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
4 days ago
4 days ago
✈️ 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
4 days ago
4 days ago
✈️ 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
Thursday Sep 04, 2025
Gen X Pilots, It’s Your Time To Think About Retirement
Thursday Sep 04, 2025
Thursday Sep 04, 2025
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Cue the mixtape of Nirvana, Madonna, and Prince… Gen X, it’s your turn to get ready for retirement. And the stakes are high. You were the first 401(k) generation, hit by two major market crashes, and now you’re entering retirement with more financial uncertainty than the Boomers before you. But you also have something else: resilience. If you're a pilot between your mid-40s and early 60s, it’s time to get serious about what retirement will look like for your generation.
Here’s what we cover in this episode:
🛫 Gen X pilots are the first true 401(k) generation
📉 Market crashes and inflation have reshaped retirement confidence
💡 Taxes & Inflation: the hidden forces that can drain your nest egg
🔑 Control comes from preparation, not last-minute scrambling
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
Thursday Aug 28, 2025
Rethink Your Thinking: The Case for Whole Life Insurance
Thursday Aug 28, 2025
Thursday Aug 28, 2025
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
What if the safest part of your portfolio wasn’t bonds, but something with guarantees, liquidity, and tax advantages? In this special episode, we’re sharing Ryan’s recent appearance on the Wealth Warehouse podcast, where he sat down with David Befort and Paul Fugere to talk about whole life insurance, infinite banking, and why these strategies deserve a second look.
Here’s what we cover in this episode:
💡 Whole life insurance as a fixed-income alternative
🔑 Infinite banking and the “and asset” concept
📉 Protecting against sequence of returns risk
✈️ Pilots’ unique retirement planning challenges
🏦 Why premiums aren’t bills but wealth-building deposits
Check out the Wealth Warehouse YouTube channel: https://www.youtube.com/@Thewealthwarehousepodcast
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
Thursday Aug 21, 2025
The Truth About Today’s Mortgage Market with Kelly Phillips
Thursday Aug 21, 2025
Thursday Aug 21, 2025
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Why do today’s mortgage rates feel worse than they really are? When it comes to real estate and mortgages, timing and perspective make all the difference. In this episode, Ryan sits down with Kelly Phillips, Mortgage Expert and Branch Manager at Fairway Mortgage, who brings more than 25 years of experience to the conversation. With a front-row seat to the shifting housing market, Kelly shares her insights on today’s rates, buyer hesitation, and what really determines the best time to buy.
Here’s what we cover in this episode:
📉 Why rates feel high (but aren’t historically)
🏠 How inventory keeps today’s market a seller’s game
⏳ Why waiting could cost more than buying now
🔄 The refinance conversation: when it does and doesn’t make sense
📊 Lessons from 2008, 2020, and today’s market
Contact Kelly Phillips, Mortgage Expert & Branch Manager at Fairway Home Mortgage
843-209-8805
kelly.phillips@fairwaymc.com
www.yourfairwaylender.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
Thursday Aug 14, 2025
Autopilot to Retirement? What Pilots Need to Know About Target-Date Funds
Thursday Aug 14, 2025
Thursday Aug 14, 2025
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? In this episode, Ryan breaks down why target-date funds, despite their popularity, might not be the best fit for pilots navigating toward retirement.
Here’s what we cover in this episode:
🛫 Why target-date funds are now the default, but not always the best
🧾 What’s inside a target-date fund (and what’s missing)
🚨 The major risks of a “one-size-fits-all” retirement plan
💸 How layering target-date funds leads to lack of diversification
🔍 Why pilots need a customized investment and distribution strategy
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
Thursday Aug 07, 2025
Unlock Refunds Using 2025 Solar Credits with Ed Lyon
Thursday Aug 07, 2025
Thursday Aug 07, 2025
✈️ 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 2022, using a move you make in 2025? In this episode, Ryan sits down with one of the biggest names in tax strategy: Ed Lyon. You may have seen him on CNN, Fox News, CNBC, or MSNBC, or read one of his books. Dubbed “America’s Funniest Tax Guy,” Ed has trained thousands of CPAs and advisors to help clients legally pay less, and now he’s revealing a little-known solar tax strategy that many pilots could benefit from, but only if they act before the window closes.
Here’s what we cover in this episode:
⚡️ Solar Hack = Instant Refunds?
💰 Tax Credits from Thin Air?
🕵️♂️ 2025’s Legal Loophole Revealed
✈️ Why Pilots Have the Edge
🔥 Act Before This Window Slams Shut
If you want to follow up with Ed, you can email him directly here: edwardalyon@gmail.com
Learn more about what he does here:
https://edwardalyon.com/
https://taxmasternetwork.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
Thursday Jul 31, 2025
What Pilots Miss About Money Discipline
Thursday Jul 31, 2025
Thursday Jul 31, 2025
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
As a pilot, you're trained to anticipate risk and build backup systems, but are you applying that same mindset to your financial future? In this episode, Ryan answers a smart listener question about legacy planning, life insurance, and tax-efficient wealth transfer. Ryan explains why many pilots overlook permanent life insurance, like an overfunded whole life policy, until later in life, and how that delay can limit its full potential.
Here’s what we cover in this episode:
🛩️ Why pilots think differently about risk and how to use that to your advantage
💵 Overfunded whole life: a powerful (but underused) strategy
🧾 When insurance becomes a tax planning tool
🚫 Why waiting too long makes it more expensive
More on Overfunded Whole Life: www.IBC4Pilots.com
How We Help Eliminate Sequence of Returns Risk:
https://www.youtube.com/watch?v=vSsR7Km5XRw
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
Thursday Jul 24, 2025
What Pilots Miss About Money Discipline
Thursday Jul 24, 2025
Thursday Jul 24, 2025
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
What makes one person obsess over saving for the future while another spends freely, and sometimes recklessly, in the moment? Today, Ryan explores how personal wiring, background, and mindset influence financial behavior. Drawing from personal experience, client stories, and even conversations with his teenage daughter, Ryan explains why small, consistent choices lead to real freedom later in life. This episode will help you better understand your financial habits, and how to shift them for long-term peace and purpose.
Here’s what we cover in this episode:
✈️ How pilot culture shapes financial habits
💰 Starbucks or stock? The decision that compounds
📈 What over-savers and over-spenders miss
🧾 Taking care of legacy planning matters before it's too late
🎯 The secret power of forced discipline
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
Thursday Jul 17, 2025
Mailbag: Trading Options? Think Again, Captain
Thursday Jul 17, 2025
Thursday Jul 17, 2025
✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Today’s story is all too familiar: a pilot nearing retirement, intrigued by a cockpit conversation about options trading, only to watch his portfolio nosedive.
In this episode, Ryan gets candid about why jumping into options (especially in your 50s) might not be the best option for a secure retirement. With decades of experience guiding pilots, Ryan explains how speculation, stock picking, and chasing “hot tips” can wreck even the best-laid glide paths.
Here’s what we cover in this episode:
🚫 Why options trading is playing with fire
📉 A cautionary tale: one pilot’s 60% loss
🧠 The psychology behind poor investing choices
✈️ “Don’t take financial advice from a pilot”
🛑 How to avoid sabotaging your own retirement
Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/
The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2