The Pilot’s Advisor Podcast

Hosted by Ryan Fleming

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Episodes

225

Latest episode

Aug 2026

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About the show

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.

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60 recent

September 10, 2026Episode 22313 min

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

September 3, 2026Episode 22215 min

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

August 27, 2026Episode 2218 min

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

August 20, 2026Episode 21913 min

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

August 13, 2026Episode 22045 min

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

August 6, 2026Episode 2184 min

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

July 30, 2026Episode 2174 min

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

July 16, 2026Episode 21612 min

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

July 7, 2026Episode 21515 min

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

July 2, 2026Episode 21417 min

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