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
✈️ 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,...
✈️ 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, lastin...
✈️ 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, ...
✈️ 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 mo...
✈️ 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 appro...
✈️ 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 somethin...
✈️ 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 bankin...
✈️ 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 con...
✈️ 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 po...
✈️ 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 a...
✈️ 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 li...
✈️ 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 daugh...
✈️ 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...
✈️ 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 retirem...
✈️ 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...
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...
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...
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 wo...
Today, Ryan’s taking us through some of the key concepts of The Psychology of Money by Morgan Housel. This book isn’t just about money strategies. It’s about why we make the choices we make, even when they don’t seem to make sense. You might find that your mindset is a bigger advantage than any investment tip.
Here’s what we cover in this episode:
📘 What Housel gets right about money behavior
🧠 The role of your mindset when it c...
If you've recently changed jobs, chances are your old 401(k) is still sitting right where you left it – out of sight and out of mind – and it could potentially cost you. In this episode, Ryan answers a question from a pilot who recently made the jump to a major airline and wants to know if he should roll over his old 401(k) or leave it where it is.
Ryan breaks down the pros and cons of keeping the 401(k) with a former employer vers...
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