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

Why Retirement Planning Ain’t What It Used To Be 01.09.2022

In some ways, retirement planning was easier for past generations. Let’s explore how a good financial advisor helps people overcome the additional challenges of today. Our parents and grandparents may not have had to face these things, so just relying on the experiences of family members might not be enough to help us achieve our own financial success… Show Notes & Info: Retire Pilots Website - ht...

Are You A Risk Taker? How To See If Your Tolerance For Risk Matches Your Plan And What To Do If The Balance Is Out Of Whack 18.08.2022

Let’s see if your tolerance for risk matches your financial plan. What should you do if that balance is out of whack? What if you’re a natural risk taker, but you really shouldn’t be when it comes to your finances? We’ll explore all of these angles as we break down the role of risk in your financial and retirement plan. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retiremen...

Market Update From A Cruise 05.08.2022

We have a bit of a different show for you today. Ryan is currently on a cruise in the Mediterranean and Walter is on a beach in South Carolina, but they carved out some time to provide an update on what's going on in the market. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Do You Concur? Picking Sides In Important Financial Debates 04.08.2022

On this episode, we’ll try to pick sides of some important financial debates. From bonds to life insurance, credit card debt to starting Social Security, we’ll propose several different topics to see which sides of the debates you and your advisor should probably fall on.  Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/...

Investor Beware: Spotting Red Flags When Picking An Advisor 21.07.2022

Do you know what red flags, but also some good signs, to be on the lookout for when you’re searching for an advisor to work with as you prepare for retirement? On this episode, we’ll give you some red flags to be aware of, teach you how to spot them and illustrate the difference between an advisor who does the bare minimum versus one who goes above and beyond to work in your best interests. Show N...

Bear Market Council 14.07.2022

On this episode, Ryan will discuss the bear market we have been experiencing this year and why now is not the time to panic. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Two Cow 07.07.2022

Ryan brings on a special guest, Jesse "Two Cow" Barnes, to swap some flight stories and to share Two Cow's weight loss journey. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/ Two Cow on Instagram - https://www.instagram.com/fatsalmon123/

A Random Walk Down Wall Street With Lee Hyder 30.06.2022

Times are turbulent in the market right now and many people feel panicked about their portfolios. We bring on Lee Hyder to discuss why volatile times are not as big of a deal as they seem and the importance of thinking logically in these rough patches. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://p...

Keeping Perspective In A Bear Market 14.06.2022

Ryan breaks down the recent downturn in the stock market to look historically at bear markets, when they lead to recessions, and how to digest all of this as it relates to your own financial plan. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Should Investing Be Boring? 19.05.2022

Let's face it. Nobody wants to be boring. We all want a little excitement in our lives. But what about when it comes to investing? In this episode, Ryan ponders if this is the one area where it's OK to be bored. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Market Timing: Is It A Legitimate Strategy For Pilots To Build Wealth? 12.05.2022

The prospect of timing the market is so tempting. But so many people forget that you have to be right twice to do it properly. And being right twice is harder to accomplish than you think. On this episode, Ryan takes a hard look at timing the stock market to analyze whether it's a legitimate strategy for pilots to build wealth. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ R...

The Retirement Diet: Fixing Unhealthy Financial Habits 05.05.2022

We all know some of the basic secrets of eating healthier to lose weight, limit disease, and live longer. Avoid empty calories, try to limit your added sugar, and lower those pesky trans fats are just some examples. But how can we spot similar unhealthy habits in the financial world? We’ll talk about it on this episode and help you fix some of your unhealthy financial habits. Show Notes & Info: Re...

Common Housing Questions From Retirees 21.04.2022

Housing is a really important topic for a lot of retirees because, for many of us, it’s the biggest asset we’ll ever own or manage. We want to get that part of our financial equation correct, so it’s no surprise it takes up a nice slice of the retirement planning conversation. On this episode, we’ll cover some common housing questions from retirees and hopefully hit on an issue that might also be...

Reasons You SHOULD Get Life Insurance 07.04.2022

Sure, life insurance is one of the more boring topics to cover on a podcast. And a lot of what you hear is going to warn you why you should NOT get various types of life insurance. But our goal on this episode is to focus on the positive and analyze the reasons why you should get life insurance, or at least consider it. Many people think that once the kids are out of the house, you don’t need insu...

Article Breakdown: Murky Issues That Make Retirement Planning Harder 31.03.2022

This USA Today article points out 3 murky issues that increase retirement planning’s degree of difficulty, especially in today’s economic climate. On this episode, we’ll breakdown the article to see if it’s worthwhile advice, if the murky issues are actually that threatening, and what you can do about all of it if you’re concerned. Show Notes & Info: USA Today Article: https://bit.ly/3tdWyqs Retir...

What They’re Saying: What Is The Most Important Part Of Retirement Planning? 17.03.2022

We all should realize that planning for retirement is relatively complex. There are a lot of different moving parts and factors to consider. Adjusting any of these variables can impact the end result. But is there one part of the retirement planning process that’s most important? We’ve assembled several opinions on the topic from across the internet. Let’s see if the advice hits the mark or needs...

Who Even Needs A Financial Advisor? 17.02.2022

Some people feel that they’ll save money by handling their investments themselves instead of working with an advisor. Others may like the challenge of doing it themselves. Still others just don’t know who to trust so they end up not working with anyone. Let’s talk about some reasons that you might need an advisor… Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Tool...

Here We Go Again... More 1st Quarter Turbulence 03.02.2022

We've been here before. For the third straight year, the first quarter of the year is seeing all sorts of market turbulence. We'll catch up with Ryan to find out how he's helping clients navigate through the market volatility, dealing with inflation, and what else he has his eye on in 2022. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://3mvamj4f.p...

Where Financial Advisors Drop The Ball 20.01.2022

We see a lot of people who aren’t getting the kind of advice and service from their financial advisor that they should be. In a lot of cases, the advisor is only “managing the investments,” but not providing guidance in other areas. Let’s talk about some of the things that your advisor should be doing… Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.fle...

Retirement Is As Easy As A Jigsaw Puzzle 02.12.2021

To successfully complete a jigsaw puzzle, there are some strategies that you’ll want to keep in mind. And many of those same strategies apply to retirement planning. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

Handling Unreasonable Requests 18.11.2021

Certainly, none of our podcast listeners would be guilty of making unreasonable requests, but let’s talk about some of the unreasonable requests we hear from others in the financial world. We’ll explore what makes them unreasonable and what proper expectations look like instead. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3...

Living The Dream & ”Noodling” Around In Retirement 04.11.2021

Before you can live the retirement dream, you have to figure out what the dream looks like in the first place. Let’s talk about some of the things you need to dream about… Walter will also teach Ryan about the joys of "noodling around" when on vacation. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft...

Analyzing Dave Ramsey‘s Advice 21.10.2021

Ryan and Walter discuss a recent article that says listeners of Dave Ramsey should disregard some of his tips and tricks. The two look at each point and Ryan offer his insight into what tips he believes may or may not be beneficial. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

Answering Questions From Listeners 07.10.2021

Ryan answers questions submitted by listeners on an assortment of financial planning topics. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

Spotting Red Flags In Your Finances 16.09.2021

Depending on your answers, the questions we cover on today’s show might raise red flags about your finances… Also, Ryan shares with us a big change in his life. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

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