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The Pilot’s Advisor Podcast

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Rating
★★★★☆
4
from
12 reviews
This podcast has
232 episodes
Language
English
Publisher
Ryan Fleming
Explicit
No
Date created
2019/04/02
Latest episode
2026/10/15
Average duration
17 min.
Release period
8 days

Description

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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Podcast episodes

Check latest episodes from The Pilot’s Advisor Podcast podcast


A New Bill Would Lower the Social Security Retirement Age… For Some
2026/10/15
✈️ 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
Adapting to Change Without Losing Your Cool
2026/10/08
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
Conversation Starters: Questions Pilots Should Ask To Reveal Financial Truths
2026/10/01
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
Inflation, Purchasing Power & the Risk of Being Too Conservative
2026/09/25
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
The Pilot Retirement Reality Check: 2026 Version
2026/09/17
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
Rejection, Career Detours &… A Secret Crush!?
2026/09/10
✈️ 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
Why People Keep Working In Their Retirement Years
2026/09/03
✈️ 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
Cell Phones Changed More Than Communication
2026/08/27
✈️ 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
What Happens When Pilots DIY Their Retirement Plan
2026/08/20
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
FedEx Pilots: Don’t Spend That Lump Sum Until You Hear This
2026/08/13
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
Is Your Advisor Talking Over Your Head?
2026/08/06
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
How Much Money Is Too Much in the Bank?
2026/07/30
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
Dave Ramsey Says You Can Withdraw 8% - Here's What the Research Actually Says
2026/07/16
✈️ 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
Trump Accounts: Free Money or Financial Distraction?
2026/07/07
✈️ 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
What Your 4th of July Traditions Can Teach You About Money
2026/07/02
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

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