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.
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- 🇰🇪KE · Investing#175350 to 3.1K
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350 to 3.1K🎙 ~2x weekly·226 episodes·Last published 6d ago - Monthly Reach
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700 to 6.3K🇺🇸71%🇰🇪29% - Active Followers
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385 to 3.5K
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 10/15/26 | A New Bill Would Lower the Social Security Retirement Age… For Some | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ A new bill in Congress would let some workers claim full Social Security benefits at 60, seven years earlier than today’s rules stipulate. That's a big headline. But it's just a proposal, and it lands in the middle of a much bigger debate about Social Security's future. Today, Ryan reacts to the news and talks about what it means for your planning. Social Security is going to keep making headlines, and the rules may change at some point. But planning around what's proposed isn't the same as planning around what's real. The best approach is a plan that can adjust either way. Here’s what we cover in this episode: 👷 New Proposal: Consider earlier benefits for workers 🤔 Funding Concerns: Question long-term system sustainability 🧮 Social Security Math: Understand growing planning uncertainty ✈️ Pilot Health: Factor career wear into retirement 📅 Claiming Strategy: Reevaluate when benefits should begin 🧭 Flexibility: Plan around multiple possible outcomes 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 | 11m 34s | ||||||
| 10/8/26 | Adapting to Change Without Losing Your Cool | What if the biggest step forward is letting go of what you can’t control? In this episode, Ryan reflects on personal growth, staying grounded amid uncertainty, and adapting to a changing world. The common thread is learning where to focus your energy and where to stop letting fear, noise, or other people’s opinions hold you back. Here’s what we cover in this episode: 🧠 Personal Growth: Push past insecurity and self-doubt 🎙️ Putting Yourself Out: Stop fearing others’ opinions 📱 Market Noise: Avoid doom-and-gloom rabbit holes 📉 Investor Emotions: Don’t make reactive financial decisions 🤖 Artificial Intelligence: Learn where AI can help ⚠️ AI Limitations: Keep expertise and judgment involved 🔄 Adaptability: Embrace change instead of resisting it AI Chatbots Give Wrong Financial Answers Most of the Time Study https://www.investmentnews.com/fintech/ai-chatbots-give-wrong-financial-answers-most-of-the-time-study-finds/268267 The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About https://amzn.to/4rPhtwB 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 | 23m 11s | ||||||
| 10/1/26 | Conversation Starters: Questions Pilots Should Ask To Reveal Financial Truths | Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely. Here’s what we cover in this episode: 🎯 Purpose: Building meaningful routines after flying 🧞 Financial Genie: Identifying your biggest money stressors 💭 Money Lessons: Reflecting on past financial decisions ❤️ Emotions: Connecting feelings with financial choices 🧭 Personal Goals: Discovering what truly matters most ✈️ Pilot Toolkit: Resources for retirement preparation 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 | 22m 44s | ||||||
| 9/25/26 | Inflation, Purchasing Power & the Risk of Being Too Conservative | Inflation doesn't arrive as a bill in the mail, but over time it can quietly take a serious bite out of your purchasing power. Ryan uses a humorous quote about the rising cost of a haircut to explain a much bigger retirement-planning problem: your money has to keep pace with what life will cost in the future. For pilots planning decades into the future, the challenge is finding the right balance between protecting what you've accumulated and maintaining enough growth potential to preserve purchasing power throughout retirement. Here’s what we cover in this episode: 📉 Inflation quietly erodes purchasing power. 💵 Too much cash can create its own risk. 📈 Retirement assets need long-term growth potential. ✈️ Inflation hits pilots and airlines especially hard. ⚖️ Being too conservative 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 | 12m 21s | ||||||
| 9/17/26 | The Pilot Retirement Reality Check: 2026 Version | Retirement planning today doesn't look like it did even a decade ago, let alone the way it looked for our parents. On this episode, Ryan provides several realities you need to be aware of in 2026 to build toward a successful retirement. Retirement isn't the same finish line it used to be, and pretending otherwise makes it harder to plan for. The realities change. A good plan should be able to change with them. Here’s what we cover in this episode: ⏳ Longer Retirement: Preparing for the possibility of 30 years or more after leaving the cockpit ✈️ Pilot Deadline: Planning around the mandatory end of a major-airline flying career 🔄 Career Transition: Finding meaningful work or purpose after airline flying ends 🏥 Healthcare Costs: Preparing for coverage before Medicare and expenses later in life 💔 Gray Divorce: Understanding how a late-life separation can reshape retirement finances 🧭 Moving Target: Building a plan that can adapt as taxes, benefits, technology, and life circumstances change 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 | 25m 55s | ||||||
| 9/10/26 | Rejection, Career Detours &… A Secret Crush!? | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Ever had a job that humbled you, but quietly set the stage for everything that came next? Ryan puts Walter on the spot with a hilarious story about his stepmom’s crush on him, which leads into real talk about rejection, first jobs, and knowing what you don’t want to do. They unpack how detours, mentors, and “closed doors” can actually move you closer to your calling. In the end, it’s a reminder that success is rarely a straight line, and the people who nudge you along the way might matter more than the plan you started with. Here’s what we cover in this episode: ❤️ Garnet’s Crush: Ryan’s stepmom has a new crush 💼 Early Career Struggles: Rejection can redirect careers 🔥 Stay Hungry: Humble jobs build motivation 🧭 Career Direction: Learn what you don’t want 🤝 Helpful People: Mentors can change trajectories 📈 Long Game: Success takes time and experience 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 | 13m 36s | ||||||
| 9/3/26 | Why People Keep Working In Their Retirement Years | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ More people in their 60s and 70s are staying on the job than ever before, and it's not always about the money. Ryan digs into the real reasons retirees keep showing up to work. Working longer isn't automatically the wrong call. Sometimes it's exactly right. The real question is whether it's a choice or a fallback. That's worth figuring out before you assume the answer. Here’s what we cover in this episode: 🤝 Social Connections: Work provides built-in community 🏠 Home Transition: Retirement changes daily routines 💪 Healthy Habits: Structure supports better discipline 📋 Plan Doubts: Uncertainty delays retirement decisions ⏳ Early Planning: Start years before retirement ✈️ Pre-Flight Planning: Preparation reduces future stress 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 | 15m 51s | ||||||
| 8/27/26 | Cell Phones Changed More Than Communication | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ What started as a nostalgic conversation about first cell phones quickly turned into something much bigger. Ryan looks back at early mobile phones, instant messaging, and how technology gradually made all of us more available all the time. Technology may have changed how we communicate, but the value of honest guidance has not changed much at all. Here’s what we cover in this episode: 📱 First Phones: Brick phones bring nostalgia 💬 Instant Messaging: Communication changed incredibly fast ⏰ Always Available: Technology erased some boundaries 🏈 Tough Love: Good coaching requires honesty 🎯 Better Advice: Challenge can create progress 📊 Financial Planning: Accountability still matters 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 | 8m 47s | ||||||
| 8/20/26 | What Happens When Pilots DIY Their Retirement Plan | There's an entire television network dedicated to doing things yourself — home renovation, landscaping, interior design, all of it. And the DIY mentality is genuinely admirable. But when it comes to retirement planning, the stakes of a bad install are a little higher than a crooked backsplash. Today, Ryan talks about what DIY planning actually looks like in practice. DIY has its place. But some projects are worth calling a professional, especially when the cost of getting it wrong follows you for the next thirty years. Here’s what we cover in this episode: 🛠️ DIY Mentality: Independence does not guarantee better outcomes 💼 DIY vs. Advisors: Lower fees may come with additional problems 📉 Common Mistakes: Stock picking and timing create risk 😰 Investor Emotions: Greed and fear undermine discipline 🧭 Professional Guidance: Objective advice can improve direction 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 | 13m 50s | ||||||
| 8/13/26 | FedEx Pilots: Don’t Spend That Lump Sum Until You Hear This | FedEx pilots are about to receive a significant lump sum, and what happens next could have a lasting impact on their financial future. In this episode, Ryan is joined by David Befort to discuss a strategy pilots may want to understand before that money gets spent, transferred, or committed elsewhere. A lump sum can disappear quickly, but the right strategy may allow it to keep working for years to come. Here’s what we cover in this episode: ✈️ September Lump Sum: FedEx pilots have an important decision ahead 🏦 Infinite Banking: IBC offers an alternative way to put a windfall to work 🛡️ Whole Life Insurance: Properly structured policies can provide guarantees, liquidity, and flexibility 📈 Long-Term Advantages: The goal is to keep more money working inside your financial system 📞 Next Steps: Education and individual planning come before implementation Resources for this episode: EY Article: https://www.ey.com/en_us/insights/insurance/how-life-insurers-can-provide-differentiated-retirement-benefits Infinite Banking for Pilots by David Befort Infinite Banking for Pilots: Befort, Mr David: 9798320594668: Amazon.com: Books Connect with David: https://www.davidbefort.com/ www.ibc4pilots.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 | 45m 17s | ||||||
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| 8/6/26 | Is Your Advisor Talking Over Your Head? | Ever felt like your advisor is speaking a different language? Ryan unpacks what to do when financial jargon gets in the way of understanding your money. He talks about why clear communication matters more than technical terminology and when it might be time to ask for clarification. or a second opinion. Tune in to find out if your advisor’s lingo is a red flag or just a translation issue. Here’s what we cover in this episode: 🗣️ Clear Communication: Good advisors adapt to their audience 🖍️ Running Joke: Ryan keeps explanations simple and memorable 🔍 Second Opinion: Ongoing confusion may signal concern 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 | 4m 26s | ||||||
| 7/30/26 | How Much Money Is Too Much in the Bank? | Ever wonder if your “safe” cash is actually holding you back? In this episode, Ryan answers a listener’s question from a pilot who has built up $150,000 in cash but is hesitant to move it because of the security it provides. He explains the difference between liquidity and leaving too much money idle. Stick around to find out if your cash strategy is helping, or quietly hurting, your future. Here’s what we cover in this episode: 💧 Liquid Security: Access matters without sacrificing growth 🏦 Checking Balance: Keep only monthly spending needs 📈 Emergency Funds: Long-term reserves may deserve investment 🔓 Liquid Accounts: Taxable investments remain easily accessible 🧰 Retirement Toolkit: Pilots can request planning resources 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 | 4m 34s | ||||||
| 7/16/26 | Dave Ramsey Says You Can Withdraw 8% - Here's What the Research Actually Says | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Dave Ramsey has built one of the most recognized brands in personal finance. Millions of people have followed his advice out of debt and into savings. But when it comes to how much you should pull from your retirement accounts each year, Ramsey takes a position that some financial professionals find hard to get behind. Today, we break it down: what Dave says, what the research says, and what Ryan actually thinks. Here’s what we cover in this episode: ✈️ Pilot-Level Planning: Complex finances need tailored advice. 📉 Eight Percent Risk: Market averages ignore retirement volatility. 📊 Four Percent Rule: A conservative research-based starting point. 🎯 Custom Strategy: Pensions and spending needs matter. 🔥 Sequence Risk: Safe buckets protect during downturns Ramsey’s 8% Retirement Rule Sounds Nuts At First 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 | 12m 34s | ||||||
| 7/7/26 | Trump Accounts: Free Money or Financial Distraction? | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ Trump Accounts are here, but are they really the best way to jump-start your child’s financial future? Ryan explains what these new 530A Trump Accounts are and how they stack up against other options. While the concept of teaching kids to invest early is powerful, Ryan questions whether these accounts are truly the most efficient tool for long-term planning. Before you rush to open one, find out if this is a savvy move or just overhyped “free money.” Here’s what we cover in this episode: 💰 Trump Accounts 101: What are they and how do they work? 🧾 Account Details: Rules, eligibility, and ownership 📈 Investment Choices: Comparing other savings vehicles 🛠️ Practical Steps: What parents should consider Trump Accounts: The Pilot’s Preflight Briefing: https://tinyurl.com/muwa6zrv https://trumpaccounts.gov 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 | 15m 38s | ||||||
| 7/2/26 | What Your 4th of July Traditions Can Teach You About Money | This year's Fourth of July carries a little extra weight as we celebrate 250 years of American independence, and that's worth a moment. But between the hot dogs, the parades, and the fireworks, we started thinking about how many of our favorite holiday traditions have a pretty natural financial parallel. So that's what Ryan’s doing today… and the comparisons might surprise you. Here’s what we cover in this episode: 🎆 Market Volatility: Fireworks can be unpredictable 🌭 Emergency Funds: Be ready when life happens 🗽 Financial Freedom: Independence takes discipline 📈 Long-Term Investing: Avoid speculation and gambling 💰 Forced Savings: Consistency creates opportunity 🛫 Pilot Planning: Freedom through preparation 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 | 17m 54s | ||||||
| 6/25/26 | SDBAs vs. Target Date Funds – The 401K Mistake Most Pilots Make | If you're a pilot, there's a good chance your retirement savings are sitting in a target date fund you selected years ago and haven't thought about since. The problem is that the fund doesn't know anything about your pension, your spouse's income, your retirement timeline, or the unique challenges pilots face. In this episode, Ryan explores a little-known feature inside many 401(k) plans and shares research that may change the way you think about retirement planning. Here’s what we cover in this episode: 📉 DIY Penalty: The cost of going alone 🧠 Behavior Gap: Emotions hurt investor returns 💧 Cost Leaks: Small expenses compound over time ✈️ SDBAs Explained: More options inside your 401(k) 📋 Case Study: Personalized planning in action 🚀 Pilot Advantage: Retirement planning beyond average 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 | 26m 03s | ||||||
| 6/18/26 | In Your 50s & 60s? Here's What "Risk" Should Look Like Right Now | Many pilots assume that as retirement gets closer, they should automatically become more conservative with their investments. But according to Ryan, that's not always the right move. He explains why risk management has less to do with your age and more to do with your time horizon, income sources, and retirement goals. If you're trying to strike the right balance between growth, protection, and income planning, Ryan shares a valuable framework for thinking about risk. Here’s what we cover in this episode: ✈️ Risk Management: Matching risk to your situation 📅 Time Horizon: Why age isn't the deciding factor ⚖️ Asset Allocation: Finding the right balance 🚨 Common Mistakes: When being too conservative backfires 💰 Income Planning: Building retirement paychecks 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 | 9m 14s | ||||||
| 6/11/26 | What Does Smart Risk Actually Look Like in Your 30s & 40s? | Risk is unavoidable. The real question is whether the risk you're taking makes sense for where you are in life. In this episode, Ryan explores three common financial personalities among people in their 30s and 40s, and the steady contributor quietly building wealth over time. If you're trying to figure out whether you're taking too much risk—or not enough—Ryan offers a practical framework for evaluating where you stand and where you want to go. Here’s what we cover in this episode: 🚀 Aggressive Investing: Why speculation isn't a strategy 💵 Playing It Too Safe: The hidden risk of cash 📈 Power of Compounding: Time is your greatest asset ⚖️ Finding Balance: Taking risk with a purpose ✈️ Pilot Perspective: Why discipline beats prediction 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 | 7m 56s | ||||||
| 6/4/26 | Maverick, Goose, and the Financial Danger Zone | It's summer and nothing says summer quite like Tom Cruise as Maverick soaring across the sky in Top Gun. This year marks the 40th anniversary of the original film, and with Tom Cruise's birthday on July 3rd, Ryan figured it was the perfect excuse to revisit some of the most iconic quotes from the franchise and see what they have to say about your financial life. Because Maverick didn't become the best by flying blind and hoping for the best. He had a plan, a co-pilot, and enough self-awareness to know when the risk was worth it. Here’s what we cover in this episode: 🚀 Need for Speed: Avoiding get-rich-quick investing 😎 Ego & Mistakes: Keeping emotions in check ⚠️ Danger Zone: Understanding risk and volatility 📜 Future Planning: Preparing for life's uncertainties 🤝 Find a Co-Pilot: Why guidance matters in 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 | 19m 08s | ||||||
| 5/1/26 | FedEx Pilots’ Guide to TA 2026: The Smart Tax Moves | In this episode, Ryan is joined once again by CPA Zach Smith to unpack the FedEx TA 26 retirement choices, this time from a tax and long‑term planning angle. Instead of just chasing the biggest paycheck, they explore how pensions, 401(k)s, and new cash-balance options can create either freedom or a “ticking tax time bomb” in retirement. If you’re a FedEx pilot facing this decision, this conversation will challenge how you think about taxes, flexibility, and your family’s legacy. Here’s what we cover in this episode: 💰 Three Choices: Each leads to very different outcomes 🧨 Tax Pressure: Income stacking creates future problems 🛡️ Guaranteed Income: Stability comes with tradeoffs 🧾 Limited Control: Some plans restrict your flexibility 🚀 More Flexibility: After-tax dollars give you options 💡 Smarter Mix: Roth + brokerage create long-term advantages FedEx TA26 Retirement Option Tool: https://retirepilots.com/fedex-ta26-tool/ FedEx TA 2026: 3 Retirement Options That Could Change Everything https://pilotsadvisor.podbean.com/e/fedex-ta-2026-3-retirement-options-that-could-change-everything/ 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 | 32m 35s | ||||||
| 4/20/26 | FedEx TA 2026: 3 Retirement Options That Could Change Everything | USE THIS: FedEx TA26 Retirement Option Tool. Check out our educational modeler - https://retirepilots.com/fedex-ta26-tool/ FedEx pilots are facing a major decision with three very different retirement options, each with long-term implications for income, flexibility, and legacy in the 2026 tentative agreement. While the details are still evolving, the choice between a pension-style income, a hybrid approach, or a more flexible contribution-based plan could shape your financial future for decades. In this episode, Ryan breaks down each option in simple terms, highlighting the pros, cons, and key factors to consider. Here’s what we cover in this episode: ✈️ Three options offer very different retirement outcomes 💰 Taxes play a major role in long-term results 📊 Control vs. guarantees is a key tradeoff ⏳ Longevity impacts which option makes sense 🧠 Personal goals matter as much as the math Get the Summary of Proposed FedEx Retirement Changes: https://retirepilots.com/wp-content/uploads/2026/04/FedEx_TA_2026_Retirement_Plan_Options-PDF-Recap-for-Show-Notes.pdf 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 | 31m 38s | ||||||
| 4/16/26 | What Pilots Are Googling About AI & Retirement | AI isn’t just a buzzword, it’s quickly becoming one of the biggest unknowns in retirement planning. Pilots in their 50s and 60s are actively searching for answers about how this technology could impact their future. Ryan tackles the most common AI-related questions pilots are Googling right now, and where human judgment still plays a critical role. Here’s what we cover in this episode: 📊 Portfolio Exposure: Many investors don’t realize how much AI exposure they already have ⚖️ Risk vs Opportunity: AI could drive growth, but also increased volatility ⏳ Early Retirement Thinking: Fear shouldn’t be the reason you retire early 🧠 AI Planning Tools: Helpful for information, but not a replacement for strategy 🚧 Human Element: Emotion, context, and experience still matter in decision-making See the Morgan Stanley prediction: https://finance.yahoo.com/news/morgan-stanley-predicts-ai-won-073000488.html?guccounter=1 Invesco’s Winter 2026 DC Participant Pulse Survey: https://401kspecialistmag.com/dc-participants-open-to-private-markets-and-ai-with-guardrails-invesco-survey/ 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 | 20m 52s | ||||||
| 4/9/26 | Will AI Replace Pilots in the Next 5 Years? | AI is changing everything right now, and aviation isn’t going to be immune to that. The question is… what does it actually mean for you as a pilot? Ryan breaks down what AI is really going to do to the cockpit, what parts of the job might change, and why he doesn’t see pilots going anywhere anytime soon. But there are some shifts coming, and they’re worth paying attention to. We also zoom out and talk about how AI is impacting the broader economy, what that could mean for your portfolio. Here’s what we cover in this episode: 🛫 AI in aviation: Enhancing systems, not replacing pilots anytime soon 👨✈️ Pilot demand: Shortage continues to drive pay and workload changes 🤖 AI in society: Creating winners and losers across industries 📈 Investing impact: Diversification matters more in uncertain environments 🧠 Human element: Judgment and experience still critical in flying and planning 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 | 12m 30s | ||||||
| 4/2/26 | Life Insurance For Pilots: Term, Whole, or Universal Life? | ✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ We got a great question from a listener: “What’s better? Term life insurance, universal life, or whole life?” Straightforward question. Not a straightforward answer, especially if you’re in your 50s. In this episode, Ryan walks through how life insurance decisions evolve over time and why what worked earlier in your career may not hold up as retirement approaches. Tune in to hear the key differences between term, whole, and universal life, and how it may impact your retirement. Here’s what we cover in this episode: 🛡️ Protection focus: Protect family, retirement, and reduce sequence risk 🕒 Term vs. permanent: Term is cheap; permanent stays and builds value 💰 Why whole (not universal): Guarantees, tax advantages, safer structure ✈️ Retirement jet engine: Backup income source in down markets 📚 Pilot resources: Tools, books, and education for deeper planning Resources for this episode: IBC4Pilots.com Becoming Your Own Banker: Unlock the Infinite Banking Concept by Nelson Nash: https://amzn.to/3NLTdfj How we help eliminate Sequence of Returns Risk: https://www.youtube.com/watch?v=vSsR7Km5XRw Permission to Spend: Maximize Your Retirement with the Best-Kept Secret in Personal Finance: https://amzn.to/4uIfXgG 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 | 17m 51s | ||||||
| 3/26/26 | War with Iran, Energy Prices, and Your Money: What You Need to Know | When global conflict makes headlines, it’s natural to wonder what it means for your money. In this episode, Ryan breaks down how markets are reacting to the ongoing conflict in Iran and what investors should be paying attention to right now. While volatility and rising energy costs can create concern, the bigger picture often tells a very different story. Ryan reminds us that short-term headlines don’t always change long-term outcomes. Here’s what we cover in this episode: 🌍 Market Reaction: How the Iran conflict is impacting markets and energy prices 😬 Investor Emotions: Why fear and uncertainty lead to poor decisions 📈 Long-Term View: Markets historically recover—and often create opportunity 📉 Slow Decline: Why this “death by a thousand cuts” feels worse than it is 📊 War & Markets: What history shows about investing during conflict 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 | 10m 42s | ||||||
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Chart history for The Pilot’s Advisor Podcast
Peaked at #175 in KE, currently #175 in KE.
| Market | Genre | Peak | Current | Trend |
|---|---|---|---|---|
| KE | — | #175 | #175 | — |
Chart Positions
1 placement across 1 market.
Chart Positions
1 placement across 1 market.