The Pilot’s Advisor Podcast

A Market Strategy for Pilots With Type A Personalities

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

Why The Psychology of Money Says Your Emotions Matter More Than Math

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 comes to money
🛑 The danger of “never enough” thinking
🧮 Reasonable vs. rational financial decisions
🚨 Why planning with a margin of error is non-negotiable
 
The Psychology of Money: Timeless lessons on wealth, greed, and happiness by Morgan Housel: https://shorturl.at/W8FEJ
 
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

Is It Bad to Leave My 401(k) Where It Is?

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 versus moving it into an IRA, and what smart investors should consider before making the call.
Here’s what we cover in this episode:
📂 What happens when you leave an old 401(k) behind
🔁 Why a direct rollover is usually better than a transfer
⚠️ Common mistakes that trigger taxes or penalties
✈️ What pilots need to know about retirement account 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

Mailbag: Market Crashes, Corrections, and Staying Calm

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 guidance on how to chart a steady course.
Here’s what we cover in this episode:
💡 The truth about timing the market
✈️ Diversification myths: are you as protected as you think?
📊 Rebalancing during downturns: risk or opportunity?
🧠 Emotional decisions vs. system-driven strategies
 
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

Spring Cleaning for Your Finances: A Marie Kondo Approach to Money

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 stocks could be holding you back
📦 Organizing investments by category, not location
🗑️ Letting go of fear of the future
⏰ One of the most valuable assets in retirement planning
 
Marie Kondo Netflix Trailer: https://www.youtube.com/watch?v=WvyeapVBLWY
 
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

I Went to the New York Stock Exchange - Here’s What I Learned

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’s what we cover in this episode:
📈 What advisors on the floor think about 2025’s market outlook
🎯 Why clarity and coaching matter more than timing
🧭 Why old-school investing strategies may no longer apply
⚡ How algorithmic trading is accelerating market volatility
 
0:00 – Intro
0:51 – AI & High Frequency Trading
3:09 – Is Volatility Is Here to Stay?
7:20 – Principles for the New Market
8:25 – Stops & Pivot Point Planning
9:41 – Being On The Floor on the NYSE
12:03 – Final Thoughts
 
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

What the Greats Say About Market Crashes

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.
Here’s what we cover in this episode:
📉 Buffett’s “greedy when others are fearful” lesson
🧠 We can be our own worst enemy
📊 Jack Bogle’s ultimate advice: “Stay the course”
⚠️ Why timing the market usually backfires
📚 An expert’s advice on handling unseen risk
 
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

April Fool’s: Beliefs That Fool Retirement Savers The Most

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:
💸 Healthcare costs are no joke in retirement
📉 How taxes fool more people than they realize
🧠 Why “guaranteed returns” are a red flag
🪙 Dividend chasing can backfire
 
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

Bracket Picks and Stock Myths

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 we cover in this episode:
🧠 Why emotional investing leads to poor decisions
📉 The surprising odds of stock-picking success
📈 Why diversification still beats “gut feeling”
⚠️ The hidden risks of being loyal to one stock
📚 How real market data can reframe your mindset
 
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

Retirement Lessons From The Masters

What does Augusta National have in common with your retirement plan? A lot more than you think. Ryan uses the game of golf—and the iconic Masters Tournament—as a powerful metaphor for achieving retirement success. We drive into key takeaways, like why consistency leads to better retirement results as opposed to risking it all for a “hole-in-one” and how diversification is just like using a full set of clubs.
Here’s what we cover in this episode:
🏌️‍♂️ Chasing “hole-in-one” hot stocks won’t win retirement
🧰 You need a full set of clubs – Diversify your investments & tax strategies
⚠️ Avoid the hazards – Taxes, inflation, and healthcare costs can derail your plan
🧠 Your advisor is your caddy guiding you through tough shots with clarity
 
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