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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

12:58

Additional Places to Save Beyond Your 401(k) in 2025

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

2025/01/09

We’ve all heard about the importance of contributing to a 401(k) for retirement. But is it really enough on its own? For some, maybe it is, but it’s always wise to explore other options and keep an open mind.In this episode, Scott dives into a range of strategies that could help you build wealth for retirement, from Roth IRAs and the "backdoor" Roth to life insurance, real estate investments, and tax loss harvesting. Here’s some of what we discuss in this episode:0:00 – Intro1:05 – Figur...

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11:34

Where Pilots Should Contribute Their Earnings In 2025

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

2025/01/02

In this episode of the Wealthy Pilots Podcast, Scott Osborn breaks down where to contribute your money in 2025. Learn why diversifying your savings across Roth, tax-deferred, and taxable accounts can help you retire with more flexibility and fewer tax headaches. Discover simple tweaks that can make a big difference for your future—whether you’re just starting or already maxing out your 401(k).Here’s what you’ll learn on this episode:•The importance of diversifying retirement savings across di...

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10:20

United Airlines Pilots Reject Their 2024 Contract?

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

2024/12/26

In this episode of The Wealthy Pilot's Podcast, we discuss recent developments in market-based cash balance plans within the airline industry, focusing on United Airlines pilots’ rejection of their proposed 2024 contract. Scott and Marc break down how these unique retirement plans work and why pilots are concerned about their long-term financial benefits.They also explore the trade-offs between opting into market-based cash balance plans versus taking the money upfront and investing it indepe...

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11:54

What Fed Rate Cuts Could Mean for Your Finances in 2025

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

2024/12/19

In this episode of The Wealthy Pilot's Podcast, Scott and Marc break down the latest Federal Reserve rate cuts and explore what they mean for the economy, businesses, and financial planning. With interest rates on the decline, they discuss how this could impact mortgage affordability in 2025 and why large companies are likely to make more aggressive investments. They also dive into the potential opportunities these rate cuts present for investors. Throughout the conversation, Scott and M...

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18:19

End of Year Financial Planning for Airline Pilots

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

2024/12/12

As the year draws to a close, it's the perfect time to take a step back and review your financial planning. In this episode, Scott discusses important year-end strategies to help you optimize your finances before December 31. He covers key topics like Roth conversions, tax loss harvesting, HSA contributions, and other essential tasks that could make a big impact on your financial situation.Plus, Scott offers a look ahead to 2025, with insights into changes in tax brackets, contribution limits...

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10:38

Protecting Your Finances During Airline Turmoil

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

2024/12/05

In this episode of The Wealthy Pilots Podcast, Marc and Scott dive into the current state of the airline industry and chat about both the challenges and successes some airlines are facing. From record travel numbers to struggling airlines like JetBlue and Spirit, they discuss how rising fuel costs and labor issues are affecting profitability. With larger airlines doing well, smaller regional carriers are left to fight for better contracts and compensation. Whether you’re dealing with fur...

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12:23

Got A Side-Hustle? Make Sure You Learn About BOIR...

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

2024/11/21

In Scott’s line of work, it’s common to see pilots who are juggling a side hustle or business. That’s why this week, we’re diving into the Beneficial Ownership Information Report (BOIR), part of the Corporate Transparency Act (CTA). What is it, why does it matter, and how does it impact pilots and their side hustles?Join us as Scott breaks down the penalties for non-compliance and what you need to do to ensure you’re squared away before the January 1 deadline. If you’re a pilot balancing a ca...

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14:49

Post-Election Check In: Talking TCJA, DOGE, Tariffs &...

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

2024/11/14

Election season has finally come to a close and we’re turning our focus to the potential impacts on the economy and financial planning in the coming years. While many of the proposed changes are still in the early stages and subject to change, today’s episode dives into some of the major topics that could shape 2025 and beyond. From tax policy to corporate strategies, it’s time to start thinking ahead.Here’s some of what we discuss in this episode: 0:00 – Intro0:38 – A Tax Cuts and Jobs ...

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14:21

What Elections Mean For Taxes

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

2024/11/07

Election week 2024 is upon us, so today, we’re taking a close look at what political shifts could mean for taxes and your overall financial strategy. With the national debt skyrocketing to $36 trillion, the results of this election could significantly influence future tax policies. Join us as we explore the differing approaches to taxation from the two major political parties and how these changes might shape the economic landscape in the years ahead.Here’s some of what we discuss in this epi...

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16:02

Do Elections Really Impact Your Investments?

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

2024/10/31

Halloween isn't the only thing spooking people this week. With the election just days away, many investors are wondering how this season will impact their portfolios. So in today’s episode, we’re going to spend some time talking about the impact of political shifts on the stock market. Here’s some of what we discuss in this episode:0:00 – Intro3:39 – Not letting politics influence your investment decisions 6:53 – External factors that will impact the market9:16 – Procrastinating inv...

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14:03

Career Contingency Strategies for Pilots

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

2024/10/24

In the world of aviation, pilots are trained to handle unexpected challenges like turbulent weather or technical malfunctions. Yet, one area that often gets overlooked is planning for potential setbacks in their own careers. In today’s episode, we’re discussing strategies to help pilots stay prepared for unexpected career disruptions.Scott and Marc focus on two major areas of concern for pilots: furloughs and the loss of a Class 1 Medical Certificate. By dedicating just a short amount of time...

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11:12

Disability & Long-Term Care Planning for Pilots

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

2024/10/17

As we continue our discussion on contingency planning, today's focus shifts to disability and long-term care. Disability insurance is a vital component of a pilot's financial strategy. Given the unique nature of their profession, pilots face specific risks that can impact their ability to work. It’s important for them to ensure their income is adequately protected, especially in the event of unforeseen circumstances.Long-term care is another critical area that many overlook until they are nea...

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13:54

Contingency Planning- Creating Your “When I Die” Plan

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

2024/10/10

Having both an “if I die young” and a “when I die” plan is something we all need. In this week’s episode of the Wealthy Pilots Podcast, Scott and Marc discuss an often avoided but essential topic: contingency planning. While it might not be the most enjoyable conversation, it's one that can’t be ignored. Tune in as we discuss the importance of having a comprehensive strategy in place, particularly for pilots and families with young children. From determining the right life insurance cove...

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12:45

What Is Contingency Planning? (And Why It’s Important!)

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

2024/10/03

In life, not everything goes according to plan. Whether you're flying a plane or managing your finances, unexpected challenges can arise at any moment. That’s why it’s so important to have a plan for when things go wrong.In today’s episode, we’re talking about contingency planning- what it is and why it’s important for your financial life. We'll explore how being prepared for the unexpected can help you maintain control and confidence in your financial decisions. If things take an unexpected ...

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11:25

Tax Prep Vs Tax Planning: What’s The Difference?

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

2024/09/26

Most of us think about taxes once a year, around April 15th. We gather our documents, either to do it ourselves or hand them over to a CPA. This is tax preparation- looking back at the past year, compiling necessary forms, and filing your taxes.Tax planning, on the other hand, is a proactive strategy. It involves looking ahead and making decisions that will minimize your tax liability in the future. Join Scott and Marc as they discuss how effective tax planning can create significant financia...

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14:23

What You Need To Know About Fed Rate Cuts (Sept 2024...

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

2024/09/19

As of yesterday, the Federal Reserve announced a larger-than-expected interest rate cut of 50 basis points, surprising many who anticipated a smaller 25-point reduction. Scott has had several clients reach out to him about this unexpected move. So in today’s episode, we’ll talk about the implications of this decision, especially for those nearing retirement or facing major financial decisions.Here’s some of what we discuss in this episode:0:00 – Intro2:14 – Chatting with David Walker4:14 – Wh...

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13:13

Dealing with Market Volatility

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

2024/09/05

If you’ve ever flown on a plane, you’ve likely experienced some turbulence along the way. While it’s an uncomfortable feeling, in most cases, it often doesn't significantly impact the overall journey. Similarly, market volatility is a natural part of investing, but it doesn’t have to derail your plan.Here’s some of what we discuss in this episode:0:00 – Intro2:14 – Making adjustments along the way4:40 – Staying the course despite turbulence7:22 – Getting better investment performance ov...

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12:01

Tax Planning: 401k Vs Roth 401k

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

2024/08/29

Tax planning might not be the most exciting topic, but it's certainly an important one. In this week’s episode, Scott and Marc chat about the differences between traditional 401ks and the increasingly popular Roth 401k when it comes to taxes. For pilots, the 401k is often the largest wealth-building tool, so it’s very important to understand how to navigate them and how they could affect your taxes now and in the future. Here’s some of what we discuss in this episode:0:00 – Intro1:09 – Sub-ac...

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10:56

Understanding Interest Rates and Stock Investments

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

2024/08/22

This week on the Wealthy Pilot’s Podcast, we’re focusing on interest rates and their impact on the stock and bond market. With recent fluctuations in the market and potential rate changes on the horizon, it's crucial to understand how these factors can affect your financial strategy, especially for those nearing retirement.Stay tuned as we break down how interest rates impact various sectors and the historical effects of rate cuts on the stock market. We’ll also discuss the importance of havi...

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10:24

Election Cycles & Your Investments: What Pilots Need...

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

2024/08/15

Election years can stir up uncertainty, especially in the financial markets. But how should pilots, with their unique financial situations, navigate this turbulence? Stay tuned as Scott and Marc dive into the effects of election cycles on investing, finance, and retirement planning.Here’s some of what we discuss in this episode:0:00 – Intro0:38 – The stock market’s volatility5:08 – Staying invested through political changes7:07 – Being intentional with long-term decisionsResources:Schedule A ...

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65 results

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