The Pilot’s Advisor Podcast

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

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

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

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 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

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

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 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

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

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

If there’s ever been a great example of why you stay invested and avoid trying to time the market, it would be these recent market movements from tariff news. After days of sharp declines, the announcement that there will be a 90-day pause on tariffs for 75 countries and increased pressure on China led to an instantaneous pop upwards. In this quick update, we’ll discuss how emotional decision-making can derail a portfolio and the hidden risks of going to cash. Every day of big gains or sharp losses is a reminder of the power of discipline and the cost of hesitation. Here’s what we cover in this episode: 💸 Why going to cash too early can cost you big 🧭 Lessons from COVID, 2008, and other major downturns 📆 Why 2025 might finish stronger than you think 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

The news of Trump’s tariffs has caused global markets to go into a tailspin, and that means panic has started to set in for many investors. Seeing red numbers across your portfolio is never easy, but what if you saw this as an incredible opportunity rather than a time to get out of the market? Today we’ll talk about how long-term investors can use these dips as a chance to increase contributions and take advantage of short-term volatility. Here’s what we cover in this episode: 📉 Market downturns = buying opportunities for the long-term 💰 Increase contributions during market dips to maximize growth 🛑 Don’t let panic lead to rash decisions 🧳 Plan for sequence of returns risk and the impact of market volatility on retirement 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 2025 a bad year to retire? With headlines swirling about market volatility, federal layoffs, and a possible recession, it’s a question many pre-retirees—especially pilots—are asking. If you were targeting this year for a retirement date, let’s find out if Ryan thinks pilots should still retire or put their plans on hold. Here’s what we cover in this episode: 💼 Retirement plans should include built-in protection for volatility 🔁 Diversification and risk alignment are critical pre-retirement steps 🧠 Don’t make emotional decisions—stick to the plan 📊 A good plan works whether the market is up, down, or sideways 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

With markets off to a volatile start in 2025, many investors are feeling uneasy. But should you be worried? Ryan took a break during a recent trip to an advisor conference to share some thoughts on the recent market pullback, explaining why it’s normal, healthy, and even an opportunity for long-term investors. If you’re concerned about the latest market turbulence, please reach out and let’s have a discussion. Here’s what we cover in this episode: 0:00 - Intro 1:00 – Fear and greed 3:27 – Buying opportunity 5:51 – It’s like flying 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

The thought of a market crash will often make investors rethink their portfolio and move into cash. That’s what one American Airlines pilot reached out to us about recently. He has concerns about the market so half of his 401K is in cash, but now he wants to know when he should start investing it again. Today we’re going to answer that question and have a broader discussion about the risks of trying to time the market. Here’s what we cover in this episode: 0:00 - Intro 0:32 – Today’s question 2:50 – Changes as you approach retirement 7:22 – How investing has evolved 8:45 – Conservative doesn’t equal safe 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

We haven’t lacking headlines over the past six months but the craziness can provide some valuable lessons for investors. In this episode, we take a closer look at the recent fluctuations in the financial markets and the emotional responses of investors during turbulent times. Understanding the purpose of your investments is crucial. Many investors fall into the trap of reacting impulsively to headlines, often overlooking the bigger picture of their financial goals. By focusing on long-term strategies, you can mitigate the emotional turmoil that often accompanies market fluctuations. Here’s what we cover in this episode: 0:00 – Looking back on 2024 1:00 – Bumpy start to 2025 2:12 – Emotional reactions 4:30 – Maintaining a long-term view 6:29 – The best investors 8:58 – Understanding the market 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

In an era where retirement depends on an individual’s ability to save, the statistics tell us that America has a real problem. Ryan saw a few stats on tv recently that raised some major concerns, and it’s time to address the root of the issues. Today we’ll share the numbers that caught our attention and talk about the steps pilots need to be taking to ensure they aren’t falling behind. Here’s what we cover in this episode: 0:00 - Intro 1:30 – Are pilots in better shape? 3:58 – Savings tools 8:13 – Forced discipline 11:15 – Getting help 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

Fresh off another Super Bowl appearance, Andy Reid is a legendary head coach known for his strategic brilliance and leadership in the NFL. But what if we told you that his insights could also apply to financial planning and retirement strategies? In our latest podcast episode, we’ll share four bits of wisdom from Andy Reid draw parallels between his coaching philosophy and essential financial lessons. Here’s what we cover in this episode: 0:00 - Intro 2:20 – Quote 1 3:49 – Quote 2 4:58 – Quote 3 7:23 – Quote 4 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

This video explains why trying to time the market is a risky and often costly strategy for investors. It highlights how emotional decision-making, fear, and greed lead to buying high and selling low—hurting long-term returns. Historical data shows that missing just a few of the market’s best-performing days can drastically reduce overall gains. Instead of market timing, experts emphasize the benefits of a disciplined, long-term investing approach focused on diversification and staying invested. The key takeaway: time in the market beats timing the market. 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

The stock market saw a huge pullback in the technology sector with the arrival of DeepSeek, a new Chinese AI platform. What lessons should we be learning from what’s happening in the market and how does this change investment strategies? Today we’re joined by Lee Hyder of Lee Hyder & Associates to discuss the emotional reactions that often accompany such news and how they can lead to impulsive decisions among investors. Here’s what we cover in this episode: 0:00 – DeepSeek market pullback 3:00 – What did we learn? 7:12 – One powerful lesson to remember 10:38 – Strategies for 2025 12:37 – Emotional decisions 18:08 – DIY investors 23:09 – Are you aggressive enough? 26:47 – Evolving with technology 32:21 – Fees vs 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