The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots
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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/
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📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html As the year comes to a close, it’s the perfect time to pause, reflect, and reset. Scott looks back on the wins, challenges, and lessons from 2025, both financially and personally, while setting the stage for smarter planning in 2026. Are you ready for the new year? Tune in to make sure y...
📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Scott breaks down United Airlines’ cash balance plan for pilots and explains how it addresses overfunded 401(k) accounts. He covers how the plan works, the benefits of tax-deferred growth, and how to decide between the Cash Balance Plan and United’s HRA/RHA options. By the end of this ep...
📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html As the new year approaches, Scott breaks down the key planning numbers and contribution limits pilots need to understand before 2026 kicks off. This episode is all about checking your settings, updating your strategy, and making sure you’re taking advantage of every opportunity. As 2025 ...
📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Scott breaks down the brand-new Market-Based Cash Balance Plan (MBCB) and what this decision means for American Airlines pilots hitting their 401(k) limits. The goal isn’t to push pilots one way or the other, but to help you understand what’s really at stake before that opt-in deadline h...
📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Gratitude has a way of grounding us, shaping our attitude, and influencing how we approach our financial lives. Discover how gratitude transforms not just our outlook, but our wealth. In this episode, Scott unpacks why a grateful mindset is key to building financial health, making confid...
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 ...
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...
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 poor...
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...
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) Basic...
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...
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 plan ...
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...
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 seems?...
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 ...
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 par...
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 ...
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? &...
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 ...
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 peo...
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