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.
Podcast Description
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
Nov 19, 2025
Nov 19, 2025
17 min
✈️ 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 facing a major decision: whether to participate in the newly announced Market-Based Cash Balance Plan. Ryan is joined once again by Zach Smith from Pilot Tax to break down how the plan actually works, what AA pilots need to know, and the long-term tax consequences many pilots aren’t thinking about. Most importantly, we explore how this decision affects retirement flexibility, future RMDs, and your ability to control your own investment strategy.
Here’s what we cover in this episode:
🛩️ What AA’s new plan really is: how the Market-Based Cash Balance Plan works behind the scenes
📉 Lack of control & conservative investing: why the pooled structure limits growth
💥 The tax time-bomb problem: how spillover contributions worsen future RMDs
💰Roth vs. spillover strategy: why many AA pilots should consider opting out
📊 A better long-term approach: controlling taxes, liquidity, and retirement flexibility
Get in touch with Zach: https://pilot-tax.com
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Nov 13, 2025
Nov 13, 2025
39 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
This Veterans Day episode of The Pilot’s Advisor features Zach Smith from Pilot Tax for a deep dive into one of the biggest challenges facing airline professionals: retirement tax planning. Ryan and Zach explain why airline contracts that fund 18–19% of pay into 401(k)s create future RMD headaches, how Roth strategies can help you gain long-term control, and why taxable brokerage accounts can be a powerful, flexible alternative to overfunded retirement plans.
Here’s what we cover in this episode:
💰 The unique tax challenges that pilots face
🧾 Why deferring taxes isn’t always smart🚀 Roth accounts = long-term freedom📊 Taxable brokerage accounts offer flexibility⚖️ True tax diversification = balance + control
Get in touch with Zach:
info@pilot-tax.com
317-984-7666
https://pilot-tax.com/
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Oct 30, 2025
Oct 30, 2025
34 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
As mortgage rates fluctuate and the real estate market adjusts, pilots and investors alike are wondering, what’s next? In this episode, Ryan sits down with Christopher Zarnik, a fellow FedEx pilot and mortgage broker, to unpack today’s housing and lending landscape. Christopher also shares practical advice on navigating today’s market and invites listeners to reach out with their mortgage or homebuying questions.
Here’s what we cover in this episode:
📈 Inflation Reality: how rate hikes and cuts shape the housing market
💰 Refinancing Rules: when it makes financial sense (and when it doesn’t)
🏦 Mortgage Fees 101: which costs are negotiable and how to lower them
🔒 Lock It In: why waiting for lower rates can backfire
💸 Borrow Smart: use the bank’s money and keep your assets working
Positive Rate Mortgage: https://www.positiveratemortgage.com
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Oct 23, 2025
Fuzzy Math Is Sabotaging Your Financial Future
Oct 23, 2025
Oct 23, 2025
18 min
✈️ 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 numbers; I should be fine.” But what if your math is lying to you? Today, Ryan exposes the “fuzzy math” that can quietly sabotage your financial future. Drawing on lessons from aviation and decades of experience helping pilots plan for retirement, he shows how to balance big-picture thinking with precise financial navigation. Don’t settle for “it should be fine,” learn how to make sure your math actually adds up.
Here’s what we cover in this episode:
✈️ Fuzzy Math & Flying Lessons: why “winging it” doesn’t work in retirement
💸 The 4% Rule Debate: why it’s more complicated than it looks
🧾 Fees & Value: how advisors can add 3%+ net benefit even after costs
🚨 Sequence of Returns Risk: understanding timing and volatility impact
🪂 Pilot Principles Applied: discipline, big-picture awareness, and staying calm
0:00 – Fuzzy Math in Financial Planning
1:24 – Pilots Are Trained To See the Big Picture
4:19 – Fuzzy Math in Mutual Funds
6:24 – The 4% Safe Withdrawal Rate
12:20 – Tax Concerns in Retirement
14:10 – Capital Gains Tax and Investment Returns
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Oct 16, 2025
Oct 16, 2025
13 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
If your parents passed away relatively young, it’s natural to wonder whether you’ll face the same fate, and whether that should change how you claim Social Security. In this episode, Ryan discusses how life expectancy, health, pensions, and even your trust in the system can shape the right decision. He breaks down the opportunity costs of claiming early versus waiting, real pilot scenarios, and why the best answer usually requires looking at your full financial picture. If you’ve ever wrestled with whether to take Social Security now or later, this episode will give you clarity and perspective.
Here’s what we cover in this episode:
📉 How family history influences Social Security timing
✈️ Why pilots face unique health and longevity challenges
⏰ The pros and cons of claiming early
🛡️ The role of pensions in deciding when to claim
🏛️ Concerns about Social Security cuts or changes
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Oct 9, 2025
Oct 9, 2025
19 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Delta Airlines has rolled out a new non-qualified deferred compensation plan for pilots, and it’s raising big questions across the flight deck. To help us all better understand what this means, we’ve invited Zach Smith of Pilot Tax to break down how it works and whether it’s a smart financial move. Before you opt in, make sure you understand the risks, rewards, and long-term implications of this new Delta offering.
Here’s what we cover in this episode:
✈️ The details about Delta’s new deferred comp plan
💵 Potential tax benefit by deferring income into lower-tax years
⚠️ The risk of overloading your pre-tax retirement bucket
💰 How fixed income in retirement affects Medicare
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Oct 2, 2025
Oct 2, 2025
21 min
✈️ 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 your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think. And none of them involve yachts or private jets. Let’s analyze the habits that signal real, lasting wealth, and what to do if you are (or aren’t) on the right track.
Here’s what we cover in this episode:
💵 Emergency fund strength: why liquidity is a sign of wealth
🚫 Living below your means: the “millionaire next door” mindset
📈 Strategic investing: the power of systematic savings
🛫 Long-term focus: ignoring short-term turbulence for lasting success
Kiplinger Article: 7 Signs You’re Secretly Getting Rich (and Don’t Even Know It)
https://www.kiplinger.com/personal-finance/signs-youre-secretly-getting-rich-and-dont-even-know-it
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Sep 25, 2025
Sep 25, 2025
17 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
So, you’re retired. Now what? The “First Year Rule” suggests that many of your best retirement months will happen in the first year. It’s a pivotal time to set the tone for a fulfilling retirement, emotionally, physically, and financially for the years ahead. Today, Ryan explores how to navigate this critical phase, offering practical insights to help you create a strong foundation for a retirement that’s rewarding, balanced, and full of purpose.
Here’s what we cover in this episode:
💰 Understand your income needs for retirement
✈️ How travel and new experiences can impact your finances
🏠 Test out your long-term plans before committing
💡 Build routines and purpose to thrive in retirement
💬 Have a conversation with your advisor about the first year
Retire Pilots - https://retirepilots.com
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Sep 11, 2025
Sep 11, 2025
13 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Markets are unpredictable—sometimes rallying on bad news, other times tumbling for no clear reason. So how do you stay focused when headlines scream about rate cuts, job reports, and volatility?
In this market update, Ryan weighs in on the Fed’s expected rate cut, why September and October are historically tricky months for markets, and why short-term noise shouldn’t derail your long-term strategy. What are the possible outcomes of different rate cut scenarios and what will the lasting impact of artificial intelligence and automation be on the market?
Here’s what we cover in this episode:
📉 Fed rate cut watch – 50 bps could boost markets; no cut may trigger declines.
📆 Seasonal volatility – September/October historically shaky, but context matters.
🤖 AI and automation – Long-term bullish trends, but potential job disruption.
🕒 Time horizon > age – Investment allocation should match when you’ll actually need the money.
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Sep 11, 2025
Sep 11, 2025
18 min
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Dave Ramsey is one of the most recognized voices in personal finance. His 9-step retirement plan is simple, direct, and built for mass appeal. But is it really the best path for your retirement? On today’s show, Ryan digs into where he agrees, where he disagrees, and what he thinks is missing from Dave Ramsey’s approach entirely.
Here’s what we cover in this episode:
📋 Ramsey’s 9-step plan: simple but limited
🛫 Pilots need strategies beyond “one-size-fits-all”
⛽ “Always take more gas than you need” — Ryan’s analogy for oversaving to build flexibility
🔑 Sometimes liquidity beats paying off your mortgage
🏥 Healthcare and Social Security require nuance, not broad strokes
Retire Pilots - https://retirepilots.com
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
Pilot Tax - https://pilot-tax.com/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2









