Shows / The Pilot’s Advisor Podcast
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
- The Pilot’s Advisor Podcast
Mailbag: Trading Options? Think Again, Captain
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Today’s story is all too familiar: a pilot…
- The Pilot’s Advisor Podcast
No Empty Nest in Sight? How Pilots Can Still Land a Smooth Retirement
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Raising kids used to follow a predictable…
- The Pilot’s Advisor Podcast
Mailbag: Should You Sell Inherited Land to Pay Off Your Mortgage?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ In this episode, Ryan answers a thoughtful…
- The Pilot’s Advisor Podcast
The 4% Rule Just Changed—What That Means for Your Flight Plan to Retirement
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…
- The Pilot’s Advisor Podcast
War, Rates & Real Estate—Plus Smart Money Moves for New Grads
In this episode, Ryan delivers a “pilot report,” offering a timely look at today’s economic turbulence. From global conflict and rising interest rates to…
- The Pilot’s Advisor Podcast
A Market Strategy for Pilots With Type A Personalities
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…
- The Pilot’s Advisor Podcast
Why The Psychology of Money Says Your Emotions Matter More Than Math
Today, Ryan’s taking us through some of the key concepts of The Psychology of Money by Morgan Housel. This book isn’t just about money strategies. It’s about…
- The Pilot’s Advisor Podcast
Is It Bad to Leave My 401(k) Where It Is?
If you've recently changed jobs, chances are your old 401(k) is still sitting right where you left it – out of sight and out of mind – and it could potentially…
- The Pilot’s Advisor Podcast
Mailbag: Market Crashes, Corrections, and Staying Calm
The market’s been shaky and pilots are wondering how the volatility impacts their retirement and investment decisions. In this special mailbag edition of the…
- The Pilot’s Advisor Podcast
Spring Cleaning for Your Finances: A Marie Kondo Approach to Money
Spring is in the air and for some, that means it’s time for spring cleaning. Marie Kondo is considered an expert in tidying and decluttering, and wrote the…
- The Pilot’s Advisor Podcast
I Went to the New York Stock Exchange - Here’s What I Learned
Ryan just got back from the New York Stock Exchange, and he’s sharing what it was like to stand on the floor during the iconic closing bell. Go behind the…
- The Pilot’s Advisor Podcast
What the Greats Say About Market Crashes
When the market is crashing, it's easy to feel like you're the only one who's ever felt this anxious. But the truth is, some of the greatest investors in…
- 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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- 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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
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…
- The Pilot’s Advisor Podcast
Planning Essentials for Pilots Nearing Retirement
This is a special edition of the Pilots Advisor podcast with Ryan Fleming. He had a recent guest appearance on the Wealth Warehouse…
- The Pilot’s Advisor Podcast
Mailbag: Should I Fly Until Age 65?
As a pilot, you've spent countless hours navigating the skies, managing complex flight systems, and ensuring the safety of your passengers. But when it comes…
- The Pilot’s Advisor Podcast
Never Stop Asking 'How Do You Know?' - Helping Pilots Navigate Retirement Planning
As a pilot, you've spent years mastering the complexities of flight. But when it comes to planning for retirement, do you find yourself asking, "How do I…
- The Pilot’s Advisor Podcast
Infinite Banking & Other Pilot Strategies with the Wealth Warehouse
Today we have a special edition of the show where we’re going to share Ryan’s recent appearance on the Wealth Warehouse show with David Befort and Paul Fugere…
- The Pilot’s Advisor Podcast
Should you invest through Howard Capital Management?
Pilots are always looking for investing strategies that can help them grow their money and we’ve introduced quite a few people to Howard Capital Management…
- The Pilot’s Advisor Podcast
Deep Thoughts on the Market & Investing with Lee Hyder
As we move past Memorial Day and into the summer, we’re excited to welcome back Lee Hyder of Lee Hyder & Associates today to reflect on where the market…
- The Pilot’s Advisor Podcast
Mastering the Art of Simple Retirement Planning for Airline Pilots
Retirement planning doesn’t have to be overwhelmingly complicated. In fact, it doesn’t have to be as complicated as most people tend to make it. In this…
- The Pilot’s Advisor Podcast
Expectation vs. Reality: The Truth About Retirement Planning
Some people just need a reality check when it comes to understanding their retirement. Today, we'll explore why a realistic approach to retirement, inclusive…
- The Pilot’s Advisor Podcast
Retirement Planning Is Harder Than It Used To Be
Every generation likes to talk about how much harder things used to be when they were kids. Like all of the people who used to have to walk five miles to…
- The Pilot’s Advisor Podcast
Don’t Make These Income Planning Mistakes
Are you planning for your retirement with the confidence that you're making all the right moves? In today's episode, we'll unveil the crucial income planning…
- The Pilot’s Advisor Podcast
What Leads to Investing Mistakes?
Being a better investor doesn’t require you to spend hours and hours researching the latest trends and market data. The most important change people can make…
- The Pilot’s Advisor Podcast
Reflecting on a College Football Career & Retirement with Larry Fedora
Today we’re going to catch up with Coach Fedora to reflect on a successful career in the sport. We want to hear some of his best stories about Air Force and…
- The Pilot’s Advisor Podcast
What should I do with my Delta profit sharing bonus?
Delta paid out a large profit-sharing bonus this month, which is great for those pilots who received a check on Valentine’s Day. The question we get a lot when…
- The Pilot’s Advisor Podcast
Crafting Investment Philosophies Around Retirement with Lee Hyder
We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to share insights and stories from 30+ years of experience. Join us as we go back and forth…
- The Pilot’s Advisor Podcast
Will The Economy Boom Or Bust In 2024?
Everyone wants to know. Will the economy boom or bust in 2024? Join us as we explore a range of expert predictions, from the shifting trends in housing prices…
- The Pilot’s Advisor Podcast
Soaring Above Market Turbulence with Lee Hyder
We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to share insights and stories from 30+ years of experience. Join us as we go back and forth…
- The Pilot’s Advisor Podcast
Breaking Down the Details & Financial Impact of the New Southwest Airlines TA
This episode is going to delve into the significant new Tentative Agreement for Southwest Airlines pilots and break it all down so you know the most important…
- The Pilot’s Advisor Podcast
The Power of Delayed Gratification
Sometimes it’s hard to make financial sacrifices when the reward might not be seen until several years in the future, but the idea of delayed gratification is…
- The Pilot’s Advisor Podcast
Should You Take the new Delta GVUL Option?
The goal for the show today is to provide you with a broad picture of being offered and share some things from our research that Delta pilots should be aware…
- The Pilot’s Advisor Podcast
Never Lose the Power of Your Money with Dave Befort
The idea we’ve been exposed to about investing is that our money can only be in one place at a time, right? That’s all we’ve ever heard, but that’s not exactly…
- The Pilot’s Advisor Podcast
Rethinking Your Survivor Benefit Options with Dave Befort
Many of the FedEx and UPS pilots still have a pension and they often ask what to do about the survivor benefits. Many of them are inclined to lean towards the…
- The Pilot’s Advisor Podcast
Recapping the 2023 South Carolina Coaches for Charity Event with Steve Sharp
We’ve talked about it some already on the show, but the South Carolina Coaches for Charity event has become a passion of ours. The money raised goes to help…
- The Pilot’s Advisor Podcast
Be a Coffee Bean: A Story of Resilience & Redemption with Damon West
Imagine being addicted to meth and leading an organized crime ring, only to be arrested and sentenced to life in prison. That was the reality for our guest…
- The Pilot’s Advisor Podcast
Brick and Mortar Retirement: The Pros and Cons of Real Estate Investing for Retirement
In this episode, we construct a helpful conversation about the role of real estate in a retirement strategy, exploring everything from rental income to reverse…
- The Pilot’s Advisor Podcast
Retirement: Ready Or Not, Here It Comes
Are you nearing “retirement age”? If so, let’s explore that pivotal question you’ll soon face: Should you retire or continue working? We’ll unravel the…
- The Pilot’s Advisor Podcast
Coaches For Charity Event with Legendary Football Coach Fisher DeBerry
Legendary football coach Fisher DeBerry joins Ryan to discuss the South Carolina Coaches for Charity Event. This year might be the biggest event yet. Listen to…
- The Pilot’s Advisor Podcast
Fore Your Retirement: What Golf Teaches Us About Financial Planning
Are you a golfer? Even if you're not, the game of golf can teach us valuable lessons about retirement planning. For example, hitting a hole-in-one might be…
- The Pilot’s Advisor Podcast
Enhance Your Retirement Planning with IBC
Today we are joined by Dave Befort, CEO of Max Performance Financial and IBC practitioner. In this episode, Dave will explain how utilizing IBC can enhance…