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 common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://thepilotsplanner.com/
Episodes
52 episodes
Are You Wealthier Than You Think? 5 Wealth-Building Habits for Pilots
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...
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16:12
Pilots: Can You Pass This Retirement Planning Quiz?
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.Her...
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18:46
Top 3 Rental Property Mistakes Pilots Should Avoid
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 properti...
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29:48
The 7 Deadly Investment Sins (Pt. 2) Fear, Greed & Impatience
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 financi...
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12:38
The 7 Deadly Sins of Investing (Pt. 1) – Market Timing, Diversification Mistakes & More
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...
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14:28
Investing During All-Time Highs: Strategies For Success
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 decision...
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12:19
Financial Advisor Reacts To Dave Ramsey’s 9-Step Retirement Plan
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...
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28:42
The Big Beautiful Bill Breakdown: What It Means For You
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 m...
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16:30
5 Types of Independence Every Retiree Needs
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 f...
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21:30
Smarter Estate Planning: Why You Need a Plan Now
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, wit...
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20:55
Retirement Breaking News: The 4% Rule Gets a Makeover?
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...
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19:39
The Lazy Way to Retire? Let’s Talk Target-Date Funds
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?&...
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17:24
5 Ways Wishful Thinking Can Damage Your Retirement
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 retireme...
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20:48
Why Type A Investors Should Probably Do Less
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, an...
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15:01
Am I Saving Too Much For Retirement?
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 th...
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18:44
Are We Headed Towards a Recession? How to Prepare Yourself
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 sh...
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14:26
Retirement Lessons From The Masters (Part 2)
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 em...
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15:14
Retirement Lessons From The Masters (Part 1)
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...
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12:58
Liberation Day: Is 2025 A Bad Time To Retire?
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...
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14:26
Infinite Banking: The Smarter Way to Build Wealth
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 Bankin...
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52:49
How Side Gigs Impact Your Retirement Portfolio
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...
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11:24
Do Smart Investors Need a Financial Advisor?
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 e...
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13:43
What Do Proposed Tariffs Mean For Your Portfolio?
The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy...
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10:19
Money Questions Every Couple Needs To Discuss
Valentine’s season is all about love, but let’s be honest, money plays a huge role in any relationship. Whether you’ve been together for decades or are just starting out, financial stress can put a strain on even the strongest partnerships. So,...
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14:15
Need Cash Fast? The Best (and Worst) Ways for Pilots to Borrow Money
Whether it's for a home remodel, a major purchase, or just to cover unexpected expenses, where should you turn for cash when you need it? In today’s episode, Scott breaks down the three primary avenues for obtaining cash: 401(k) loans, Home Equ...
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9:10