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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

16:10

Automating Savings Outside of 401k For a Smarter...

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

2025/11/13

Most pilots automate their 401(k) savings without thinking about it, but what about everything outside that one account? Scott breaks down how to automate savings into the other tax buckets that will actually give you flexibility, control, and lower taxes in retirement. Discover why diversifying how and where you save could be the smartest way to unlock more financial options down the road. Here’s some of what we discuss in this episode: 🤖 Automated Savings: why automation matters beyond the

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12:56

Delta Pilots: Unlocking the Power of Your NQDC Plan

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

2025/11/06

In this episode, Scott breaks down the Delta Non-Qualified Deferred Compensation (NQDC) plan, showing how it differs from a traditional 401(k) and how you can strategically use it to manage your taxes and retirement income. He explains the eligibility rules, contribution limits, and how to decide if this plan fits into your overall retirement strategy. By the end of the episode, you’ll have a clear understanding of both the benefits and risks, so you can make informed decisions for your finan...

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15:07

The Market Is Scary Good. What Does That Mean For You?

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

2025/10/30

When the market feels unstoppable, it’s easy to wonder if now’s the time to invest or sit tight and wait for the next drop. In this episode, Scott explains what it really means when the market is “scary good” and how to stay grounded when emotions run high. Are you approaching retirement or just getting started? This episode will help you see through the hype and stick to your long-term plan. Here’s some of what we discuss in this episode: 📊 Market Emotions: how excitement and fear drive

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14:31

Are Bonds Back? What Pilots Need To Know in 2025

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

2025/10/23

Bonds used to be the ‘boring’ part of a portfolio. They were considered safe, steady, and not very exciting. But with yields at multi-decade highs, a lot of people are asking: Is now the time to give bonds a bigger role in your investment strategy? Scott explains how to think about bonds in today’s market, the difference between owning debt and owning equity, and why the timing of when you’ll need your money matters most. Bonds can provide income, balance, and peace of mind, but they’re not o...

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20:33

401(k) Misconceptions: What Pilots Need to Know About...

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

2025/10/16

Most people know their 401(k) is key to retirement, but few understand how each account type affects their taxes and long-term flexibility. This episode breaks down the differences between pre-tax, Roth, and after-tax contributions, helping you see how each fit into your overall strategy. Scott also shares how small shifts today can lead to major savings later. Tune in to make sure you’re using your 401(k) to its fullest potential! Here’s some of what we discuss in this episode: 💰401(k)

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14:20

Should You Have More Than One Financial Advisor?

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

2025/10/09

If having two financial advisors sounds like double the wisdom, think again. In this episode, Scott explains why splitting your money between multiple advisors can actually create confusion, gaps, and unnecessary risk in your financial plan. Using pilot and cockpit analogies, he breaks down how conflicting advice, overlapping investments, and missing coordination can lead to turbulence in your retirement strategy. Scott shares how one coordinated plan, one clear strategy, and one trusted advi...

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18:24

That Didn’t Age Well: Investment Predictions Gone Wrong

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

2025/10/02

Some financial gurus love to predict doom and gloom, but what happens when their “I told you so” doesn’t actually hold up? In this episode, Scott takes a hard look at the loudest voices in the industry and why chasing their bold claims often leaves investors worse off. Here’s some of what we discuss in this episode: 📰 Beware of fear-driven financial “gurus” 📉 Predictions of collapse rarely pan out 📊 Trust the data, not the noise ⏳ Patience and discipline beat market timing 🛡️ Building a

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17:35

The Truth About Downsizing in Retirement

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

2025/09/25

Downsizing in retirement often sounds like an easy decision, but it’s rarely that simple. In this episode, Scott breaks down some of the most common downsizing myths - like whether a smaller home really lowers monthly expenses - and explains why the numbers don’t always add up. Tune in for practical insights to help you weigh whether moving to a smaller home is truly the right choice for you. Here’s some of what we discuss in this episode: 🏡 Downsizing doesn't always lower costs 💰 Using...

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15:21

Are September & October Really Bad Months to Invest?

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

2025/09/18

September and October often get a bad rap in the investing world, but are they truly risky months? In this episode, Scott breaks down the truth behind these "turbulent" months. While data shows September's historical slight negative returns, it’s important to peel back the layers. If you're nearing retirement, it's crucial to understand the data and avoid knee-jerk reactions to monthly trends. Here’s some of what we discuss in this episode: 📉 September’s performance: Is it as bad as it

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19:33

How To Catch Up If You're Late To The Retirement Party?

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

2025/09/11

Falling behind on retirement savings can feel overwhelming, especially if you’re only just hitting your financial stride in your 30s, 40s, or even 50s. In this episode, Scott tackles the big question: How do you catch up if you feel late to the retirement party? From military pilots transitioning into airlines to career changers carrying student loans, many people wonder if they’ve missed their window to build a stronger nest egg. The good news? With the right strategy, time, and income, you ...

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19:36

College or Retirement? Why Many Parents Are...

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

2025/09/04

According to a recent survey, the emotional and financial burden of paying for college often exceeds expectations. And it’s affecting everything from retirement plans to mental health. In this episode, Scott unpacks what families are really facing and how to make smarter decisions that won’t derail your own future. Here’s some of what we discuss in this episode: 💰 Why pausing retirement savings can be a costly mistake 🎓 The cost of college vs. return on investment 👨‍👩‍👧 New survey data on

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16:12

Are You Wealthier Than You Think? 5 Wealth-Building...

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

2025/08/28

Most people don’t feel wealthy. But what if your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think. And none of them involve yachts or private jets. In this episode, Scott analyzes the habits that signal real, lasting wealth and what to do if you are (or aren’t) on the right track. Here’s some of what we discuss in this episode: 💰 Emergency funds: your safety net for life’s

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18:46

Pilots: Can You Pass This Retirement Planning Quiz?

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

2025/08/21

The kids may be heading back to class, but it’s not a bad time for adults to hit the books too, especially when it comes to retirement. So, let’s test your knowledge with a quick financial pop quiz and see how ready you really are. Here are the quiz questions for today: 📝 At what age do you get full Social Security if born after 1960? 📝 Max IRA contribution for those 50+ in 2025? 📝 Which retirement account requires RMDs? 📝 What does the 4% rule mean in retirement planning? &...

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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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