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

Be a Coffee Bean: A Story of Resilience & Redemption with Damon West 16.09.2023

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 today, the best-selling author and motivational speaker Damon West. His story of transformation is unlike any other, filled with tales of resilience, hope, and a unique perspective on life that only prison walls could provide. He went from bein...

Brick and Mortar Retirement: The Pros and Cons of Real Estate Investing for Retirement 17.08.2023

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 mortgages. Whether you're a pre-retiree with a portfolio of properties or just curious about leveraging your home equity, this discussion offers thoughtful insights for anyone navigating the crossroads of real estate and retirement.   Home...

Retirement: Ready Or Not, Here It Comes 04.08.2023

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 intricacies of this decision, addressing both financial and emotional aspects, and help you find out if you’re truly ready to retire.   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilo...

Coaches For Charity Event with Legendary Football Coach Fisher DeBerry 13.07.2023

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 learn about their mission. You can also learn more online at https://southcarolinacoaches.com and if you're nearby, consider attending the annual gala on Monday, July 17, 2023.   Show Notes & Info: Retire Pilots Website - https://retire...

Fore Your Retirement: What Golf Teaches Us About Financial Planning 06.07.2023

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 thrilling, but it won't necessarily guarantee your overall success. And just like you need different clubs in your golf bag to play a round, you need a well-balanced approach to your investments in retirement. But perhaps the most important les...

Enhance Your Retirement Planning with IBC 15.06.2023

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 retirement planning by eliminating the risk associated with a sequence of returns and offering a volatility buffer. Learn how borrowing tax-free income from the insurance policy can protect your retirement portfolio during market downturns, the...

The Infinite Banking Concept: A More Flexible Approach To College Savings 01.06.2023

Today we are back with David Befort, the CEO of Max Performance Financial. We find that many of our clients are using 529 plans to prepare for their children's future, but is this the best option? In this episode, we'll highlight the limitations of 529 college savings plans and the potential issues pilots face when using them. We'll then discuss some advantages of IBC, or the infinite banking conc...

The Secret Banks Don’t Want Pilots To Know: How To Create YOUR OWN Banking System 18.05.2023

David Befort joins us on today's show. David is the CEO of Max Performance Financial where his mission is to help his clients control their own money. We will be discussing what strategies David uses in his practice and why these can potentially give you more freedom than a typical banking system.   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://r...

Should An Advisor Tailor A Plan To Fit Your Personality? 04.05.2023

Are you tired of one-size-fits-all financial advice that doesn't quite fit your unique needs and goals? In this episode, we'll tackle the question of whether an advisor should tailor a plan to fit your personality. We'll discuss the pros and cons of different approaches and explore how understanding your financial personality can help you make more informed decisions. Show Notes & Info: Retire Pil...

Retirement Expenses For Which You Forgot To Plan 20.04.2023

Are you preparing for retirement but feeling confident that you have covered all the expenses? Well, think again… It turns out that many retirees overlook some crucial expenses that can leave them financially vulnerable. In this episode, we explore the retirement expenses that most people tend to forget, including skyrocketing medical bills, unexpected travel costs, taxes, and much more. We'll dis...

Should I Pay Off The House? 06.04.2023

For many people, their house is the largest asset they own. Many people wonder if they should pay off their house before they go into retirement, or if it's okay to still carry a mortgage in this phase of life. Ryan will give us some considerations when making this important decision and some common situations he sees with his clients. Show Notes & Info: Home Equity PDF: https://bit.ly/42PZJo2 Ret...

Pilot Tax Tips: Moves To Make for 2023 and Beyond 16.03.2023

It’s tax season once again and that means Zach Smith of Pilot Tax is back for another episode to help break down some of the tax moves we should be considering for this year and beyond. Join Zach and Ryan as they analyze what future tax rates might look like, how the Secure Act 2.0 legislation could impact your bottom line, and whether it’s wise to over fund a 529 plan. Show Notes & Info: Retire P...

Moving Your Retirement Goalposts: Is It Worth The Risk? 09.03.2023

Do you ever feel like your retirement planning goals are always moving? You're not alone. We’ve found that people often move the goalposts in their own retirement planning, often to their detriment. In this episode, we're diving deep into the psychology of retirement planning and the dangers of moving the goalposts. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement To...

What’s Your Biggest Financial Fear? 16.02.2023

We took an informal poll of listeners to find out what their biggest financial fears are. On this episode, we’ll explore the most common fears and talk about how they should be addressed in a retirement plan. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Four Ways The SECURE Act 2.0 Might Impact You 02.02.2023

After being discussed in Congress for nearly a year and a half, the SECURE Act 2.0 passed in January. Listen to today’s episode to see what you need to know and learn four ways the new changes might impact you. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

2023 Edition: 10 Point Checklist For Retirement Preparedness 19.01.2023

Another year is upon us and it’s a great time to ask yourself 10 questions to assess how ready you are for retirement to kick off 2023. If you’re retiring this year, it’s essential to have some concrete answers to these questions. If you’re still a few years from the milestone, tune in so you can start thinking about these critical conversations. In a non-financial topic, Ryan shares his thoughts...

New Year Musings: What Financial ”Stuff” Should Capture Your Attention In 2023 10.01.2023

As we turn the page to a new year, Ryan looks back at lessons learned from 2022 and analyzes predictions for what 2023 will bring. We'll touch on taxes, inflation, the stock market and topics specific to the airline industry. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Level Up Your Financial Knowledge: Stock Market Topics To Know 15.12.2022

If you’ve ever wanted to just learn a little more about investing in the stock market, this episode is for you. We’re going to cover some of those terms you’ve probably heard before, but perhaps never truly knew what they meant. Show Notes & Info: Webinar link https://retirepilots.com/2022/11/how-to-survive-a-bear-attack/?inf_contact_key=374777225ed5fcfe65812a763a9df2cf Link to NASDAQ, DOW and S&P...

Is There Greener Grass On The Other Side? 01.12.2022

Sometimes you need to find a new financial advisor. Other times, you might think you need a new advisor, but really, you’re just guilty of thinking that the grass is greener on the other side. Let’s discuss some common scenarios and whether they’re legitimate reasons for leaving your advisor… Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepi...

The Retirement Marathon: Finishing The Race 17.11.2022

Getting through retirement can be a lot like running a marathon. Let’s talk about some of the similarities between getting to the finish line in racing and retirement. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

How Money Ads Catch Your Attention 03.11.2022

We’re bombarded with ads each day in all forms of media. But have you ever taken a closer look at these messages? If we unpack some of these headlines and ads a little bit more, we’re able to clearly understand what emotions they’re trying to elicit. More importantly, we can figure out what companies are trying to sell us. For this episode, we just perused the internet for a couple of hours and ke...

Retirement Planning From A Psychologist’s Point Of View 20.10.2022

We always talk about the money side of financial and retirement planning. But what about the mental aspect of that big life change? Today we’ll break down an article written by a Licensed Professional Counselor (Kate Schroeder) for Psychology Today, titled The Psychological Investment In Retirement. Link to article : https://bit.ly/3SfMNBG Show Notes & Info: Retire Pilots Website - https://retirep...

Tough Topic: Retirement & Divorce 30.09.2022

Going through a divorce at any age is difficult, but doing it near or in retirement adds all sorts of additional complications. On this episode, we’ll talk about some of the financial mistakes we see people make in the midst of a divorce. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/

Advice If You Feel Panic About The Current Stock Market & Economy 22.09.2022

Are you feeling worried or experiencing any sense of panic as you watch the stock market go up and (mostly) down these days? Does the state of the economy add to your personal stress? These could all be signs you don't have a great financial plan in place that's built to weather the kinds of storms we're in at this moment. On this episode, Ryan shares a helpful perspective aimed to limit any anxie...

Can You Get An A+ On Our Retirement Planning Quiz? 15.09.2022

Don’t dread this as much as you hated hearing these words as a kid, but it’s time for a pop quiz! We’re putting retirement planning preparedness under the microscope with 5 critical questions to which you need to know the answers. So sharpen those pencils and let’s see how ready you are for retirement. Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https:...

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