Ryan Fleming

The Pilot’s Advisor Podcast

Business EN ↓ 219 episodes

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.

Author

Ryan Fleming

Category

Business

Podcast website

pilotsadvisor.podbean.com

Latest episode

Jul 7, 2026

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Episodes

Market Volatility: When Should You Start To Worry? 21.11.2024

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 fa...

How The Fed Rate Cut Impacts Money Market Funds 14.11.2024

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....

Can You Live Off Dividends? 07.11.2024

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...

Planning Essentials for Pilots Nearing Retirement 31.10.2024

This ​is ​a ​special ​edition ​of ​the ​Pilots ​Advisor ​podcast ​with ​Ryan ​Fleming. ​He ​had ​a ​recent ​guest ​appearance ​on ​the ​Wealth ​Warehouse ​podcast ​where ​Ryan ​shared ​essential ​insights ​for ​pilots ​nearing ​retirement ​or ​planning ​for ​the ​future. ​ In ​the ​episode, ​he ​breaks ​down ​effective ​strategies ​for ​building ​stability ​through ​tools ​like ​dividend-paying ​w...

Mailbag: Should I Fly Until Age 65? 12.09.2024

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 to navigating your retirement, there’s often more questions than answers. In this episode, Ryan answers a critical question from a listener about flying until 65 or whether there is flexibility to retire earlier?   Here’s what we cover in thi...

Never Stop Asking 'How Do You Know?' - Helping Pilots Navigate Retirement Planning 29.08.2024

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 know?" Understanding the right questions to ask and finding the answers is crucial for securing your financial future. In this episode, we dive deep into the essential retirement planning questions every pilot should be asking.   Here’s what we c...

Infinite Banking & Other Pilot Strategies with the Wealth Warehouse 18.07.2024

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. David is the Founder/CEO of Max Performance Financial. He founded the company with the mission of educating people on the truths about money. Paul, on the other hand, is an Active Duty U.S. Army officer who graduated from Norwich University...

Should you invest through Howard Capital Management? 11.07.2024

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. Today we are going to share our experience with their investments and why it might be worth considering if you want something a little different than the traditional funds.     Here’s what we cover in this episode: 0:00 – Intro 1:35 – Howard C...

Deep Thoughts on the Market & Investing with Lee Hyder 20.06.2024

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 currently stands and the investing strategies pilots should be focused on for long-term success. We always appreciate the perspective Lee brings to the show and wanted to get his deep thoughts on a few different topics. During this episode, he...

Mastering the Art of Simple Retirement Planning for Airline Pilots 06.06.2024

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 episode, we’re going to unravel some of the unnecessary complexities that are often woven into the fabric of retirement advice. Ryan will debunk some of the myths, simplify some strategies for us, and uncover the beauty of simplicity and straightf...

Expectation vs. Reality: The Truth About Retirement Planning 16.05.2024

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 of financial planning and the potential for unexpected challenges, is crucial. We’ll take a look at four different examples of times when expectations don’t match up with reality for pilots, and Ryan will share his expertise to help you get a...

Retirement Planning Is Harder Than It Used To Be 02.05.2024

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 school, in the snow, uphill both ways. But they had at least one thing that was EASIER…and that was retirement planning.   Here’s what we cover in this episode: 0:00 – Intro 2:21 – Change from generation to generation 3:30 – Company loyalty 4:51...

Don’t Make These Income Planning Mistakes 18.04.2024

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 mistakes that could jeopardize your retirement. Tune in to ensure your retirement strategy is foolproof against common pitfalls and ready to secure your financial future.   Here’s what we cover in this episode:   0:00 – Intro 4:38 – Planning...

What Leads to Investing Mistakes? 04.04.2024

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 is taking emotions out of their decision-making. It’s much easier said than done, which is why we see people make these same emotional mistakes time and time again.   We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to...

Reflecting on a College Football Career & Retirement with Larry Fedora 07.03.2024

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 other stops, but we’ll also talk about life off the field as well. From a social media picture that went viral to a weightlifting scare, this show will cover a lot of ground with someone we respect highly. Plus, we’ll get his opinion on the st...

What should I do with my Delta profit sharing bonus? 22.02.2024

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 these bonuses get paid is what should you be doing with it? We wanted to shoot this short video to provide some general guidance for pilots who have some extra money to invest or save. It might not be specific advice but it should give you...

Crafting Investment Philosophies Around Retirement with Lee Hyder 12.02.2024

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 on the highs and lows investors face, underscoring the need for resilience and a long-term outlook when building a portfolio for retirement. We spend the first part of the how discussing fees and how you should approach them with your i...

Will The Economy Boom Or Bust In 2024? 01.02.2024

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 to the looming question of a potential recession or stock market crash. We'll balance our discussion with both optimistic and pessimistic perspectives from an array of sources to give you a comprehensive view. Ryan will also weigh in with hi...

Soaring Above Market Turbulence with Lee Hyder 25.01.2024

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 on the highs and lows investors face, underscoring the need for resilience and a long-term outlook.   Here’s some of what we discuss in this episode: 0:00 – Intro 2:41 – Keeping up with change in the industry 4:07 – Using technology to...

Breaking Down the Details & Financial Impact of the New Southwest Airlines TA 17.01.2024

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 details. By the end of the show, you should be up-to-date on the impact and the implications of the TA. We’ve invited Captain Robert Ecklund of Southwest Airlines to talk about some of the key aspects of the contract that's coming out, inclu...

The Power of Delayed Gratification 08.01.2024

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 at the core of retirement planning. In this episode we’ll talk about some of the situations where you might be inclined to take the immediate benefit when you should really consider the delayed rewards.    Here’s some of what we discuss in t...

Should You Take the new Delta GVUL Option? 30.10.2023

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 of and think through. Plus, we’ll offer some alternative options to this GVUL policy for pilots looking for a safe asset. If you’re just looking for a quick cliff notes version of what we discuss, skip to the final few minutes to hear us summ...

Never Lose the Power of Your Money with Dave Befort 12.10.2023

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 true. Your money can work for you in two different places thanks to the Infinite Banking Concept. It’s a strategy that we’ve previously discussed with today’s guest, Dave Befort , but today we want to dive into how to truly harness the powe...

Rethinking Your Survivor Benefit Options with Dave Befort 28.09.2023

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 50% survivor benefit, but that’s not typically the best option. To help us explore some of these other options, we’ve invited Dave Befort onto the podcast today. He’s an expert in the Infinite Banking Concept for pilots as well as many other...

Recapping the 2023 South Carolina Coaches for Charity Event with Steve Sharp 21.09.2023

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 some outstanding charities, including the Fisher DeBerry Foundation started by Ryan’s former head coach. Our goal for the 2023 event was to pour our time and effort into helping the organizers continue to grow the event and build on the succes...

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