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PODCAST

The Wealthy Pilot"s Podcast: Financial Flight Controls for Today"s Commercial Airline Pilots

Welcome to The Wealthy Pilot"s Podcast: Financial Flight Controls for Today"s Commercial Airline Pilots, where we navigate the skies of financial success with your host, Scott Osborn, The Pilot"s Planner. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott"s expertise we tackle

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All Episodes

29:48

Top 3 Rental Property Mistakes Pilots Should Avoid

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/08/14

This week, Scott sits down with Jason Watson from WCG CPAs and Advisors to talk about the top 3 mistakes high-income pilots should avoid when investing in rental properties. As pilots and other high earners look for ways to diversify their income beyond their primary careers, rental properties offer a powerful path to building lasting wealth- if you approach it the right way. Here’s some of what we discuss in this episode: 🛫 Why pilots’ schedules make rentals a uniquely attractive investment

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12:38

The 7 Deadly Investment Sins (Pt. 2) Fear, Greed &...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/08/07

We’re back for Part 2 of the “7 Deadly Sins of Investing,” and these final three may be the hardest to overcome, because they’re not technical; they’re emotional. Scott explores how fear, greed, and impatience can quietly creep into our financial decisions and derail long-term success. These aren’t just feelings; they’re patterns that lead to poor timing, unnecessary risk, and abandoning a perfectly good plan. Here’s some of what we discuss in this episode: 🛣️ How emotional reactions pull

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14:28

The 7 Deadly Sins of Investing (Pt. 1) – Market...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/07/31

We’re kicking off a special two-part series on the “7 Deadly Sins of Investing.” In this first installment, Scott unpacks four of the biggest behavioral missteps investors make, especially when emotions run high or market headlines dominate the news. If you're over 50 and starting to think seriously about protecting your nest egg, this is one episode you won’t want to miss. Here’s some of what we discuss in this episode: 🌪️ Why market timing usually backfires 🧺 The trap of owning “too much”

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12:19

Investing During All-Time Highs: Strategies For Success

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/07/24

The market’s hitting record highs, but does that mean it’s too risky to invest right now? In this episode, Scott breaks down what all-time highs actually mean for long-term investors. You’ll hear how short-term fear often leads to poor decisions and why zooming out can help you stay grounded. Here’s some of what we discuss in this episode: 📈 Why investing at all-time highs isn’t as scary as it seems ⏳ Why time in the market beats timing the market 📉 What short-term pullbacks really mean for

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28:42

Financial Advisor Reacts To Dave Ramsey’s 9-Step...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/07/17

Dave Ramsey is one of the most recognized voices in personal finance. His 9-step retirement plan is simple, direct, and built for mass appeal. But is it really the best path for your retirement? You'll hear where Scott agrees, where he diverges, and what every pilot needs to know about balancing tax strategies, health care costs, and when to bring in an advisor. Here’s some of what we discuss in this episode: 🚨 What mass-market advice misses + how intentional planning can change ...

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16:30

The Big Beautiful Bill Breakdown: What It Means For You

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/07/10

The Big Beautiful Bill (BBB) is here, and with it comes tax updates that could shape your financial strategy for years to come. In this episode, Scott and Marc break it all down in clear, practical terms: what stays, what changes, and what it means for pilots, high earners, and retirees alike. But here’s the catch: many of these changes are temporary, so smart planning now could make a big difference later. Here’s some of what we discuss in this episode: 🧠 Taking advantage of today’s low tax

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21:30

5 Types of Independence Every Retiree Needs

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/06/26

As we celebrate the Fourth of July, this episode explores what independence truly looks like in retirement, beyond fireworks and freedom. Scott dives into five core areas of independence that every retiree (or future retiree) should be aiming for as they prepare for life after work. It's not just about having enough money, but having control, peace of mind, and a plan that works. Here’s some of what we discuss in this episode: 📆 Retiring on your schedule, not because you have to 💰 Ditch...

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20:55

Smarter Estate Planning: Why You Need a Plan Now

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/06/19

Estate planning is something we all know we should do, but it’s often pushed to the bottom of the list. In this episode, Scott shares a heartbreaking real-life story: a close friend’s brother died suddenly at 42. Recently divorced, with two young sons and no estate plan in place, the aftermath was a painful legal tangle. It’s a tragic example of what happens when planning is left undone, and how the people you love end up bearing the weight. Listen in as Scott talks through the essentials of ...

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19:39

Retirement Breaking News: The 4% Rule Gets a Makeover?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/06/12

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision? Here’s some of what we discuss in this episode: 📏 Why the 4% rule became the “default” retirement planning guide 🔍 What the 4.7% update really means (and doesn’t

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17:24

The Lazy Way to Retire? Let’s Talk Target-Date Funds

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/06/05

Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? Here’s some of what we discuss in this episode: 🧭 Why defaulting to a target-date fund could misalign with your goals 📉 How these funds reduce risk—but possibly too early or too much ⚠️ The hidden costs and risks that go beyond fees 🎯 What to do i...

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20:48

5 Ways Wishful Thinking Can Damage Your Retirement

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/05/29

A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Scott’s walking through five common examples of wishful thinking that can quietly damage your retirement, and how you can build a plan that protects your future instead of relying on luck. Here’s some of what we discuss in this episode: 🧾 A major tax myth you need to face 🏠 Does cost of living ever drop? ⚠️ The dangers of DIY Planning 🎢 Market return

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15:01

Why Type A Investors Should Probably Do Less

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/05/22

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, Scott breaks down the challenges Type A investors face when market volatility strikes and why a high-performance mindset doesn’t always translate into bett...

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18:44

Am I Saving Too Much For Retirement?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/05/08

We’ve all heard that Americans don’t save enough for retirement, but what if the opposite is true for you? Can you save too much? In this episode, Scott tackles a surprising but important question raised by a listener: “Are we over-saving at the expense of living now?” As an airline professional, it can be easy to feel like you’re doing too little, or maybe even too much. This conversation helps you find the balance. Here’s some of what we discuss in this episode: 💸 Can you save too much for

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14:26

Are We Headed Towards a Recession? How to Prepare...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/05/01

Recession fears are back in the headlines, but should they be back in your financial plan, too? We’re in the middle of earnings season and data is coming in, so Scott will tackle the question: Are we heading for a recession? With shrinking GDP, rising inflation, and uncertain interest rate moves by the Fed, we’ll try to decipher what the latest economic signals really mean and discuss how investors should think about their portfolios right now. Here’s some of what we discuss in th...

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15:14

Retirement Lessons From The Masters (Part 2)

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/04/24

In part two of this special Masters series, Scott takes us to the “back nine”- the final stretch of retirement planning where pressure builds and smart decisions matter most. From avoiding risky plays in your 50s and 60s to understanding how emotions can derail your strategy, Scott lays out what it really means to finish strong. Here’s some of what we discuss in this episode: ⛳ Why “Amen Corner” = age 50+ in your financial life 🎯 Avoiding the urge to overcorrect under pressure 🧠 Discipline

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12:58

Retirement Lessons From The Masters (Part 1)

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/04/14

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, we’re teeing up a few key lessons from the course and how they translate into smarter planning for your financial future. Here’s some of what we discuss in this episode: ⛳ What golf teaches us about investing ⚠️ Avoiding overconfidence after short-term wins 📉 Why steady strategy beats risky moves 🏌️‍♂️

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14:26

Liberation Day: Is 2025 A Bad Time To Retire?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/04/03

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy amidst federal layoffs and tariffs. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it? Here’s some of what we discuss in this episode: 0:00 – Intro 2:08 – Headline response to market 3:49 – Sequence of returns risk 6:19 – Different market sectors 8:07 – The tendency to chase performance 9:36 – Investo...

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52:49

Infinite Banking: The Smarter Way to Build Wealth

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/03/20

What if you could become your own banker and take control of the way you finance your life? Today we’re excited to welcome on Brian Moody and Hans Tooey of Remnant Finance to explore the Infinite Banking Concept- a financial strategy designed to help you protect, save, and grow your wealth without relying on traditional banks. Here’s some of what we discuss in this episode: 0:00 – Intro 1:00 – Background on our guests 4:50 – The Infinite Banking concept 13:25 – Flipping financing 22:03 ...

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11:24

How Side Gigs Impact Your Retirement Portfolio

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/03/13

Thinking about starting a side gig? Many pilots explore side hustles like real estate or passion projects, but how do these extra income streams impact retirement planning? Are there tax advantages you should be taking advantage of? And how can you ensure your side hustle is working for you, not creating extra stress? In this episode, Scott breaks down the impact of side gigs on your long-term financial plan. We’ll discuss the most common side hustles for pilots, the tax benefits of structuri...

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13:43

Do Smart Investors Need a Financial Advisor?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/03/06

If you’ve spent years successfully managing your own investments, do you really need a financial advisor? Scott works with a lot of highly skilled, intelligent professionals. So, for someone like this, is working with an advisor just an extra expense, or could it actually add real value? In this episode, we break down when and why even experienced investors might benefit from professional guidance and when they’re probably fine on their own. Here’s some of what we discuss in this episod...

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