The Pilot’s Advisor Podcast

✈️ 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...

The market’s been shaky and pilots are wondering how the volatility impacts their retirement and investment decisions. In this special mailbag edition of the show, we’ll answer real questions from aviators facing turbulence in their retirement plans. Whether they’re near retirement, sitting on cash, or watching everything dip at once, today’s questions all circle one theme: how do I respond when markets get rocky? Join us for guida...

Spring is in the air and for some, that means it’s time for spring cleaning. Marie Kondo is considered an expert in tidying and decluttering, and wrote the book, “The Life-Changing Magic of Tidying Up.” In today’s episode, Ryan brings a Marie Kondo-inspired approach to finances, helping you declutter, get organized, and let go of what no longer “sparks joy.”

Here’s what we cover in this episode:

💸 Why emotional attachment to stoc...

Ryan just got back from the New York Stock Exchange, and he’s sharing what it was like to stand on the floor during the iconic closing bell. Go behind the scenes to learn more about the modern trading environment, one that’s quieter, more high-tech, and dominated by algorithms. Ryan discusses what percentage of trades are now executed by computers, and what that means for volatility, investor behavior, and long-term planning.

Here’...

When the market is crashing, it's easy to feel like you're the only one who's ever felt this anxious. But the truth is, some of the greatest investors in history have lived through chaos, and they left behind wisdom that still applies today. In this episode, Ryan responds to wisdom from experts like Warren Buffett, Benjamin Graham, and Jack Bogle to remind us how to think, act, and stay grounded when everything feels uncertain.

Her...

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. Ryan unpacks the financial “pranks” people may fall for—from too-good-to-be-true returns to myths about Social Security, taxes, and healthcare in retirement.

Here’s what we cover in this episode:

💸 ...

When it comes to investing, are you picking winners or just playing favorites? In this episode, Ryan breaks down how our emotional biases, gut instincts, and misplaced confidence can sabotage even the best financial intentions.

Using bracket-building and sports betting as a metaphor, Ryan explores how chasing individual stocks is a lot like guessing tournament upsets: unpredictable, addictive, and often disappointing.

Here’s what w...