your wealth without relying on traditional banks.

Here’s some of what we discuss in this episode:

0:00 – Intro

1:00 – Background on our guests

4:50 – The Infini...