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
How Do Pilots Know When It's "Safe" to Retire?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ "When can I retire?" might be the question…
- The Pilot’s Advisor Podcast
A New Bill Would Lower the Social Security Retirement Age… For Some
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ A new bill in Congress would let some…
- The Pilot’s Advisor Podcast
Adapting to Change Without Losing Your Cool
What if the biggest step forward is letting go of what you can’t control? In this episode, Ryan reflects on personal growth, staying grounded amid uncertainty…
- The Pilot’s Advisor Podcast
Conversation Starters: Questions Pilots Should Ask To Reveal Financial Truths
Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he…
- The Pilot’s Advisor Podcast
Inflation, Purchasing Power & the Risk of Being Too Conservative
Inflation doesn't arrive as a bill in the mail, but over time it can quietly take a serious bite out of your purchasing power. Ryan uses a humorous quote about…
- The Pilot’s Advisor Podcast
The Pilot Retirement Reality Check: 2026 Version
Retirement planning today doesn't look like it did even a decade ago, let alone the way it looked for our parents. On this episode, Ryan provides several…
- The Pilot’s Advisor Podcast
Rejection, Career Detours &… A Secret Crush!?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Ever had a job that humbled you, but quietly…
- The Pilot’s Advisor Podcast
Why People Keep Working In Their Retirement Years
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ More people in their 60s and 70s are staying…
- The Pilot’s Advisor Podcast
Cell Phones Changed More Than Communication
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ What started as a nostalgic conversation…
- The Pilot’s Advisor Podcast
What Happens When Pilots DIY Their Retirement Plan
There's an entire television network dedicated to doing things yourself — home renovation, landscaping, interior design, all of it. And the DIY mentality is…
- The Pilot’s Advisor Podcast
FedEx Pilots: Don’t Spend That Lump Sum Until You Hear This
FedEx pilots are about to receive a significant lump sum, and what happens next could have a lasting impact on their financial future. In this episode, Ryan is…
- The Pilot’s Advisor Podcast
Is Your Advisor Talking Over Your Head?
Ever felt like your advisor is speaking a different language? Ryan unpacks what to do when financial jargon gets in the way of understanding your money. He…
- The Pilot’s Advisor Podcast
How Much Money Is Too Much in the Bank?
Ever wonder if your “safe” cash is actually holding you back? In this episode, Ryan answers a listener’s question from a pilot who has built up $150,000 in…
- The Pilot’s Advisor Podcast
Dave Ramsey Says You Can Withdraw 8% - Here's What the Research Actually Says
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Dave Ramsey has built one of the most…
- The Pilot’s Advisor Podcast
Trump Accounts: Free Money or Financial Distraction?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Trump Accounts are here, but are they really…
- The Pilot’s Advisor Podcast
What Your 4th of July Traditions Can Teach You About Money
This year's Fourth of July carries a little extra weight as we celebrate 250 years of American independence, and that's worth a moment. But between the hot…
- The Pilot’s Advisor Podcast
SDBAs vs. Target Date Funds – The 401K Mistake Most Pilots Make
If you're a pilot, there's a good chance your retirement savings are sitting in a target date fund you selected years ago and haven't thought about since. The…
- The Pilot’s Advisor Podcast
In Your 50s & 60s? Here's What "Risk" Should Look Like Right Now
Many pilots assume that as retirement gets closer, they should automatically become more conservative with their investments. But according to Ryan, that's not…
- The Pilot’s Advisor Podcast
What Does Smart Risk Actually Look Like in Your 30s & 40s?
Risk is unavoidable. The real question is whether the risk you're taking makes sense for where you are in life. In this episode, Ryan explores three common…
- The Pilot’s Advisor Podcast
Maverick, Goose, and the Financial Danger Zone
It's summer and nothing says summer quite like Tom Cruise as Maverick soaring across the sky in Top Gun. This year marks the 40th anniversary of the original…
- The Pilot’s Advisor Podcast
FedEx Pilots’ Guide to TA 2026: The Smart Tax Moves
In this episode, Ryan is joined once again by CPA Zach Smith to unpack the FedEx TA 26 retirement choices, this time from a tax and long‑term planning angle…
- The Pilot’s Advisor Podcast
FedEx TA 2026: 3 Retirement Options That Could Change Everything
USE THIS: FedEx TA26 Retirement Option Tool. Check out our educational modeler - https://retirepilots.com/fedex-ta26-tool/ FedEx pilots are facing a major…
- The Pilot’s Advisor Podcast
What Pilots Are Googling About AI & Retirement
AI isn’t just a buzzword, it’s quickly becoming one of the biggest unknowns in retirement planning. Pilots in their 50s and 60s are actively searching for…
- The Pilot’s Advisor Podcast
Will AI Replace Pilots in the Next 5 Years?
AI is changing everything right now, and aviation isn’t going to be immune to that. The question is… what does it actually mean for you as a pilot? Ryan breaks…
- The Pilot’s Advisor Podcast
Life Insurance For Pilots: Term, Whole, or Universal Life?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ We got a great question from a listener…
- The Pilot’s Advisor Podcast
War with Iran, Energy Prices, and Your Money: What You Need to Know
When global conflict makes headlines, it’s natural to wonder what it means for your money. In this episode, Ryan breaks down how markets are reacting to the…
- The Pilot’s Advisor Podcast
Tax Mistakes New Retirees Make
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Nobody likes tax season, but for new…
- The Pilot’s Advisor Podcast
And the Oscar Goes To... Your Retirement Strategy
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ The Oscars celebrate the best performances…
- The Pilot’s Advisor Podcast
Markets & War: What Investors Should Know
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Global tensions have escalated following the…
- The Pilot’s Advisor Podcast
The Pros & Cons of the New Trump Savings Accounts
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ A new government-backed savings account for…
- The Pilot’s Advisor Podcast
Financial Lessons from a Snow Day
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ There’s something magical about a snow day…
- The Pilot’s Advisor Podcast
FedEx Pension, Windfalls, and the Pilot’s Legacy Playbook
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Big paydays can feel like smooth air, until…
- The Pilot’s Advisor Podcast
Demystifying Backdoor Roth IRAs with Zach Smith
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Ryan is joined by Zach Smith of Pilot Tax to…
- The Pilot’s Advisor Podcast
I’m 62: Should I File For Social Security Or Wait?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Turning 62 doesn’t feel like a big deal…
- The Pilot’s Advisor Podcast
Am I Behind in My Retirement Savings? Here's What You Can Do
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Nothing wrecks financial confidence faster…
- The Pilot’s Advisor Podcast
Should You Have More Than One Financial Advisor?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Having two financial advisors might seem…
- The Pilot’s Advisor Podcast
Southwest’s New NEC Roth Option: What Pilots Must Know
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Southwest pilots were hit with a major…
- The Pilot’s Advisor Podcast
2025 Year In Review: What Actually Mattered for Your Money
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ 2025 was loud… tariffs, market swings, tax…
- The Pilot’s Advisor Podcast
Cash Balance Plan or HRA? A Tough Call for United Pilots
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ United pilots are being asked to make a…
- The Pilot’s Advisor Podcast
The 5 Retirement Questions Smart People Ask
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ In this episode, Ryan continues last week’s…
- The Pilot’s Advisor Podcast
Why Better Questions Build Better Retirements
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Most people think the key to better…
- The Pilot’s Advisor Podcast
Planning for Retirement When You Marry Later in Life
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Getting married in your 50s often means…
- The Pilot’s Advisor Podcast
Turkey, Touchdowns, and Tax Planning?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ This week, Thanksgiving takes center stage…
- The Pilot’s Advisor Podcast
American Airlines Market-Based Cash Balance Plan: Should AA Pilots Opt-In?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ If you’re an American Airlines pilot, you’re…
- The Pilot’s Advisor Podcast
The Airline Pilot’s Hidden Tax Problem: Avoid a Massive RMD Shock
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ This Veterans Day episode of The Pilot’s…
- The Pilot’s Advisor Podcast
Flying Through Inflation: What Pilots Should Know About Mortgages and Interest Rates
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ As mortgage rates fluctuate and the real…
- The Pilot’s Advisor Podcast
Fuzzy Math Is Sabotaging Your Financial Future
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ You’ve probably said it before: “I ran the…
- The Pilot’s Advisor Podcast
If I Won’t Live to 90, Should I Claim Social Security Early?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ If your parents passed away relatively…
- The Pilot’s Advisor Podcast
Delta’s New Deferred Comp Plan: Smart Move or Tax Trap?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Delta Airlines has rolled out a new…
- The Pilot’s Advisor Podcast
5 Signs Pilots Might Be Richer Than They Think
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Most people don’t feel wealthy. But what if…
- The Pilot’s Advisor Podcast
What To Know About The “First Year Rule” Of Retirement
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ So, you’re retired. Now what? The “First…
- The Pilot’s Advisor Podcast
Long-Term Bullish, Short-Term Noise: A Market Reality Check
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Markets are unpredictable—sometimes rallying…
- The Pilot’s Advisor Podcast
Does Dave Ramsey’s 9-Step Retirement Plan Work for Pilots?
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Dave Ramsey is one of the most recognized…
- The Pilot’s Advisor Podcast
Gen X Pilots, It’s Your Time To Think About Retirement
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Cue the mixtape of Nirvana, Madonna, and…
- The Pilot’s Advisor Podcast
Rethink Your Thinking: The Case for Whole Life Insurance
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ What if the safest part of your portfolio…
- The Pilot’s Advisor Podcast
The Truth About Today’s Mortgage Market with Kelly Phillips
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Why do today’s mortgage rates feel worse…
- The Pilot’s Advisor Podcast
Autopilot to Retirement? What Pilots Need to Know About Target-Date Funds
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Target-date funds just passed $4 trillion in…
- The Pilot’s Advisor Podcast
Unlock Refunds Using 2025 Solar Credits with Ed Lyon
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ What if you could get a tax refund from…
- The Pilot’s Advisor Podcast
What Pilots Miss About Money Discipline
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ As a pilot, you're trained to anticipate…
- The Pilot’s Advisor Podcast
What Pilots Miss About Money Discipline
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ What makes one person obsess over saving for…