The Pilot’s Advisor Podcast

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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

✈️ 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 Get in Tough with Ed Lyon: https://edwardalyon.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

✈️ 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

✈️ 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

✈️ 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

✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Raising kids used to follow a predictable pattern: they grow up, move out, and you finally get the house to yourself. But for many pilots today, that “empty nest” moment keeps getting delayed. In this episode, Ryan dives into the emotional and financial turbulence of raising adult children while planning for retirement. If your kids are still living at home, boomeranging back, or needing long-term financial help, Ryan shares what that really means for your retirement runway. Here’s what we cover in this episode: 🏡 Why adult kids are staying home longer 💸 How to support without sabotaging your plan 🛫 Retirement prep when your “nest” is full 🚧 Setting healthy financial boundaries Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ In this episode, Ryan answers a thoughtful listener question from Shirley, a pilot who recently inherited a parcel of land from her uncle. With a mortgage still on her home and retirement a few years away, Shirley wonders: should she sell the land to become debt-free or hold on to it and explore other options? Ryan shares the key considerations when deciding what to do with inherited real estate, especially when it’s not an income-producing asset. Here’s what we cover in this episode: 🏡 Land vs. liquidity? (It depends on your goals) 💸 Should you rush to pay off your mortgage? 📉 When “dead assets” slow your growth 🧾 Why details matter in inheritance decisions 📊 Why timing and interest rates make all the difference 💸 Home Equity & Mortgage YouTube video: https://www.youtube.com/watch?v=j37WkBP0Yd4

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision? In this episode, Ryan explores the implications of the updated withdrawal rate, highlighting the crucial caveats that may make or break your retirement strategy. Here’s what we cover in this episode: 🧐 What the 4% Rule Really Meant (and Why It’s Shifting) 💣 How Inflation, Taxes & Risk Impact Your Withdrawal Rate ⚖️ Pros & Cons of Fixed-Income-Heavy Portfolios 🪣 How bucket strategies and guardrails protect your plan 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

In this episode, Ryan delivers a “pilot report,” offering a timely look at today’s economic turbulence. From global conflict and rising interest rates to inflation pressure and a shifting housing market, Ryan explains how these forces are shaping your financial flight path, and what adjustments you might need to stay on course. Ryan also shares practical, down-to-earth financial advice, especially geared toward young adults, recent grads, or anyone feeling a bit behind. Here’s what we cover in this episode: 📉 How high interest rates are freezing upgrades and first-time buyers 💵 Start small: $50 a month + compound interest can work magic 🔁 Why consistent investing beats stock-picking and market timing ⚠️ What new grads often get wrong and how to avoid it 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Today we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. In this episode, Ryan explains why Type A pilots, used to control, precision, and quick decisions, can be their own worst enemies when markets get volatile. Here’s what we cover in this episode: 🧠 When doing less is actually doing more 🧮 Risk vs. reward: are you overcorrecting? ✈️ What pilots get wrong about control and timing 🧍‍♂️ Why solo investors may need a wingman 📉 Turn bear markets into long-term opportunity 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