The Pilot’s Advisor Podcast

Hosted by Ryan Fleming

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234

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Nov 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

November 6, 2026Episode 23032 min

Tax Planning for Pilots: Strategies Beyond Filing Your Return (with Ed Lyon)

Book your Pilot Tax Strategy Session here: excelempire.com/pilots Pilots spend years building strong incomes and retirement accounts, but is anyone looking ahead at how taxes could affect all of it? Ryan sits down with Tax Strategist Ed Lyon to explore the difference between simply filing a tax return and proactively planning for what comes next. Their conversation challenges some common assumptions high-income W-2 earners make about how much control they really have over their tax picture. If taxes have always felt like something you simply have to accept, this episode may give you a different way to think about them. Here’s what we cover in this episode: 🧾 Tax Planning: Look beyond annual tax filing ✈️ W-2 Pilots: Explore options for high earners 🤝 Strategy Team: Add specialized tax expertise 📈 Retirement Taxes: Think beyond today’s deduction 🔮 Future Rates: Prepare for tax uncertainty 🩺 Planning Process: Diagnose before prescribing 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

October 29, 2026Episode 22914 min

How Do Pilots Know When It's "Safe" to Retire?

✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ "When can I retire?" might be the question Ryan gets asked more than any other. Some people are chasing an age. Others are chasing a number. Today, Ryan is breaking down what actually determines the answer. The date on the calendar or the number in the account might feel like the finish line, but neither one tells the whole story. That's what the planning process is actually for. Here’s what we cover in this episode: 📅 Retirement Date: Know what has to line up ✈️ Timing Factors: Weigh pension, savings, and healthcare 🧠 Retirement Mindset: Prepare for life after flying 📝 Income Planning: Build the retirement paycheck 🧾 Spending Needs: Know what retirement actually costs 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

October 15, 2026Episode 22811 min

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

October 8, 2026Episode 22723 min

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

October 1, 2026Episode 22622 min

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

September 25, 2026Episode 22512 min

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

September 17, 2026Episode 22425 min

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

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